abstract - ir.amu.ac.inir.amu.ac.in/334/1/t 2133.pdf · «oi«l doa no met t irit freh ... the...
TRANSCRIPT
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S T U D I E S O N O R G A N I C R E A C T I O N S O F
A N A L Y T I C A L I M P O R T A N C E
ABSTRACT
A THESIS SUBMITTED TO THE ALIGARH MUSLIM UNIVERSITY. ALIGARH
FOR THE DEGREE OF D O C T O R O F P H I L O S O P H Y
IN C H E M I S T R Y
BY
A T M A PRAK:ASH,M . SC., M. phii.
January 1980
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T2133
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Pr,M»$, mHiort 'HEMISTBY SECTION
''•f. No.
ZAKIR HUSAIN COLLEGE OF ENGG. & TECHNOLOGY
ALIGARH MUSLIM UNIVERSITY ALIGARH—202001 (INDIA)
Dated
Tills iB to o«rt i l^ tbat tlie tbesi* i s tHe orlgioal work of tii« oanditeis end Is snltsl^Xs for stdialssioii.
Gathors)
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A C K H O y L l P G E I I E H T
fli« au^or tlianics pr»B«3* Bathore f or Ibis gaiiSaoee sod supervisioD. He i » tliaakfttl to rrof.Mol»8ia Qaresiil and for providing researeti fao i i l t i os and inportaot disoossioas. ne also ^iiltos to ttiooit tii« rosesrch €»o]ii#ag»oa for tHeir oo-op^mtioa*
( t i )
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C O S T ^ « f 8
ACSKO^uissm^ ( t i ) XX» USTOPmiiBS ( iv)
XXX, CSBUiPTER « X
G iERAi. immDimim i fUSFERENCES 4
IV, CHAPfEH - XI 5-%2 mn OP p-fiXftemmffxiioBOi^u^iDc AS A coiou^i^
mmmt 3
U EBBNCES 3%
CBAmn * XIX 43-52
OOK0O9SATXOK OP HfB AiniXME PE^IO&AfB SXrgiXM^mt. 44 RBsours AND msctrssxoii 49 mPER^CBS 52
•X* CHAPTER . XV 93-68 COiOim BMCnON op OXFHEYIAMIHB %im AiOERYDES
EXPERXKEKTAL 94
iiKSCLTS AND DISCUSSION 57 REPBRFNCeS 68
< 111 )
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VXX. CRAFTBH . Y 69^80
O i f S C T I O K O P SOME O B Q A H I C A C I D S ¥ l * m p ^ T m w m t h -
mtmnmMismtm in a c e t i c a h b t d r x c b
gxpEwmmTAt 70 PBDCEDimES AMD B E S U l / r S 7 0
DISCUSSION 73 BEfES^Cl^ 80
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h I 8 f O W TAB LBS
Page
tAsm 1 ( A ) o t r e c n o N i n a c i d i c m e d i i i i * 1 9 - 8 9
KB) DETECTION 18 By^SIC MEDlt»i. 3 0 - 3 1
tic) i^>TECTioN I K K c m - f u t . imim. 3 8 - 3 5
fABt£ It mmmfAL A N A L Y S I S BE381/I?s O F F S B C * 48 i n S&OfBKTAL AKAtYSlS m&Vms OF 48
fABt£ IV x^mt m m rofi p e o i o m a t e i ) so i i r r b a s e ( p s b )
O B T A i i f O ) Fim p . M B Affo Amum pismsBwmw, 49 fABl£ V x^mt mfA or 5 0
TABiE VI x^mt mnA OF A^iULm vmrnwrnm. 5 1
TiiBLE i n i EiiHOSTAL AmLfSIS HCSOLTS OF CO9fI>Oa£0 ( B ) . 63 fABt^ vtu x-Mir DATA mn isucimmummmimmumm
f»EBCBiX>f1AfC. 6 4
HABiM IX X-BAT imTA fOB BXPHGTlAIIIHE PEBdlUDKATE. 6 5
fABlE X X.BAT DATA OF BENZALDBtm-DIFIIlNYlAiaNE
BtDHOCHIOllIC ACID fmUVCT, 6 6
nam XX iUSMSNTAl* A K 4 L T S I S BESlHUrs FOB O O t t P O m D ( T ) . 6 7
TABUS X I I DETECTION O F SOME CABBOmiC ACID AT 105*C* 7 6 - 7 7
U I I DBTBCTION OF SOKE a\«BOXTUC A C I D A T 100*C. 7 8 - 7 9
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A B s y a A C f
|K0l»etliylaiaiiic^en3:8l<l0&ya« ({i*mil) hem used m a colouring reagent for the detection of nunerous coTspounds ana f o r tbe determliiattoik of tbe follotrios oospomtdss
Affiloos , (prtiearF & tteoosSary)^ imptirities in tertiary aroffiatic Qoetoptiotione, otilnosalloyltc o d d , alootiols (tiigber) of the
paraffia serlesf osyl ecetato, o l l y l urea, ollylthiottrea, azc^emsseno, aolsiain©, ai^no peptidases* aaalca©, anlUtie, l^aeotyl-D claeo«»t i i©, t-butylarea, n-btitylaelee, ctooole, cait)lopa L-(«) s<l-hydrazlne-3» ^-dlliyaroKy-o^-sKstbyl byaw^ctausolc actd* eatfeoisal, p-ci^iloro-M-settsyJU aoiMncy eiroga (rottmaiao, BK>rptii»e, codoiaet QOvocGiDe-nCi, ctiXoraeplieoioolt varioos solfonaioltJea ona diaisioodir^enyl, sulfoae), dlsaoc£ioriae» 3t^-«31cIiloroaolliiiet 3,4-dtciiloroiatro benzenf, dulotne* otbyleue tbtourea, glycerol quaTeolatCt Quaiaanlea©, glyclne» liydrazlae» blstamino, bipporlc aoiag int^oles ieol>otymldebyde, Isobatyleoe, l ipids , ssetliyl urea, 2-sietiiyl»3-«iTl-^-^«iooaaoloii€», csfprobamate, oltroso am aso cosspocmdst pyrmirlo acldt phetiyl urea, pbeuyl ti)ioar«a, proliaehyaroxy, pyriaox<ii»itie, pyrroles, prooolae, n»sorcl»ol , solplionamliles, stilphatfilazole, s u o c I d I o dlaldcbyde, tropic acid, thiourea, li-tyroslue, %,6,8-trieeiuyl azul«t3«, tryptopJian in cer.?il9, urea In blood, trrea in water, uf«a in s o i l , tfroblllBO«ea, urea foraml<}ehyUe reain and vanadata etc*
p-nnit oondeaaes (sctiene-5) i«itli aoilii«B peroblorate to give red needles o f protonated Schiff base* the forvation of Sehiff ba«« bas been proved by eleneatal, n*«*r. , l . r . and x-ray analyses, fbe
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f\t
X o
X o o • OJ
X z a:
o X + <vj rO X o
I X o
< CO
X o if)
CJ LJ ^ in rO <
X CO o
tn
UJ X o cO
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( I t )
4M>loar of til* protonaied Seblff base oootaniiiaM with pareliloric «oi«l doas not m e t irith free anlae to give tb« S ^ f f i>sse« It rm&etv vitb free anlne In tiie presenoe o f an acia. Oaprotonated Betiiff Daee (yeli<»w <HHipound) cauoot he obtained from the reaction of p*DAB iritb animi salt* Since orange coapotiaa may be tbe oontaminatea pro toasted Sotiiff boaec* red co^pouiia ie o Soliiff baac i!istluetto!3 ismmg mm^ di and polyaailiies siasr not be laade on tbe basis of tbe coloor« As a result aoae of the earlier rmarks on ttie p-mB'-aaines reaction seasi to be doubtful apoa raieleaditig.
Oipbenyladiae reeots vitb olSelsydes in aoidlio soltttions, DiptionylaiiiiiG salts (bydrocblorideg sulpliato aaS percblorate) react vitb aMcEiydea diroctiy* Hiese reactions may be divided in two classess tbe f i r s t i s baseil on tbe Sormmtton of very stable teruary iraiaitsi salts (8cbe@e*6) andl tbe second class depends on tbe formation of bi^bly tmstable (scbese-7) and deliquescent ternary isiniiai salts, latter salts are aotosidized witb «1»»ospberic oxyi^n to give <3eeply coloured ooiapoun^ wbicb can be used for tbe sensitive coloorisetric detection and detemioation. Hie teraary iainiim perc^lorate obtained any be need as explosives.
p-mfe in acetic anhydride can be used for tbe detection of blgber caiboxylic acids on paper ebromatograw or TtC plates* fbe liMit of identification for c i t r i c , isocitrlc* oC-ketoglatarie and oxaloaoetie acids i s iO/m»
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•o o 4-X 4-X •V —
o o X
oc
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I/)
I/I II 3
X t o
X o O M o z
o < CI o
X O z 0 01 £ o u OJ -J in I
Ul £ Ui X o
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C H A F f S B * !
OBWEmt HfTROPaOTIOW
Hit «iiftl3rti«8l «iii«M&»try Awlm vitli d«ttott<m» a«t«nilnatlon and ••parsttoa of tons or atom or m»1«qu1«» or ftmotlomil groiipo in a
of ottforlolo* Analytioal otiaaiatry includoa not oaly tlia oanipiilatlTa t«chnlqu«» l»ot i t oiao dtala witli ttio tbaoratioal oonsidarationa upon wtiiob dataotiima» datanniiiationa and aapamtiona ara baaad* Sir David N* Bt»a^» in hia 1969 Htliar Award addraiOt praaantad analytieai ehaaiatrr aa a point of viavt an intaliootoal attitodaf a way of attaoking tiamlml problestat a diaoipUna in i ta own right. Iafaot« in broadar aanaa analytioal obaeiatrr deaia witli tha taotmiqnaa wliidi jriaid any type of infomation about otiwiQal ayataaa* Erary otoaaiat ia an analyst in ao far aa ba aaeica infomation about obaaiool ayata«a« but tba anaiytioal oba»iat ia diatingoialiad by bia priMry oonoarn tritb tbe davalopaent of exparinantal aatboda for obtaining that infomation* Ba aay bava to daal witti prOblava froB infinitaaiaal aaotmta of iaporitiaa in tranaiator aatarialat to dating arobaaologiaal aaaplaat to problana in foranaio obaaiatry and froa a aartload of ora to tba ganatio aatarial of a frtiitfiy*
fba abaaiaai analyaia* in a Uaitad aanaa but aora praeiaaly aan ba dividad into taalitati^a and qnantitativa analyaia* lha analyaia of oigania ooapoimda ia quita ooapUoatad but at tba aaaa tiaa i t aonatitataa a vary faaoinating and fondaatntal atody. lb a abaaiat ta abaa aaat artdit ia daa for tba davaiopaant of organio analyaia ia rraf.i.P.NalUkaa'* m tba ama of qoalitativa analyaia
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vartoua oiiMil«^ •• a* •paeiroaeopio aatboda ara aval lab la« AaKsngat thaaa aatlioda tba apot taat taQbaiqiaa la alaipla and tnaaipaiiatva* In tlia orgaBle prorinea of apot taat analyaiat tba inlo aol<S waa dataotad hy Bqgo Sobiff^ in 1899* SlBllarly for Qoaatitativa analsrala botli oliealoal and inatronaiital aatboda have baen uaad* Howavart gmat atrldaa bava baao aade in recant yaare In tbe appUoation of apaotroaoopy to the aoiottoa of aaaljrtioal problasa* fba inatruaental aatboda ara rapid and aenaitlva* tbay bave beooae readily available analyttoal toola. In itiyaieal aetbodat a fav ailligraaa of tbe ailbatanoe are required and tbe aaaple oan be recovered after analyaia, Btit they require costly and aopbiatioatad inatrusent end atcilled operator* However, tbe ebeiaioal aetboda are aiaple and inexpensive* Utey can be uaed ae a f i e ld teobniQue. lb us every teobniqne baa got i ta own aerita and deaerita* Hie ooapariaon of teobniqaea f o r the pnrpoae of analyaia can be divided on the baaie of aeneitivity and aeleotivity* the aenaitivity of aetbod te l le the ainiaua aaoont of aaaple required f or i ta aeaningfol deteetion or deteiainatioat while eeieotivity te l le a or i t ioa l view f o r deteetion or detenaination of a partioular atibatanee in a aixtnre*
fhe advent of eolour reactiona aakea i t poaaible to work oat nuaeroua eeneitive* eeleetive end uneqaivoeal aethoda of deteetion and deteiainatioa* fhe firet eolour reeetion, llietcel*diaetbyl«ly* oxiae reaetion, waa intreduoed into quantitative analyaie by l*.faohqiaeff^ in 1905 end O.Brunk^ in i9i%» Mowadaya oxganle apot teete baaed on eelour reeetiene are extraaely naefni for the deteetion ef orKanie eoapeuada er oigenle fimetieael greupe. Fer qiientiUtive
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tii» •p«otropliotoa«trlo M«ttiodc mr% being on Amiag»t •i»«otropli0toa«trlo Mtbods, visible
^viree-rpr |»r»f«rre4 beoatiee of i t s s i «pl lo i tr« I f i t i s
<leeired to analjree the oxianio cospouade in the vieible epeotriMi* tbey eon be oonvertetf to derivative* wbiob poeeee* etroog ohrooaoiiborio groope i»e« oolotired prodnete* AltbotiqSli oolourisietrio aetbods ore oaosf tbe earliest inetrtanenta I teobniques but eveo today they are ooneidend «e a top raolcing netbod due to tbeir overall at i l i tr* Varioae boolce^ and revieve^ bave been ptibliebed on the util ity o f ooloiir maotiona in ois^nio analraie* A atirvey^ of tbe Uteratare atiggeata that steohaniatio atudiea are iwportant in order to eatablieb tbe f o i l analytiooi ut i l i ty of a ooloar reaotioa* therefore* in tbia tbeaia tbe following troffc on the ooloar reaotiona of p^disetbyl* aainobenialdeiijrde baa been done* Ibe vartoaa ooloor raaotion* of p»di«etbyla«in^eaaaldebyde are reviewed in Chapter t%t p*diHiethyU aainobenaaldebyda-priaary aiHtne reaotiona are diaetsaaed in Chapter xxx^ p»diaetbylaaiioobeiitaldebyde*aaoondary a»ine reaotiona are diacuaaed in Chapter XV and the vae o f p»diaetbylaiiinObenaald<^yde for the deteotioa of oiianie aaida ia diaaitaaed in Chapter
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R E r E R E K C E S
1. Gilbert *QtM»titatlve Oieatoal Analysis % B«rp«r and Brothttra* Pti»U«liers, Haw ttork,
2. WliHoii,Barold r*, 'Prlaeiplaa And Matiioda of Cbeadleal Analysia*, l»rtiitiea*i}aU» ino.Englewood Cliffa» N.J., O.S«A*t
5« SaaiyO., *QiiaUt8tiva Organic Analyaia* An Elaaentiy Coarae In tha Ideatificatleti of Ox%anio Cmtpitnida** Jolm fTilley, i923« Faisl»P.« *Spot f «at In Organic Analysis*, Elaeviar P^liidbitng Conpaay, london, I960.
5* Saireki,g*9 *^otoaatrio Oiianio Analysis % Part I , Willy InteraeienceSf iomon, i970«
6* IlBttior«»B*S*, Moba)amad»A«, PrakastiyA^t Rasnarl»8;«« <l«C9iefli. Scicnoaa (In Praaa).
7« A l e x a n d e r , a n d BQtler,A«B., «l«C«S*Perkin XX, 1976, 696*
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5
C f l A P f g B * ! !
PSE or p»DIIIgrHYUmitOBEWZAU>EOinDE AS A COtOtmiNG aEAOm
p-diMtbyl«ainol>«nxa l(l«hyd« (p-SAB), Ebrliob*« • vry important oolourlog mgttntt an ifi4ie«ti«ii of tlit* giT«ii
hy 165 r«f«rtiio«» d«alitii onljr vltb ooloaria«trlo d«t«rnifi ftttOB at Uatad in ^ e l>oolc of Ve^dalale and saieao^* Many of tba appUoattona of p-DAB aa a dateotor in tbe f ie ld of papar and tbiii layar ebroiuitographr bava baan daaoriDad^f Hovavari tt iiaa baeoaa of graat aignifloanoa baoauaa of the faota thm% (1) tbe turlaa of iQdividoala auffartog fron aosa payotiotto lllnaaa oontalna ttryptopyw rrole i^ieh i s tsmm as t!i« ^native feotor* lijf virtoa^ of ita reaotiona with p->mB« (11) for testing of Ik^-ver funotlon, diagnoaia and aatiaatioit of tba datoxioatioa of allkyl baaaanaa and drug a tiia datamination of bipporio aoid® liaa baan a»da witti p^mB and ( i i i ) i t piara an iaportaat rola in d i f farent iat i^ battraen aarm eri^tioaa and troa aaarlat favar^« lliaraforat i t vaa thought worth«hiia to aiMHarisa tha ooloor raaotiona of
In tbia thaala tha prograaa in tha uaa of p DAB aa a ooloarii« faagant upto rabmarr ^979 ia atiHMrisad« An attaapt baa alao baan «ada to rtvlaw io briaf tha chaslstry of tha colour raaotiona aa thia kttowladga ia raqairad to davalop aaw aolour raaotion or to iaqprova tha raaationa alraadjr kaawn. Baoausa of tha iapoaaibiUtsr aa wall aa tha iaadviaability to doaavant all pdblioationa ralatad to eoloar raaotioaa in thia briaf nriWf aathor haa triad to inoloda tha aora
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r-\ o
t«port«at •tndlea, siitojeot only to porsonal pr»judio»« and, therefore, reoogoiae b i t failH^tUty of oalttine son* Important rafaivneva*
Pataftimttoti
ttt followtnc eonpotmda Dave been datamliaed for uaiog p^mB aa tba oolottnag raagant. AKlnaa^^ (priaary & aaeoiidary)t leptiritiaa In tertiaiy aromat&o aoatopbaiiOBt**, awinoaalloyUo octd*®**^, alec^olfl' (bigbar of the p a n f f i n aertaa), asiyl aoetato't a l l y l araa^ allyUbioarea^', aeobetisane^^t aatatdlna*^® anioo peptidaaea^^t aaoleo©^^*^, anlllna^^*^^, H^oootyl-D glmoBmim^^^ t-botylnraa*®,
otneol©', oat^iopa L- ( - ) ^^dibydroaey-oC^mtbyl hy^roeinamie oarbosal^, p-ob2oro-N*iiettiyl»
aotUoa^t druga^ (rotuodiney siorpbinc, eodetiiG« novooaine^llClt obloraa^bentool^ variotia •olfoiienl.dea and diaatuodtpbooyly anlfOBa), diaaeoharida^^» 3^4-dioblorofttiiltiia^* 3i4»dlebIoroiiltro bansena^t dulolna'*, atbyloae tblouraa*', glyoarol goaveolata'^, giailaattleaa*^^'^, glyolna^^*®®, bydraaiaa55»3%^ bippurie aoid^, Indolaa^', iaobtttyraldabyda^^t iaabutylena^t Uplda'^, watbyl iiraa*'^, 2-«atbyl-.>.aryl^4«Qaiiioaaolonaa^, Mprobaaata^^, Btiroaa and aso ooMpotinda^^t pyrinrio aold^^t phenyl tiraa^'^ pbanyl tbioaraa^'* proltnabydroxy^'t pyrtdoxanlna^'®®, prooatna^*, aaIphona»idaa*^'*^» aulpbatbtazoia'^t aueeinio dlaldabyda^^*^^, troplo aold'^, ibioturaa^'t Utyroaina^^*^^ %»6«8»trl««ibyl aattlana^^'®®» tryptopban" in oarala» tiraa in b lood '^* '^ '® , m a in tratar' ', iwaa in a o i l ^ ' ^ , ar<^tlino«an^,
nraa forvaldabyda raain^'*^ and •anadataa'^ ato.
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7
tfUMm
NWMiroii» eospoimds colour witb p»MB and i t bean oMd for tbeir dotootioo* Hioso ooapoui^s oro suaoiariBod in tabloa iA» ID A IC«
tba olaaaifieation of tbe above colour raaoiiona ia ttifflonlt booauaa for a particular t«at one baa to paaa tbroiigb aiivaral atataa* For axeMpla» ansafs ttra f i rat coiidotiaad with aoatr^aoetooa to give pyrrole darivativaa and tba psnrrola aariirativaa ao proauoad give colourad produota witb p«>MB» fbaraforot waa oonaidarad wortbwbile to olaaalfy tba raaotioaa on %bo baaia of tba ftmotional group of tba taat atAiatanoo* fbia type of olaaaifiofitioi} bad alao been isade hy
Strauli & Avarall^*
i» Bydraginaa aoQ ralatad conbotinda
p-EAB raaota witb bydraaine , in alicaltna aolation to giva a canary srallow oryatala of an asi ne (i> inaolubla in vatar and aligbtly aoltibla in aloobol witb oi.p. Iba asina ( i ) raarrangaa in acid aolation (Bcl) to a qoinonoid atructora ( i » t ) of dark rad cryatala of aalting point tbia asina-quinonoid atrootora arrania»ant ia ravaraibla and i t aooounta for tba axtra»a aanaiti¥ity of tba mtbod for tba aatiaation of bydrasina* So»a loaa in aanaitivity^* oooara witb aiAiatit«itad bydraaina baoauaa of tba laaa niartiar of poaaibla raaonanca atrnettiraa* llaeantly^^*^^» i t baa baan raportad that eaftainaoatio acid bydrasina and anthrapyraaola bydrasona raaot aittilarly*
![Page 20: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/20.jpg)
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9
a* A»ttt»« and C0i»oana»
(ly Pfiwary
rr imry ••lots ana tbeir eoiidcQM with p-CAB in sireng aoitf colttttoa to jritid oolonrtd Selilff*» 1ti««« raaotions «aii aifio 1>a earrtadi out in lUia voltea atata* Koaoaaitiiaa fiiTa fallow oiiroaogaiia atiila ai or poljraetiiaa giv& orange ektvammB» Prdbahly
in di or polyanioaa uora tbao ona m^ RTotxp taka part in oondanaation ao ttiar giira c^row^an aSiowing radi abift* fba aanaitivity of tliaaa raaotiona oao ba ai^anoad in tbraa vaya» ( i ) Uka by^rasina <^row%ana> i«a« by protonating tba obroaogan ( l t2 ) to mmmn^e in gtiinonoid atruetiura ( i . 3 ) » ( i i ) tba Sobiff baaa ean be miaiaad^ witb atMoapbario os^^an to giva a natarial o f oora intense oolonr (in tbia way tba aanaitivity ineraaaaa oonBidarabiy>t ana ( i i i ) aosa o f tba Sobiff baaaa oan f o m aetal cocplex*'® o f wery intanaa ooiottr* fbtta ^ a aMaitivity amy be inoraaaail*
Rotrairart tba cbaadatry of p-»mB»pnaary aninaa raaotion oan ba fortbar atvidad in tbraa groupa* (a) Aainaa oontaining Ifflg group or gronpa oondanaa witb i t to give Sobiff *a baaaa* f o r axffiaplat aniline eondanaaa vitb i t in atrong aoid. Iba sobif f *a baaa ao foiiMd (i«%) abaoiba at n« ( m i * i i ) and ia vary atabla» i«a* doaa not oxidise vitb ataoapbario oxygen*
Sisdlarly aainodipbanyl aaina^'^, biataaina^t pyridoxaaine^'t N,ll»diaatbyl<.p.pbenyleae dieaine^^'*^^^*^'^* naptbylaaina anlfonio aoidt naptbylaainat edianiaidinat bansidlnet Miinepyridine* i«aainoantbra» ftiinina end %»aaiao-l,8>aaptba%iiiaone yield eiai lar aaloared tai i i f f 'a baaea'*
![Page 22: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/22.jpg)
10
(li) 9om prinaiy aaln* d*rivatlVM eonfain NB group feat tfo not prodoe* oolonr po«»i1>ly diM to doaetlvatloo. for oxaaplo, o* or wT or p^nitroanl llnos^^' do aot prodoeo ooloar •Itliex' In oold or in mini •qiuioao aloHollo tolation. nioy do not produoo colour oven In tlio presvQOo of accoitlo aold* HfHrovor, i f to tHe pn»aenea of aaoorbio sold tbe altroaiiiilii«a*p*BA8 niztiiraa arc tiaatad to drsmaaa, only p*nltroaaiUQ« glvaa a rad ohronogan (1«5)* p-nitroanlllnaa ia radQoad bjr aacoil>lo aoid to give p-phenylcne diaaine vtiiob reacts with i t to giv« otiroMOgon (1*5) •
(o) Prieary aliphatio oadiiee end orosatio aainaa can tie oliaraoter-QB
Izad and datonilnod by tba aattood of SawioM ai^ JcNtmaon^* tiytlrolytio olaavaga in ooetio aoid sedioM* 2t5»diBiatbojiy«totr«l)ydrofiiran givaa auooinic dlaldetiyde i^ioti, t>y raaotion witb prieary anioo group, yielaa a K^atlbatittttad pyrrole vbiob ia tban davalopad witb p-ms* fbia prooadura laada to oaa tbo Moat aanaitiva colourinetrio aatimtiona of tbaaa oowpouada*
Uatlioiiiytatrahydroftiran aan ba aiiiatitatad for tba disatbojiy darivatiTa and tba pink-oranga to pink-violat oolour dairalopad afforda tba abaoifbanea valtia 0*30 with, for axaiqila •t btityla«ina« 2«i Am of aniUna*
<ii) Saoandary mminmm
Saaotion of aaaondaiy a«iaaa or tbair aalta witb aidabydaa or katonaa ara iaaa fa»ili«r. Aooording to Faigl' dipbanylanina raaota witb ia tba aaaa way aa pri«ary aainaa raaot witb it* Quraabi at ai.^***' bava pointad out tbat dipbanylanina emlbtn%w witb it only
![Page 23: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/23.jpg)
1 1
In prt9«iio« of strong aoid (1*6) • 8oIi<l dlpbooyl mwAm
bydrooblortdo^" aI«o pro&uifm eolour vttti solKI
itMtd»a ana CoTOoaatta
St tias Dean roportod tbat onino group of t!ie «nia«» do«» not react wltb {kMO* 8ovavar» t>y iioattng I$*|stieiiyl«tti3»atitfitad awldas wltli qoaoiatiia oartiOBata^^ to 2^*0 (for altpbatto atuS arwatio antdoa)
tlia aalllii« ttiat i s produced la dataotad* On Haeting with aumaootsa aiilpbata tetmttydrata at t30*Ct only oUptiatio aallidea eliiainata aniUna ao tHar liay t>« dlatlngaif^ad froa arf»atto anilldea by thta
prooadiira* flia aotiya vatliylena group of tba bai^iturlo aold^^' and tbiobaf^tturio aoid**^**^® raaota wltti p-mn to give ohrotKogen <t ,7) . thus tbia taat ean ba naad to diattngtiieb parent baxbitnrio eotd fioa
tholr darlvativaa.
Die prloary arosatAo tmlno group of attlpbanilaatida^^ ooa&lnaa
wttb tt to giva oranga S ^ i f f * a baaa (t*S) bot la aoidlo aadiun the aidno group Unkad vitb SO^ doaa not taka part in tba raaotlott,"
laraaa. Ata dartvattvaa and ralatad aoapoonda
tJr%m and aubatltutad tiraaa^*^''^'^^^ for* oolourad oondanaatton produota (t»9) with p*mB in aoidlo aadimi* flia aanaitivity of tba ooloor raaotion la «ora in iaopropyl alellol*BgSD^ aadiiH than that in atbaool^flOl laadiaM.
Although thia proaadura baa baan vidaly uaad for aattara
Of oUnioal tba obaaiatry of raaotion batwaan
P*IMB and aidiatittttad nraaa or tbiouraaa baa not baan folly ondaratood*
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1 3
fiQ I n tho v iew o f Sarrenacttsen liip f r e e a E l o o p.roi3rp o f ureas o r
I b l o u r r a s r e a c t s with c a r b o z ^ l group o f p-D.%B. lb© v a l i d i t y o f I t i ! !
Uas b c o a cXaifflGd by lioimgy aad P l a ^ y feocaase isany <somp©tn«3Ri
l i l lpUenyiurcaf a c e t y l t l i l o u r e a « t o « ) t b a t p o s s e e s i f r e e antino group
do not glure c o i o u r witli i t *
5* P y i o t i o n a l f^roupa i^itti a i t r o g c o - o i t r o y ^ e a l i o k n ^ c
Azo o r hf&ix&y c o ^ o u Q d s ^ * ^ ( S t 2 » i } c o o t a i n l o g oao o r store
fhmn f r o u p s e r e roaoccd t l t b z t a o and RCl ( a c i d s o l u b l e d y e s ) t o f i v e
pri0jf»ry o r o m o t l c malncs , bydroaeobooEene andercocs on iQtramole&ular
orran^cocnt t o b o n s i d i a e s ( 2 * 2 ) • Its ffllaerol acid, diozooltjsj cotspouaci®
( 2 . 3 ) arc rodaecd viith t^imr^G o l l o y and c a u e t l o a l k a l i to g i v e
h y d r a g l o e s . T i o s e products produco c o l o o r w i t a p«E\B aa d l s c u s s c d
a b o v e ,
6 . H e t e r o c y c l i c n i t r o g e n ooatpoaiidB
poimB ti«« !)«en a v e r y popali ir oolourit^^ r e a g e n t f o r
p y r r o l e s ^ * a n d i n d o l e s ^ f o r t b e l a s t seven d e o a d c s . I t i s
an e x c e l l e n t c o l o u r r e a c t i o n ( 2 . 4 ) f o r d e t e c t i u u b u t t h e d e t e n a i n n t i o n
cannot b e n^ide ah the c o l o u r f a d e s rapidly*^* I n d o l e , s k a t o l e
fltetiiylindole) and tryptophan ( / ^ ^ i a d o l y l a l a w i a e ) r c a c t analoi^ously^
t o p y r r o l e whereas c a r b a z o l ( d i b c n z o p y r r o l e ) does n o t r e a c t *
R e c e n t l y o t h e r cbroaoicena o f t b i s t y p e %ith i t 3 » ^ * t b i 0 K 0 l o f
p y r i a i d i n i u a p e w i b l o r a t e ^ ^ * rtiodanine-piperaaine^*®, 6 ( o r 7 ) - b r o M o - l ,
2 » 3 - t r l » e t h y l p e m i d i n i t i s i c b l o r i d e ^ ^ ' and 2 « > - d i » e t b y l t b l a z o l i ^ i i n e s
and t h e i r 1 , 1 - d i o x i d e ® ^ * * .
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1 5
7* Mitao poiyp«ptld»» ttM prot»lp»
Aaino groap o f on { » ino aeid dots iK>t r«aot « l t b p«DAB»
f o r •xanplft g lro in« does not prodiKso may colotir*^' . However, fwino
acids can be ctiaracterleed and dettniined by i b e aetbod of SAtflCKX go
and JC KSON* *" described tmder tbe beading prinary aaioee*
p-nAB«>tr3r^topban^ eolour reaction i s tooim since long* i t
bas betn i>rop08ea tbat tryptoi^aii reaoia anali^ottsly t o pyrrole•
I t baa a lso been eentiimed that tryptopbaa ooadensea witb
p-DAO to give a S o b l f f ' a bate ubicb onn be oxidised witb n i t r i t e
to a blue dsrosogen. Ibe nature of tbe b l i » (^rono^en bas not been
ident i f i ed so far*
S* Sugars
Msino sc^ars, glucosaalne end cboQdrosaaine» condense vitb acetylacetone to pyrrole derivatives^^^ (Elson-Morfton reaction), ^ i s substituted pyrrole gives ma intensely red oolonred d y e - s t u f f (2.5) idiiob serves f or colouriaetrie detection and detensinatioa*
9* amthetie p o l v e r s
Crsa produced^ (3*8) from tbe bydrolyais of urea fomaldebyde resins in aetbaaollo bydroebleride acid gives Scbiff*s base. Otber nitrogen poljraers (except aelMiine) produce oolour s ia i lar ly . Bowevert in aniiydrstts solntien (aixtMre of glacial aeetic acid-aeetio aaiiydride) area praduoed froai urea fonMld^yde resia gives a bine oolenr ebroaegea and tbis test sseas to be sped f i e f o r area feras Idebyde resins, fbe ebeaistry of tbis rsaetion has net yet been studied.
![Page 28: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/28.jpg)
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ABtMl ftl»r«»' oan 1>« diatingfilshcd from v^etalil* fibr««
a« ttia mtlaal fil>r« gif«tt pyrrol• dtrlvatlva* on th^rml dl«oo»po*ltioii
f roa pmtmtn eo«]|^eiit wuicb glir«8 eolour*
10* Hitrogan Cowiomiai^
IkIMB roaots wltti to
giva a i^lloir oltroaogaii Otiior aroisatio oitroooffipounda^^t (S«7)» irtiieft do aot prodooo e^lourp am t>© oDaraotarlaed mad aatiwatad eolouriaetrioailsr after thalr radiiotton to oorrespondiiig prtoary aiiloaa Djr potasalia boroiir^rlda in the pr»eaiica of palladlan.
Sifailorly 08 heetlog ttitlt atco gives pyrroles i^loli cao he loped wltlb
11* Hon-nitrogea oogpoimda
Moat pbenola^^*^^ do not give oolotir wfttb novever» and ita 8*«etliyl and %*mthyl derivativea^®
givea purple eoloitr tn 2N BCl* But liy6*dUietliyl-re8oreinol gives a
pale pink eolour ubieii develops very slowly after nany days atandii^*
Itaptlioresoreinol*^ and pliloreftliieittoft^^*^^' ^ebave like resoroinol
end give yellov-treen and red^violet oltroMOgens respeotively* fled*
violet obroMien disappears quiekly* Mssereinol oaiboxylio aeid doee
not give eolonr beeause of deactivation of tke ring* It seens that a
reeoroinol requires a free % or 6 position and tbe abeenoe of an
anooapensated oartonyl (deactivating) group in order to give oolour*
Aaphoterio purple oonpound lies been ieolated fro« botb reeoroinol and
8-*ettiyl rssorsinol. No solvent suitable for orystallisation were
found and purifioation was offooted by preoipitation in aeid*base
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1 7
system* On tbe t»asis o f Qjl4»eotal» I r and uv analysis , cbroeogeus
(2.8t2«9>3) bave been propossa.
f Q "lA
Aasulcae • naaely Qimia/olcac, aauieoc, vltlvazuleae etc# cOffi1>liic idlttj p-ElB to cturGQC eo (3«1)* stmiior chrotBogoos ** aro (3.E)t<3.3)#
It is also imi ia flint ana ncctlc aolif drido Iv c the omazti colour «?itibt o-tJyUrot'y t ensolo, lilppiirio ana phenyl acet i c
QCitls, beossoiCt bippurio and p&cnyl ecotic act<3 ana p-bydrosy cimiomoyl glycioc* Xo o ooous HCl p-HtO givos blue colour witb 5-bydroxy iofiolo ocottc ooia^^ . It® solatton la pyrtmuB ai-ves a
8
yellow colottr iiitli Otppurto add solotion l» iHJctio oialiydrld©. On tlie basis of f •L.C* epcotropliotOTOtesry it ba» been propo seCI tbot tb© product consists of 2'-iphenyl-'4*Co<r»tiyaro»y syotbyliacoc) osQEol-S-one (p-slieJothylMinobons;©!) O3i:aEOl-5-0ne(3.5)
etn& om unknofeii co^otmil correspona to Rf value Qod 0.70 /I SQdk • and 0.48 sad 990 and 438 na ro8|HBotively»
ITeace i t i s obvious tbat in-IIAH g ivos co lour reaotioa witb
a wide vsr i r ty o f coapounds, « l i t t l e i s tniowo about tli® cbevistry o f
I t s reaction, aad i t s oev colour resct ioas f o r tbe purpose o f detection
ai^ detemiaation ID tbe area o f a i r po l lut ion , b iocheaistry , c l i n i c a l
cbeaeistry, pest i c ides , itioleouiar biolo,^y etc* can be developed*
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1 8
o fO ro ro
to to
»n to
<M
z I \D O X o o
D'
X o o 0 1
o 0 1
X u H X o
6 z fVi ««
to
X ,o o X I o - o o
IIII o
{ Ui Z UJ X o t/>
![Page 31: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/31.jpg)
T IBI : I A • mtec t l oa l o Acidic MctUtm
1 9
s i . No.
1 ———- — Cotapounds Colour
i """" ' ••' -^leaimi
^
liefereiiC4
1. fmiHne Telloiit t o Orattgo
CtbaMOl-Aoia 65
2. AQllioe sdiptiate Telloif t o Orance
Aoetlo Acid 3,66.67
3. Allnfiatle ana oroffititio a^ltaes Cprlisaryt^^coi^d* mry astS tertiary)
Yellow to Or»»ge to Gea
{:tl2aiiol*Aoid 17
4 . ritil^lsli purple
I'oliiMfiJe-ngSB^ or
aold
68
5. ^ oAIaslQe Pale of»i%e m •
6. Ar^lntoe Orange m m
7. -Aslnobotyrtc atsl^ Pale oraxi^e tt e
8. Aspurtlo acia Ortioge m «
Alloiiir#OQliie Pale purpl© tthmoumi m
10. Adenine Bloc to
upon stanAliig
Tolttea«*aold m
11. Actenylie iicitf Blue to « Bronolsti opon iitaiidlng
•
12. Allantom Yelloti t o pink
Ethanol-nci 69
13. 3-A»ino tjlraell reIlow • •
14. l*Ae«lyl tryptopUaa Violet • 70
15. Aaino {Aienolft Orani* m 65
![Page 32: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/32.jpg)
X A €olltli»t«d)
2 0
I' Colour SI.
MO. CMfpotmdls A»f«reiie«
t6« Aatao «9ceept those ooatalalsNI COOH gro^p on the •aige onifioii
17* p-aalno 8aXi<^Uo aoid 18. AroB«iio stilpboxiio
aoida
• Aotdi green
S0« Aoid yellow 21* Alanine wBtnopoptiaes
Anisal tihre
23* Axo 1}«iizeii« pHei^lo by«r«sln« solplioiiio ROid Btnsole acid bydraslda
25* S-(baasylodylaaiiio) •thaaol
26* 2-(1)ansyloaatBo) •thaaol
27* Banio ( f ) QnlaollQa t»
28. Bliirat »
29. Baasalaaitta m
t«llm to Orange
Tallow rallow to
Bad t o fsellow
Orange to
gtbaool-RgSO^
Ethanol-HCl
m ^ COOH
HCl«>2:ii Pieoea
BCl
Bark v i o l e t QCl
m9p Had Cooo.BCl or Bloa
M t o pink HCl flttoreseenoe
M
Had
lthanol*fiCl
Bad toluaaa-aold Pale Pttrple Etiiasol^tolaene
aeld Tallow Pale Orange Tellowlali Toloane^aeld Keddl* Farpla ithaaoU-tolueae dlaalpated by aeld afltatlon
71
72
73
74
75 5,76
77,78,79
80
Tolaene^aold Ethaaol^tolaaae aeld
68
*
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2 1 X A C«itlQtt«d)
T T SI. Ho.
Coapounds Colour ff«dttlM Raforwnoo
30* Bartiittirlo aoid
31»
32 m 9*lleiisyl<ncytry|>tamine Bufatenicte
tryptamine
35. Citrulline
36. Croatine
57. CrestInino 3 i . Cystoino 39* Cyotlno %0. Caffoioo
%1. Cjrtoolno
42. Cytidine
%3. Cytidyllo acid
Tollow to Bttmaol-HCl pink Orange to Cotio.QCl rod flooroscoDoe
Violet • •
» n
Pal© Orange
Yellow Pale Purple
Pale Porple iDtenae Red Pale Tellow Tellov Red Oraoge
Bloe to Purple Dark lavender aeddlati Mng
Pale Lavender purple
«
Etttanol-Tolueae ac id Etbanol BCl Etbanolotoluene* aci
Toloeneoaoid Ethwiol*tolaene acid 1^1uene*acid
Etteaao1-toloene aeid Tolnene-acid
m
Si
70
68
69
68
68
66
![Page 34: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/34.jpg)
23
(7iil>l« I A continued)
T SI, lle^itm
Cami^or
Cor::.© r e d
Orange to
uaa to Tellov
t«2*^ol<^ept6&detUone Violet dioxide
Othanol-ftcld irtolet
ncl^m I'leoes
Benssese CCl COOn
47. ta^Cyelobexaredlone (Sloxlisii
48* Cailjoaal 49. Dtphcaylcaaioo
n m
50» fi,K-aiescttiyl bf^ozyl-n®lne
Yellow fled lots OgGO to Ettianol OCl
Darft Green Bmwai.^ TolBoo^aoia Yellow to rtbanol-'Poluen© Greea aoid
rtbanol-fiCl
51. !?,S?-alhexyltJenaorlasiliie 52, K,!i>dlUeptliyZtoea%ylwiine Bli»e to
• l o l « t
55* ll,!<-4itfiopropyll}en9Byl« V io l « t to aaino Bid M.H-dl^utyl b«ii3Ey l imine
Violet to Bed
55# !I»?l-dlootyl beazyleitiRe Blue
56* 2*(dietiiyleniiie} Derk !Md ethenol
ttianol-{fCl
65
3
3
26
82,83
68 t»
80
lYlbydroxypiienylalaaliie l^ele Ptunple Itbenol-Toluene eoid 68
98. Modotyroeine f a l e Twrple *
59* I%)eiifcolio ac id latenee tted *
![Page 35: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/35.jpg)
(f)a!>le I A Coatlotied) 2 3
T S i . Ito.
Coapotinas Colour Reference
60 • 0itoy<lroor0tic acid
61 • Dibydroaraell
62* Dihydrot^ymine
65* Otmetbyl tryptaadtne
64* Mieethylglyoxlee • etbyleoe diaisiQe
dic^Ioride
66* Oibaoolaitioe
67* fl-ethyl trypteato© 66. HosiQOi^lllio-
granulocytes
Fluoreseelo oiilorldo
70* Gionatic
71* Glntnorln*
72* Olutattiioae
73* Glyoln«
7%* Gnaulne
75* Ciianyllo aeld «
76. GtHiaosia«
77* Gaotriala j|e«tyl
78* Gnatrlsin
tellow to Ptak E:thiiaol-HOl
Tellow •»
TeUow
Violet
Yellow to ©roi^©
Violet
eed
tmaoo l -nc l
Tolti^ne-aoldl EtHaiioi-toltieae-acid
Ctbanol-OCl
mumm. '2
nci-zoci 2
m «
69 n
3
3,66,67
68 m
70
87,88,89 Pale Orange Etbanol^tolaeoeaoid 68
Bright Oraage
Oraage to Yellov
Light Furple Riag
Beddith Tract o f niog
^ddleh
fStbaaol-Bg^^
Tolueae-acld Ethaaol-tolueaeeold
Tolaeae-aeid Ethaaol-tolaeaeoaeid
Tolu«ae«8cid
Sthaaol-BCl 90
![Page 36: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/36.jpg)
24
(Table I ^ Continued)
Si, KO,
Colour Meaiisti
79* Oallic acid
80. Hydrogen peroxide 81* BoiE cirstlxiei
82. C{0!soo3r8telne 83. Rofsoscrino 8%. mstldlB©
85* Bydrocsj^roliiie 86« C ipporio aoi^
87. 5-Hy<lro!!Ey«K»netiiyI tryptAssine
6S* fl-acifl
89* Oalltioiciog@ii8 90 • 5-%diroxytrypta»lne
Isooicotliie actd Hydrazlde
92* leoletioiue 93* Is^ar^itvr lc aeld
Inaole m
95* Xsolitttylftlooliol
Orange to Violet
Orooge
iQtGQ^e Eed tl©ddt8b
Orange
Yd lot? Violet
Orange to l igbt yellOKT
Violot ms to Pink fluorescence
Etfeonol-flCl
Conc.Og^^ Ethano 1-toltme-e^so^
s
Et{iaiiol-ncl
CIljCOOH
Etiianol-BCl Ettianol-OICl fici
t'ale Oraoge EtIianol-BCl Tellow to Pink • Violet Sea to Violet Orante to Violet
f!ttiaiiol veak^acid rt llano 1-aeid
96. 97. 98.
In<loleo3-yl aeetie aeiH Indole*3-yl Propanoie aeitf • Indole-3-yi aaliie propanoic acid
65
91
68
« m
70
92
70 m
77,78,79
68
m
65 3,93,94 65
9% m
![Page 37: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/37.jpg)
( M l * X A Contlaacd) 2 5
SI. HO.
Coapocmds Colour N»dii» ••tersnev
99* Srypto pyrrol* iCK)« tarsi ae l o t . T-S ' I ^ g e r g i a o
i02. Mettiyl Bydra^lae t03* Mel^loniae 104. Methionine solfoxtdo 105. 5-^tliyl boMO (-t)
QQlnolii}«
106. Mothylurea
itbanol-HOl Pale Porple * ? lo lot •• Tollow Boddish Etbaiiol^eci Tollov orange • Telloir folueae-acld
BgSO^
95 68
70 96 68
II
Pale porple or preotpltate
Tellow
Etbanolvtoleusne A d d
f o l o e i t e - a c i d Orange Tellow Ethanol-toloeBe-acld "
107. 6-Metliyl t iydrouraol l
108. 5-fletliyl tryptaaiae 109. 7*Metliyl tryptaaiue 110. -Methyl tryptanina 111. 5-Metttoxy trytaalne 112. Methyl serglde 113. HI Ik and aalao aqgara 11%. ffadrihoa 115. Methyl reaorelaol 116. 5»llethoxy dlnethyl
tryptaaliie 117. ileathol
Tellow i^tolet Violet
Bed
Fink Violet
Oraage to •iolet
Ethanol'-BCl
Ethanol-tlCl
69 70 70
Chlrofona-HOOOB ttbanol-BCl BCl
Ethanol*fiCl
Ctbaaol'-aeid
97 90 98 70
65 118. XeroaptOB
![Page 38: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/38.jpg)
(fi1>le I A Contlfioed)
f t do
SI. Ho.
Coffipounds (^Idttf Hediui B«f«reiic»i
li9« Heprobasiite 120. Methyl ©ttsyl glyoxtme
121. Hiootlolo ftoiS bydrazi^B
122. Norvalaaine
123. p-Nitro«oplJeiK>l 124. Kew Qaoierit^ in Urioe 125. o<l-Kapbtliol 126. -^phtbol 127. l-Kaptitliyl8sloe*3-
SQlpbOQle 60i<3
sulpboole iioKI
sulphonle acid
128.
129.
150. Hapittfior«forcliiol
151. p*i(ltreb«asole aeld bydraxl^a
133. Ornithine 133* Ootadecyeaatloe
134. Pleolloe aeld bydraxlde
135. •iilienylaerloe 136. Proline 137. Plperdlne
Qed aiei} arovn violet
Bed to ptak flurescence Pale orf%t>ge
ma Green
violet Orange to light yellow
Uenzeiae-CCl CCOM nci
nci EtbanoUBCl Ctbanol-OgSOj Ethanol-H^SO^
CfijCOOH
TeXlow to Green Red to piok flnoroaeenoe Pale Orange Dark aaiber pnrple fled to pink flnoresoeaee Pale Purple Bright Orange Reddlah Orange HUiAv
HCl
Ethanol-HCl
99
3
77,78^79
6S 81
too 71
a
92
81
77,78,79
68
Toluene»aoid ** Ethanol Toloene-aold *
BCl Ethanol-RCl
IT
Tolnene-aeld
77,78,79 68
68 Ethanol-toliiene-aold *
![Page 39: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/39.jpg)
2 7
(Tttfele I A Contisuea)
h •'"'»'"
Colour SI. so#
CornxmatOiB Medina Hefereooe
±38, Prildin©
159* rtienylalaeine PyriCo&tm «
l^ t , PJaoaylorea »
142. Psi loc^lQ m i o o t o Pyrrol©
0
m
thS* t%#i>ol8 Of tiigUer !iiol«cular weight and ihosf Gonialning aor« than one OH groop 0-pb©nyl Phenol
147. 2-Propanol
t%8. Polyanldes
149. Perftmes and essential o i l
150. Vhmyl hfAraxim hydlroebloride
151. pliloro«liiciiiol
158. Perptio1»iliB«ieB
153. Qniaidine hydroebloriae
lig^t purple
pale Orange fellow «
Orsisge Oraoge Tellow
? l o l e t
m6 to f i o l e t i»
tellow to
Telloir or Orange
rink reauieh • i o l e t
End ooloar
ma
Tolueae»aoi<3 Etiianol-nci
63
68
ntUanol-tolueoc-acid Toliicnc-ooid ^ L^iio0ol-toiaoae-aoi(3 » Ctfeacol-BCl
n
E!tbQQol aoid f-t&fiaol-HCl Etftaaol-Bg^^
Methaaol-HCl
Red to v i o l e t
Yellow
ffCl 1101
Aoldic eth&nol
TolQeQe->acid
70
3,93 65 71
lot
102
103
10%
81
81,105
106
68 purple tttaaD0l*t0luene««tci4 *
![Page 40: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/40.jpg)
2 3
( m i e I A Continued)
Si* No.
T Colour HeaitSR liefercnce
15^. Cwinoliae n
155. ^ololu© «
156* lleeorolnoi 157« ' esi Qetfbazlae
i5S« Saroosioe
159. S^atole
160* Serine 161• Salphodlazlne 162* Stilpliaaollc aciS 163* Suntooln 164* Sugars «zta.frcMi
corn |i Ian tit 165* fearine 166. 'mrtoalne 167. Tyrosine 168. Ttyptoltonn
«
169. Tryptaartne 170. t r ulB
Yellow n
/u^er CfsasJleU Ueop Bed m4 to flQOrCSOCDCO Pale purpl© m& to v i o l e t
Toluone-Qcltl 68 rttianol-toluooo-acia " Toltiene-eold 6S Ct!iaiiol«tolue»@>oeld " HCl 9S
Ctbanol-HCl
ni^anol vmU oelia
pQle Oraoge ctJienol-OCl
Qltte
Pale Omme Orange Pale Orai|is« Orange solution or blue ppt* Violet
rtltanol-lIOl
«
Hftd to Violet Violet Oratifte to Violet
CHjCOOfl Etbanol weak sola !?ttianol->aci
77,70,79 68
3,93
68
90 B
71
107 66
68 «
108
3,93
70 65
![Page 41: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/41.jpg)
2 9 ( fabU I A ContliittRd)
S i . Ho.
t ' • •• • Coa|>ounds
> Colotir
•
liefUuB ' T ••• •• ' "
il^ference
171. Terpln bydrate icd blood Etbanol-LIGSOJ^ 71
172. ItlJOTOl •
173» ^ttib&Thitawto acia 109,110 174. Urliiiae Ugtit Ijolneiio-ooid m
175. Prea £tbaQol*liCl 09
176. o n 111
17(5. tJrea fonaoKJc^yae restn Bloe Aoetio mi^yanQB" OFIJCOON 112
177. Drldo o d d fe l low 109
178. oc- lre ldopropsuolo sold Yellow to l^ioli i:tliaaol ac i 69
179. Cra^Bll Yellow EtUaool-OCl 69
180. 5~rri t l t lonrael l yellow n 69 181. fi -Pr?lflolsotoutrlo aolrt yellow «
182. -(nmldoprofttaolc aeld yellow rthanol-HCl •
183. Vrtllnr Pale Grange «r 6 8
184. Itiiithifl# Farjple eolour die»tp>ted hy agl ia t ioo
TolneDe-aoia m
185. Ghrcmltm (V) Deep 111
186. Col>alt(tI) —
187. n«3Ui eyaoferrat* ti>ii(Ill) peep mae red Cono.n^sD^
188. VaMdim (V) Blood Bed 8^90^
il%
113
![Page 42: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/42.jpg)
TABLE I B * O«tectioti Ifi naslc Ovl
Bl, Ho*
COffipOUOdS Colour Median Ecferetic©
Aalliae to Oi^age
3 . Beaasoic aolfl bydraside
(Cycloiiwlaffiio©)-te t ra f luro -
benzene sttlfomtniSo
5» 0»DIAII48IAIOE
6 . ^•(©tliyleairoisyl)
sulfooaaidle
Blue to in
Oi^i^o to Violet
Yelloi^
8 .
to.
11.
(etiiy l e o l f o ^ l ) beoe^ene sulfonaigiide
' i - (©tbylthlo) naphthalene stilfooassida
Isosioot lae mcid hydra
Indole
ne tby Ig u 1 f «ny 1) n&pti tha 1 u 1 tomt" tilde
12.
13.
H . p*iiltropli«tiyl iiydmsdoe
Nlootinic acid iiydmzlde
K«|>tliftlon««l/-•u IfOllMld*
Blue to Green i » uv Yellow to Orattge
rellow
81tie to green l o av
Tel low
Ormge to red
Cttiaool-Escn
Etlaa»ol«KaOH
Amoola
CtbQttol-fSaCIl
100
115
77.79,79
115
Isopropy 1 a I cc^o l - 116 lam
CtJianol-KoOn 115
Ftfi»aoi-NaOH
77,78,79
100
Ettiaool KaOB
leoprotiyl
115
77,78,79
115
117
![Page 43: ABSTRACT - ir.amu.ac.inir.amu.ac.in/334/1/T 2133.pdf · «oi«l doa no met t irit freh ... the reactio onf p*DA iritBb anim salti Sinc* orange coapotiae ... 5* Saireki,g* *^otoaatri9](https://reader031.vdocument.in/reader031/viewer/2022022807/5ce802d488c993915f8db1ad/html5/thumbnails/43.jpg)
(TMibU X B Coatiniwd) 3 i
T T su NO.
Ccmpotindl* Colour nmAium Itefcrcnc*
i»»nltroli«asolo aeld tiydrssi(l«
4-ch loroplienyl)->-hyOroxjr tsodolluo
17* Orielnol
te* Piooiii»« a d d h|rdrasEide %»Pti»«roiiyl 2,3,5 6*tetraflaoro-1)«]isen0 sulfonffisidtt
SO* Eisoroiool
Bliw to grem lo uv
Tellow To Ilow to Orango 81ti« to green in trr
ITellov To Hon to Orav^e
31, p-Toluene Solfonanide Tellow 22, |>*(tetr«b3rdro*2H.t,
beaxeae snlfoaoMido dloxido »
ibmoalo
ithaaol-KaOH
Asaoala
77.78,79
115
100
77,78,79
115
100
115
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TABLE I C - Detection i » Heutral Meaitan
T I Colour 81.
SO. CcMspounds Medina llet«reaee
I .
2,
Ani Hum
AnlUoe sulphate
Vellot; t o Orai^e
t o Oraniie
3 .
5 .
6. 7 . 8.
9 . 10. 11 •
12. 13.
15.
l*^iBlnO3iittirai|t]li20i3e
^-JUBtltao-l^S-KaphtHocinlEioiio *
Aroasatlc Sulpbonlo
Anllloo Yellow
Benzylc^no
Boiizldiliie
Baitilttirlc QOltdl
Capsttlos vltli group
C.X.Acld Teilo^ 11
CSirysoldlne G
Plp!ieityl«nl ]ln<i
2t4«-raiilrootiloro lienzeQf!
16. n-«el( !
17. id ton blfiok Hi
IS. l*Nai^tliyl«Mlue
19. I-Hnptitliyl B « l n « - > •filphonlo aeld
T«lloir eta In
Yellow f lack
Yello« stain Tellow to Orange
Ettzer
CHjCCOIJo
EiS»©r
Yello« to oreage
Oralis© to re a
ir«llow
Yellow stnlu
Yellow stain
Yellow to Orange
rt£iattol
Beiizene*a looho 1
ether n
frtfiaool
Eenz«ae*alcoho1 •r
Ettier
Benzene
Benzene-a lootiol
Ether
3, 66,67
11
Yellow f lack Benzene
73
. 3
<S7 n
118
119
3 n
3,6(>,67
3.120, 121,122
92
3
3,66,67
92
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(fal»l« I C €k}iiti»tted) 3 3
SI . NO,
Cfmpowaas Colour Medina Beferenee
20. 2-HapIttl3lyl-6-aslno suliiboEilc acid
SI. 2-SapiiilJyl->6-^i solpbonic acid
Tellow tiooM OenKene
Oxalates or cborides o f Qtd K, lea®
23. p-ph«iiyl©oe dicBalne
2k» o-phciiyleQe diatsine
25, Primary end secondary omines
Sudon 27. Tryptopban 28. llro-re»in
2 9 . Victoria Violet
30. ftex ' oicfeel
rellow to
follow etaii) Blue
fled to ITellow
Ether
Do s i l i ca go l ctsoofsed by boazyl cbloride vapours OetizeQca lc<^ol OoditBQ nitrate r.tbffiQOl Beazeoe sulpbonio acid-Kaon
92
t06,123F
3T66,67
10
3 i8 , i28
2
127
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3 4 RRrfcRKKC h S
EbrliofofP., Mt^ioln Wocbe, 19OI, 131. 2* Tejdelak and Xakac, Fa*t»re&ktiomtJ io dcr apektropbottmeterlsdtiem
Amtyse Of^atilscb© ?erblndmigtfn« 1969. ^ 179# 3« FelgltP.y *Spot Tests in Oiganlo onsXysis't Seventb r^ition,
Elssrier Pii^liiAiqg Company, Unadm, i966»
StrGoll,C*A.» and Aoalrtioal Ci^eesietiy of Httroieii and i t s eonpiiaiia** I^rt I a Port St lotcrscieoce, loaam, i970*
5. aoa ^ e l l f C . A . , •Colortmetrio Method & aiialysist Vm ^ostratid Princeton*, i959» i iA, 793* SawiciEi,E., *PtiQtmGtoric Onganio analysis** Fart 1, Viley intsrsoi^osf Losdont 1970*
7 , Alesaodieryn.S.t nndt OutlertA.O.t «}.€tics:«S€ND«per^lo Tx^nsaotSons IX, 1976, 696.
8 , OhaarifS., Ogata,H., liteda,^., Kirs,S., Anal.cascB., i972, 9 , Dstta Gapta,J.K,, and Saba,M*n., Acta Crystalliirapttica,
1973, 29(6). i228» iO* 1Costyul£ovakii,1fa.U, and Xsobert,0., Pro» Obraztoy Tovamyl Znaki,
1973, 50(13). 12^; C.A.1973, ISLt 3833* f . 11, T«saasil,s., Xiidi,N.Maiilcaiio,T., and 9biho,p«, Yakagalcuzasstii,
<973, 93(5). 65*; C.il.l973, 22» 38315 a . 12. i«baflnn,J., laneat., 19*6, 1*; C.A.19*6, *0, 73004.
t3 . K:iyns,v,, and Nanbouse.J.r., Ibid . , 19*8, 252, 611; C.A.19*9,
*2. 5**0 li.
1%. BariUi .V. , Biol .soe . i tal . i l io l tpar . , 19*9* 25, *; C.A.1950,
W , 9501 d .
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f 1
29(7). l%38j C.A.t97%, 81, 1%5%52 1. 17* iliini«jrt^*E«, Baiir«sr«S*S.t emA il.Oireaiatogr*,
19fi9f %5(t)» 82} O.A.1970, 72^318655 » . 18. Spi«s»«l.!l., and QiaaibcrstD^C., Aiial*<3b«Mi«, 19%9* 21* t9* MtiU»rtS*B. and HoQerlag«»»n.» Daitt.ApotticlceiwEtg«, I960, tOO. 509;
C.A.1960, 16750 20. Sswlek^E., Stanley, f.V*, and fl1>«rt,V*C.» Anal.aia«*, 1961, 21* Sa«rie&l,E*, and ^otiaeoii,B., Ctiamlat-Aiialsrst, 1966, ^ 101« 22. Sawietcl,E., Pfatt,J.O«, CbiNBlat^Analyat, 1966, 6. 23* Cesal,C., and Seraflnl-Canl ,r. , Bloehea*J», 1965, 88, 152. 2%. St)ftirt,E.K., J.l%aar».Sol., 1975, 62(9>. 1550. 25« Sor«naaitii,I*ll« and f}orokltOT,A.A., Tr.Sbla.Taetinol, 1969* ^t 155; C.A
1970* 75, 49059 26* Srp«r,L. and lfagner,E., Masertatlon Ptiara., 196%» 16, 555s C.A*
1965* 62 ii65% C. 27. Xttpfer,0., and Bri«g««an,L.L., Anal.Sloebaa., 1966, 502. 28. fhmm Sim «ilnii.Ding Baidi mol (TlatHaa) lliv.l!ad«(Baaol), 1976,
136; C.A. 1978, 79153 a. 29. llllott,Roibat,J; Gardttar,Bagold.L. (Inat .Pathol•QiMaii*a ttalv.
Balfaat N-Xra) Bloeliaa.Blopfiiya.Aota., 1977, 498(2). 549; C.A. 1977, S b ^911 1i.
30. Salyam,G.S., Padotm,L j i . , 1969* 20%; C.A. 1971, 22t» C* 31. Bi«al,T., Bokkaldorltao Blaal lanyttakalio, 1969, l^, l l l f C.A.
1970, 72-3. 3966 2d.
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32. and Btiaseit ,r*fPl iaranzlet 1973t 2S(9)» 611;
197%, 7018
33* irattg,G«V, and €airisp,J.D.» Anal.G&ea*, 1952* S00(>» 34. ®iln,Ki«v.(J.SS.».0»Sr.iabl» m*{nuB»tm Etd.) 19?%,
40(111, 1207; C.A.1975, 82, 14890% 35« S«le8,*I.E., imal.dtoB., 1950, 36. Upina,t.G. (iQst.Glf.Tr.rrofsabol^Gom U.S3.B,) Gls .tr .Prof .
gaUol., 1970, 14(12), 50j C.A.1971, ^45953 f .
37. lJlpln»,T.a. (XQ»t.Gl^«fr.rrGf8;«bol.Gor^l O.SS.S.) Olg.fr.Prof.SaDol. 1973» i , 45t 1973t 78, 101565 a .
Pir2es@yolc^l,Jlati*Blllbauer,st«fanla. ( Lob .Anal .Oois.Zdfisw.Batlfyv. EatOKlce Pol.) Olago.lalj., 1976, 18(4>. 225| C.A.1977, 8i§, 1S83 c .
y^m and fr.PrcB^or^.Xast., 1969, 97i
C.A., 1972, 2I» 115580 ©.
40. Ol}tesparaQskaya,S*t.i and Zlol)ln«f7«E.¥eatn leost umiv.iiiia., 1974, 15(2), 247} C.A.1974, 81, 72321 a .
41. Kaget2]i9i,M,M[.CAktma»T., anH HoriK>retT.J., C3>e».Ff3ara.5all., 1971,
mm* 2294. 42. IClvirllEbo,s:.I. and M.Lle Sata, ScatMl.LMl., Clln.Lab.Invaafe, 1959,
U^ 128| A.A.I960, X, 4427. 43. Prolq>.n.«}«, and l3d«nfrl«nd,S.» Aoal.Blootiaa., I960, 228. 44. !falc«nlslil,Ai, (Fae.Phani.tliilKl.milT.llii^aiAilaflialca,Japan), Eisel .
Haga&u, 1978, 24(1), 25; C.A.1978, 8^, 80^4 w.
45. X8«all.A.S,Tasaa,D.A., and Aftla,B.A.,Ptianiasl«, 1974, 29(5). 348; C.A.1974, 81, 82440 c .
46. Da Readar P.UAnal.Ctilm.Aota., 1954, 11 68. 47. Norris,C.«r.G.Bloohi«.J., 1941, 952.
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f . n
48. la Rosa.fe.V., .J.lab.Cllo.l ied.WS. 30, 55t} C.A.19^5, ^ Iatieet.1959* jU C.A.1939t 33, 4620.^
50, MawcmiyC.A.t fiioohe««il,» 1942, ^ 845. 5tm Felblg^A*, Jaiiie!riyS«t Stoo8tl»»E», Acta Fol.iniaiiii.,
1971, 28(t)> 19J C.A.1971f 2 i , c . 52. CottUeh.S.ll.OsiiisIc IliSa.rars., 1950, ^ 40; C.A.1950, 4632 g . 53* Hoife,«I.W., Tasanura,ir., and B.f:.Clork, Coreal Oiesi., 1972, 49(5^.
566; C.A.1972, 72^ 138^3 l». «itt ,G.V. anil carl«p,tI.D., Anal.CSieei., 1954, 452.
55. Prescalua,y., Fre8enlti8,E., ScSiiiol<ler,b., (rieslia^aa.Qer.) Knus.Tech, Diseo.Vortragaveroeff, 1972, 59; C.A*1973, 7659 r .
56. Mtllis@,J.C. ati«l sialics, [UB., Aaal.OiQm., 1956, ^ 846. 57. Drowfi,B., Anal.Oaeei., 1958, 1844. 5 8 . S o o i i , F . L . , PgosoSe Bwaha, 197 », t 2 ( i > . 3 S , €.A.1975, 8 2 , 5 8 6 2 5 0 .
59» «orln,l».0. , and Pros ,J . N . , 10 OGC.1974, 3 , 8 5 3 , 4 7 3 ( c l . 2 3 » 2 3 0 0 .
Coin)? C.A.1975, 82, I»701l5 U.
60. BarreiisGtiaeiifd.l,, Bioolie».Z., 1923, 140. 426. 6 1 . Soi)ttls,R.Ar^.Aclcar-pf|}laiiz«id>aa Boalenlcd, 1 9 7 5 , 1 9 ( 6 ) . 3 9 7 .
62. Vfttaon,C.J., and BaviclQ8on,V., A».J.€llo.Pat.&., 1947, l^ , 108; c .A. 1 9 4 7 , 1 1 , 3 i 6 1 o .
63* 1964 Book of ASiaf Stanaards, Part 20, "Paint Varnlab, iacquer and Btlated Pro^tsota*, Awarlonn Soelaty for taatlng and aateriala, ptiila«alplila, 1 9 6 4 , daalgnatlon D . 1 9 2 7 , P . 7 8 1 .
64. Siiann,M.H., and Adaw8,M.L., Of f i ce .Pig .rederat Ion Palut.Varn.prod.
el .1959, 21, 1247, A.A. , I960, I , 8856.
65. FUlg .C.Bul l .Soc .Qi ia . , 1908, 2t 1038; C.A. 1908,
66. CbakraTartl,S.N., and noy,lt.B., Analyst, 1937, 603.
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8 8
67* S«lcai»S«» and Coworkers, Japan Aiialy«t, I960, 862; C.A.1961» 196166 b .
68* Anal.Cties*, 1956t ^ 1321. 69* Clt&etQ.HegautheyyC** and Aoal.Cliai*,
1956, 28, 70* Alli»tim,G,V«, I}artlotttA«F.F«» Be Fa^ert and
1971, 23ii)m 72f 1971, 85811 r , 1971, 555j C.Aa971» 2S» 9522^ « .
71- 1929t 66, lOlj C.A.1929, 1717. 72 • Kra&owica, Povo I , Izdeb* SHa-^&osa • Susaana • (Inot r ue l i o r , trarsa^ •
Pol . ) 6raslioa«C3ii>robF.Ploo., 1970, 38(12), 1 1 ^ (Pol); C.A.1971, 1081 n.
73. PlrlcM* 15 Ai^.'1973, 130, 017 (cl.Co7d>; C.A.197%, 80, 78199 t . 7^. RaicheltjD. end Gcbtfarg;e,n.ZcntroiblG Plions.Ptiaraa Kotiier Lob*
Orotorisdlstif 1972, u i (^>378; C.A. 1972, 77 , 6816% u. 75. mtorocbeale, 193^» l i t If C.a.1934, 28, 6 ^ 5 ! 76. forgftr,^. and lfaller,J«pratrt,(3)«ii*, 1968, 2£t 371. 77. Pea«z,M. and Petlt.A.Bnll.Soo.Ctiim.Flrance, 19^7, 122; C.A.19^7,
5820 1. 78* P«lff.l,r« ana Maniiliaiaer,%*A.MikrooIieiile Ver«Mi&rootiia.,
1953. fW. 355,
79* P«l£l ,P. , 'Speci f ic , Sel#otlvtt and S«n9lilv« fieaotlons*, Acadaislc Press, Htw York, I949t 530.
80. 6olyanlt8kll,D«X. ana reregudova,T.A.Vop.CH[)sliotis.Kl3l8i.Blotitilii, 1970, 152; C.A»1972, 30%17 C.
81. Anger, V. and Ofrl.H.Z.Anal.Ci>««*, 196%, 203. %25* 82. Qureshl,H«, Qu]restil,8.Z. and Slngtial,S.C., Anal*C3ila.Acta,
1971, 2X, 361.
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3 9
S3. Qitr«Blii,ll., and Qiir««lil,S«S.» Anrnl.&kmmt 1966, 2SL*
Bhm lad^ryL.D*, Statle,II.J»t and KliBifoebtiisetiart 1970, 18121, 191.
85* rclgl,P.Aaser.V.» and 9Sapp«rt*ll«Mlkroeft«ile, 193%, 16, 1935, 80®.
66. rrledl««iia«r,p«, 'forisehiilttetSair feofartieMfattrl Katloa, 1891, 2, 79, 1896, 2*
87* Kiirrer,r.Organic ebcalstry, %tli [email protected]«r, Aant«rd«a, 1950, i)-63*.
88. l lestr,L.F» arnO nc8er,IB«, Orgaelc ehtalstry, 2nc! Cfd.Qealidibld, Kew York, 1950, |>->905.
89. Stilta,n. Kainrvlsaens^afieii, 1932, 622.
90. Sch«all,N., aad Hawrylyirtijni,!!., Aoal.Cliaai.,
22^ 1139. 91. Gupta,n. and Bll>tiiitl,n., Anai.C9ieii., 1970, %2(6K 659. 92. r e l s l , P . , and Halnl^ergar,!.., Mltcroohla.Aota., 1955, 112. 93. Flsctier,!!. and Pbyslol.CbMi*, 1911, ^52.
9%. SallEow8kl,E., Bloctictt.Z., 1919, 2It 95. XmQe,D«G., l(lra«blta,f!.,aBd lfaj«r,^.R., Natiira,
22% (5221). 811. 96. llekaisila,H., and Tard.A.^t., Anal.Cli«ii«, I960, ^ 195%.
97. Kiniar,S., and llaaaan,P.ff., r.J.Agr.Pood.ClieB,, 1972, 20(61. 11%1$
C.A.1973, 2£* V. 98. Aeli«aon,?i.M., and Tttrn«r,X.J., CbrcMiatag., 1962, 520.
99. AiitaiteaM,H.O., a.pliara., 197*, 307(11). 887.
100. Barada,f., and lllkinil,K., J.Agr.ChfM.Soc.ilaiian, 1950, £2, %15s C.A.
*5, 10578 t .
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4 0
tot. Asal>«,T,, KtaMt«,K., Saziijci»fi. end T«i&itani,S., Stmsekl Xiagttou»
1975, 2%(3), tfiOj C.A.1979, 82» f . 102. Autertioff.H.O. ana Bauer^n*, Apoth.Ztg,^ 1969, I09(%<». 1523;C.A,
1970, 72-73. 5^706 x . 103. Placsieic,!., Sonatstoffe, 1960, ^ 17%. 104. MollcrtA. at3« ScifeD Fctto.O., f.acUse, 1974, 100(12). 289j C.A.
197^, Bit 1113S5 w. t03. ana Jwiisrels,-.*
1963, 12, 113. 106. tiOOt<m,l.D.P., •fttcroaoolysls in Medical Dioctjcislstiy, C^oi^lillly
Uvimi&tom* r^loburrli, 197^, p-e75.
107. AbroffiovloUfO.Ya aaii t o tar ,^ . ! . , B!lcf£Oljlol.,
^972, 8 (4) . 509; 2£* 108. Froliden,©., ona Gol5f:ctiaidt,l-., Ml&rociil® Acta, 1937, 351;C.A.
1937, J l , 8824. 109. F0i«4l,r. anrt Ilber; ,ott ,n. , 19^4, J6, 132. 110. . am PlaiS8nce,C., J.AJScr.Soc., 1916, 303. 2156. 111. cUae^n.r. and Aiml.cascsi., 1936, 47. 112. Sitantt,M.!f. and rs}>o0lto»G.0., Anal.CiJp®., 1958, 107• 113. JoharyG.S'.., Mlluroottes hotBp 1975, 61$ C.A.1975, 82, 67693q. 114. Cfgimm^i-'** Morafel«c,Csso» I©cft., 1971, hS, 115. Braa»fi«w,^.%., i l . d u - ^ t i i g . , 1969, 49(2). 422. 116. va«l©ljy,H. aof! r]rf>tidet),0., Mlferoclil«.Aota, 1937, 55. 117. Felgl.F., 4nier«V. and Miferochlw.Actft, 1962, 878. 118. Conrad,N. and Bar, 1901, 1685# 119. J&>m!o,T. 01 Nay 1975, 7549, 170 (ol .n 01 j.CllB.B41M.Ai?lfe}; C..%
1975, 83, 1486044.
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4 1
9idtlitP«J« and JonesyE.* Aselieae of QiMillt«tiv« AtMilysiSt JUmaon, 1953, n o .
121. Staff of Bopklna and IfiUlaas Researob taboratonr* 'Organle Baagfnt for Oisanio analyalsS Brooiilya, I W * 50.
122. Kirrer,e.P. and BallartlC.t Bolv.Ghla.Aeta* 193S» ^ 463. 123. Claw.E.Bar, 1894, 12, 2938. t2k» Noor,F.J« and Gal«»H«D.« tl.Aaer.Oiea.Soo., i963» ^ 399* 125* Hux^yS.* irttefsaim^J., ana Erle»aimtG.» Ber« 1959, ^ 1201, S26. RaiTi»oa,t>.ft«9 and ttofBasn,T.» BiocliMi.«f.» 1961 • 80, 38 pm
127. FolglfF., Anal.Oiai., 1961, 128. Hour El-Ma, Raaami,H« Hield.M.Y. and fU^elth El-Sayed«P.A*,
Bull rso.^8ni.Calro*tltilv,1971, 10( lh 61. 129* Ookunibtilntll.S. and Salova,{l«A«, ^.Oii .Sli l**, 1974, 10(12). 2610. 130. Tarlv,S., Israel 1964» 2, 29f C.A. 196%, ^ IIP. 131 • Wartjmov.S.v., Obraztsy.fovamye.znakt, 1972, 49(30). 204} C.A.
W 3 , 2IU 58003 132. ralgl,F. and Stark-Mayer, C.Cbenlet.-Analyat, 1957, 37. 135* Qartat»l,M., Qaraslil^S.E., flatliore,U.S.,and All MoliaMmd,
J.1>ltya.Ctie«., 1975, 134. Boae,F.K., Analyst, 1931, 504. 135. velnaeHenk.A., Bar, 1901, 24, 1685. 136. faoliiidl-Stelner,!., and Tranew.G.Piiani.Aota.BelT., 1963, 846t
C.A .1964, 7874 f . 137* Uvlne,J.N., and Stelftwiian,F., CUn Cbea., 1961,
C.A.1962, 56, 3759 f . 138. Boyera.A.F.M., and Taa.N.M., Clln.Oila.Aota, 1964, 197. 139* Salk»iraiiy,S., BloehM.2., 1920, lO^, 185.
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4 o
1%0* Aa«cr»V«* and ]flferoctil«.AoU., i960, 592* U l . rro<3«U,M.K., and €bttigiil;»V.X.itlci.likiv.sli.l972» 58(10) 10%5$
C*A. 1973, 78, 29702 i%2. Pbsm.flft.lSierK 1972» g7(5K i%3« FiatnOfS*, and Htrozava»Y. {Cl.X)ci69,C09^), i7 Juna, 1972; C.A.
t975, 21* BannoVtS.N*, Bliitat'«B*£l*, and Reakts.Sporobnost.
Ors.sodiii*t WO* 7(1 h 1970t 22» ^5672 x . Qiireitil,M*, fiatl)ora,fi.S.tflBd All Mtibamd, Talanta, 1976, ^ 87%.
146* ana Moiiaittt*T,j«, Stoeiies.^*, 1933* ^ 192%« i%7* I«OBara,R.«l*, and PatdrataUa»4*ir., J.Org.Cbeai*, 1963> ^ 3021* 148« Kiilia,!}., and Lair,J,, Bar., i939f ^ i457* tk9m Paaas,ll«, and Biirtln,a«P«, BoU.SoQ.Cbia.soo., 19^9, 1996; C.A.
1961, 445 150* Saiitti,F.a« and J o n e s , A acheee of Qualitative Analyala, London,
1953, 110. 151. 0aipettko,P«0«, and Tii^obettko,2«6«, <!.Gen.CbeM«(U«S.S«R.) 1941,
213; C.Aa941, 79*9*. 152. Bidlo.]e.Vodni.Bo.iK»daaatiYi, 1966, I6(7>. 292; C.A.1967* 669
14077 a. /
153* OafinanG.V. and Selirainr.K., a.Biol.Cfeas., 1954, 695. 154. Otikom Saiioiii, J.Pbara.Soo.Japan, 1955, J h C.A.1956,
115 H. 155. Barry,B.K., Saitoa,B.e., L.Ciiiii., and Ban7,J.S., Oalv.Tazaa,
1951, 22, Piib.llo.5109; C.A.i951, ^ 10291 i .
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4 3
G 11 A p T g n » m
COHnfNSATIOS oy p-IUMFTimj IKOB HEMDaifKE httn hMUm. Wi milWMTF.
Our e a r l i e r work eliows ttinf p-dlfsethylaiitfii^eitssol^shyde
i s an iaporimit aoa ly t i oa l reagent used f o r the Heteotion 1 2
and detersiekatioti o f atimerous orgaaie compowds rew eoxuSensation
products of ih-mQ with oidnea tiave f>ecQ studied * • IBieir i s o l a t i o n
has beea fotmS t o b e d i f f i c u l t aM the i r i d e a t l f i c a t i o a lias been smac n ^
i n 0 cursory ssaoaer** • Infaot i t i s d i f f i e a l t to prepare Sch i f f
base trm reaotioa witb aaiiiie s a l t s o r aisiites in a c i d i o medico
beoatxae tt^e Belliff base forced tongs t o reaot fartber ftiving
protonated Sobi f f base. Tbc co lour o f the ^ b i f f base i s d i f f e r e n t
tban tbat of ^ e protonated ^sb i f f base* Purtber tbe co lour o f a
crude prodaot i s occasional ly d i f f e r e n t
fs^® tbat o f the c rys ta l l i z ed
oa©» As a resu l t soate o f the e a r l i e r ri^arlta^ on l^ie p-&%B<-omine8
co l our reaction seen to be ao«l»tful and adisleadifl^* fbere fore an
atteispt has been Bade to i s o l a t e and identiji^ tbe p-IMB-aniline
percb lomte pit^dnot tbat i s tbe siasplest one and t o compare ^ e
resul ts <A»taiited witb tbe reported observations o f the co lour
react imis.
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44 B X y E R l l l E i l f A L
a»Mtnt«t il»«feitt« QMd asialytio*!
ik^VBvmtmt r«rlet»-Elmr 621 imd A GO D Vftrtfto •iwetrO|)hoto««t«r» and ii i i l lp« x»ni9r mi% viili <iiffraeto«tti*r ir«r« for i . r * , a.a.r* ftiMl •tQdi«9 r*s|>«etlvcly*
laolattott of prctiloratg Schtff Hie protonated Seliiff tittM wntmimt^A with i>«rf^lorie aold (^STO) ean b* by adding 0.02 sole (2.98 Of to 0.01 sola <i*93 gas) attilina pax^lorata to 29 al of atliaiiol. On lAiaking tttoroogbly aftar aaeb addition a yallov product praoipitataot avp.
Ilia protoaatad Sobiff baaa» • M-FbCiO^ (PSB) oaa ba obtained by diaaolviag VSBC in bot atbanol* on oooling r«d aaadiaa aaparata* a«p« 23%*C.
Pataetioa of obtoriaat ma praaanoa o f i^lorina waa dataotad by IaaaaigBa*a taat*
X»ray atwdiaa« l«ray atndiaa ware parfonad by powdar aatbod witb aiokal filtarad Cal^oCradiatioaa*
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4 5
R e S C L T 8 A n U P i S C t T S S I O H
CoQdeasation of p-ElB witti aniline perc^loraie gives on oiiBii^e product, protomtea sc^i f f base oontamiiiated perclilorio acl^ (Pf>BC} end a red prodiaci* protonated ^ h i f f t^ase,
« Kl-PbClOj <PSD).
f^r Psnc percentage of Cl i s bigber tban repaired (tables 11 end I I I ) * Presnmabl;^ PSDC i s centesinated viUi pereblerio aoid and tbat 4nst possible due to tertiaxy mine group in Doth p ^ c ond pm gave tbe saaie d vala^i by poiider metbod of x^my analysis, i «r« speoira by SBr nottioi and n.n.r* spectra in triflt»>f^oetio aoid. aowever, tbe speotro for Pi^ are veiy i^orp ond liioy are not so f o r PSBC# Hie x-ray data for protonated Scbiff base (PSB), p-0M3 and aniline percblorate are r.lveo in tables IV, V and ITI. ^ e s e data indicate tbat pm i s a mv cxystalline ooiipotind* Ibe i * r . speotra showed fonr bands at 1635(iry, i600(VS), iS79(s) and in tbe regimi ilKK) to 1700 cm"*. Probably ttie very strciig infra red absorption band at 1600 om"^ i s indicative of } c • • ^ e n.B.r« spectra consisted of signals ocourrim;; at 3*58 (S,(S1), 7«78 (S,5n), Sm 8.08 (J • 6ns,d,3l } , » 8.61 (J • aiEfd,^!) and 6 « 9*28 (broad peak, i l l ) , on 60 ^ s Var ian . f b e s i g n a l a t ^ • 9*28
i s indicative of -Ca • H < •
Feigl oienticmed^ a test f o r prismry and secondary aitiines witb p-DAB. Ibese amines an^ their salts <K>ndense witb p-dintetbyl* aainobenzaldehyde to yield coloored Sebiff bases (Scbeiii*-5)«
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59
f>4 K)
X o
X o o f fNj
X z
O X + (M rO X o
I X o UJ tA
K> < X CD U
«n I
UJ
UJ X O i/>
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4 7
Vltb iii0ii0Antii«« tli« Sobtff t>««* i t ar«llov» «t}«rea« and
polyanints y la ld omnge produota in soffie oasea* Probaliljr »ora tban on*
Nflg ooQdaiiaea i o ttiaaa instaoooa* the fa c t ttaat tb« oo l oor o f
Setiiff baaes l»eeoeaa eora i i iten«lv« b r Hie aot ion o f S i l s t od aoida l e
dtia to tba protonatlOQ o f ttia t o tb« -Sn«CQ» group* fliaae
ooooluaiOEia aoesi t o ba doiAitfiiJl*
Althoogb tb« asperlateatal oondttlona o f the raaotioaa
(vide BtfaS) were d i f f e rent fr<»B tbat oved in tbe preaent paper and
the eo loor o f a erude prodoot i s oooaaionaliy d i f f e r e n t fron tbat
o f tbe oryatai l iaed one tbe fol lowing ooisparatiire oonoltieiona m^y be
drawn•
p«mB does not reset wit^ f r e e aisinea t o g ive tbe Soiiiff baaea.
Xt reaeta^ witb f r e e astinea onljr in tbe presenco o f an ao id . tlEoproto*
nated Sc^i f f baae» yellow compound* cannot be obtained from the
reaotion o f p«OAB w i ^ a»tne aalt* WornvBr^ i t oon be <^tained hy
neutralising the protonated Sebi f f baae» PSB, witb an a l t o l i n e
so lut ion as sodiun bydroxide* Sinee orange ooopounde m»y be tbe
oontaainated protonated Seb i f f bases (PSQC)* red ooapoimd i s a Sebi f f
base (PSB), d i s t ine t i on aaons vono* di and polyanines m y not be Biade
on t b i s b a s i s .
Bensaldebydet einnaaijrldehydet vani l l ine reaot witb an i l ine
o r ani l ine pereblorate siatilarly i*e« as p-OAB resets* Sa l i oy la ld^yde
reaets witb an i l ine t o g ive a yellow Sebi f f base and i t l eaots witb
an i l ine pereblorate to g ive m red protonated Seb i f f base*
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fable IX -> r.lment&t azialjptls results of PSaiC
61
El^seute t ' "'
Potmd i't) Ee^ulrea
C 55.19 55.90 n 5.25 5.20 13 8.59 8.60
CI 10.84 10.70
t^ble III • Ela^ental results of I SB
f!l«9eiit8 ¥ • —
roimci ilGQUiff^
C 55.36 55.50 H 5.31 5.20 n &.m e.60
c i 10.7S 10.70
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62
faDle IV • X^my data for protonoted Scbltf base (PSB) obtalued from p»r>AO ami! aniline perchlorate
- if"" & valtws I / I o
•'4 & vQim* l / l o
l i . l 9 0 1% 3.291 20
9.130 15 3.250 16 7.280 32 3.186 09 7*080 42 3.100 17 5.718 10 3.080 11 9.010 100 2.950 07
13 2.83% 13 22 2.7%% 26 16 2.503 07
^.152 37 2.380 06
%.085 18 2.30% 07 3.825 73 2.235 07 3.700 09 2.090 06 3.561 27 1.971 05 3.53% IS 1.921 06 3.370 09 1.719 05
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T - X-ray data of
5 0
d values I / Io 1 •
d V8ill«8 —-J
l / l o
10.275 13 3.615 53 9*604 16 3.424 36 8.750 89 3.348 40 7.t32 13 3.229 48
15 3^076 98 5.980 18 8-760 16 5.^33 17 2 . 7 ^ 21 5 a 21 98 2.440 16 4.663 72 2.120 11 4.307 100 2.056 11 4.073 21 1.963 12 4.000 17 1.815 08 3.830 65 1 . 6 ^ 08 3.766 95 1.609 07
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5 1
fm%U t t - X-ray data of anilina parotilorate (ASt* Card No,7-508)
a valiits —1
l/lo « ' ' " '"
6 Talact I / I o
7.84 50 2.45 50 k.kk 20 2.40 50
100 2.25 10 60 2.12 10 40 2.04 20 40 1.99 10
3M 50 1.95 10 5.54 40 1*92 50 3.24 50 1.87 5.15 50 1.82 50 5.00 50 1.75 10 2.69 50 1.67 10 2.65 20 1.66 10 2.60 50 1.62 20 2.52 70 •
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5 2
H y P E n r K G I. ;>
i* <ures!)l«!<U, UBiiiOTetlimS,, MoiiamaatA*, Talsniat 19769 874. 2. uatboretl^^M.t aod Htjhammdth^t <I*F!iy8»€33es.,
1975, 2 i . 3. uatlioroffl.8., aafl t^urosbl,?!*, Talonta, 1978, 235.
4 . illcsna«3er»n.r>», otit3 Outler,A«Q#, I I , 1976» 696.
5 . Foir,lfF*t 'f^pot Tost In Owueanio AmlyBie^t 7ttJ L'a» P.2^3, rleovior AiEStcrdaffi, I960.
6. Anal.Oieffl., 1966, J8, 1956.
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5 3
C H A P f f g R ^ I V
ooiotm RgACTioN or jpiHiRNifUMiHE nwt ALmUtms
mi»li«iiyliHiitn« an laporiaiit anslrttoal r«fti«iif* It boa b««ii as«d in mny oxtdation-rtduotion tttratiooa^* It baa alao liaaa taaad aa a oliroKfigaolo reagent in tlia aataotion and tfatarataation of aldehydaa^*^'^, angara'*^, *anad4aa^»® ato. Quwahl® «t a l , hava pt^ItabaiS a aenaittva audi aaJlaotiva raaftii •pet taat for HiptiensrlaBiina* For tbia taat tba Unit of idantifieation nas foimd to be O.S^Ag In a Hotting dilation of s iO^* ftoa teat i « baaed i^on tbe reaotion of dipbenylaoiiiie witb p->aioett3ylavl nobenxa Idliyde i o tbe preaenee of bydrooblorto acid* In tbia reaotion tbey bore noted tbat a yellow oolour ia fonaed «blcb on beating tuma green or blaieb green* fbe ooloored prodoota Obtained fro® tbe reaotion of dipbenylanine with aniara bave been atndied by Moiioae^*^ at el* ^oently^ dipbenylaaine baa been uaad ae a general r ^ e n t f o r tbe apeotropbotosetrio deteradlnation of aronatio aldebydea* Aronatio aldehydes end aove o f their binary nlxturea ean be determined• fbe maximum error «aa found to be • 6 and • iOfI f o r aingle and aiBoltaneoaa deterMinatioa of aldebydea reapeotively. Bowevert tbe iaolation and identifioation of dipbenylaaine aldebydea reaotion prodtieta bave been fotind to be di f f ioQlt and i t baa not been reported eo far .
Wcnr an atteapt ia aade to leolate and identify the eoloored produeta of tbeee reaotiona* ibe reaolta obteined are diaeaaaed in tbia Chapter.
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5 4 B X P B R I W E N T A I *
jtegjyntei llt«g«iit» used if«r» of aiuilytioal cr«d«»
Appratutt Baotofmn 01C»SAT PariciKHEliMr 621» A 60 0 ••rian and A 90 8 varian and V %500 apaetrofitiotoitataraf pltlllpa x*ray imit witti dtffraetonatar f o r a«T«t a«n»r*« and X' ray atndiaa*
Pipaparatioa of fltptitiiyUwloa paittfiloratai f o o%t«iti « •atiimtad aoiuttim of dipbenylaalne «aa pfvparad la attiaaol* fba aolution waa feaatad on watai^atli and tiim eooeentmtad paii^lorio aoid (€0%) waa addad to It* Ilia eoi^entration of parctilorio aoid vaa tvioo that of dipt!anylanlna in ttia abova aoletion* On ooollng* tli« ^rodtiot oirataUteed* f t tma f i i tared and dried* OiitliansriaBiina (>er<^lorate obtainad «aa in tlia forvi of tranaparant evblo orratala
i58*160*0»
Xaolation of olnnaaartoidafayda^'diplianylawina parclilorata produot
< i ) TO S«7 gm (0*01 aola) of dipbaqyiaKlna perohloratt aolntioa in
atbanol (20 ml) in a ooniaal flaali waa addad 26 ml (0.02 sola)
of oinnaayldahydt. On awirliqg oranga oryatala of ai»p* i95*C
vitli tlia avolntioa of liaat* Yha aryatala vara fiUarad, vaaliad
with atbar and raoryttalliaad froa aeatonitrile. fha yield vaa
biiH
(it) To tiia aibow awaat of oianaayldaliyda in iOO al bansaaat vaa
addad half of tlia aliova aaouat of powdarad dipttaoylaaiaa
parohlorata. On thorotigb atirrlnf tba diphtnylaalna parohlorata
diaaolvad iaaadiataly and oraafa aaadla lika arrotala of
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5
t93*C »epQratca with tbo evolution of Heat* 2n tliis prooedtire ethaQolle soltitioa of i}t{^«Q]rla«lne p«rctilorate (5 ml) ooit be used tosteaa of the solid powaer* the yl^M was very tii#i ismy*
Idolation of bePZQldehyae«dl.f?liciqrl8aiitic pgrdhloroto prodHictg
Yelloif protluct: To (0.05 oole) of ftfsazalde&yde in 250 ml of mthon
tetracliloriae m® AFI E %#2 gis mote) of ai^enylnEine, A clear solntloa «ra» obtained t tj 1 cti (^tvea a so f t irellow preeipltaie OQ adding ecmoeatratedl hy&itodiloriG mi& <0«5 s i ) iiropwlse « i tb conttnuous 8ba&l£ig« Ifhe precipltete so ol>ti3l»eS was f l l tcr«at westied ^ItH oaition tetiQc^loriae mad dried at Slei ler yellow*orat3ge pm^doots cm
l»e preolpitotedi for o aaisalae^ydte* salioylaldeliyde ana O^vaiiillliie* Ferolilorlo ooljl or ealplmrio aoid oan ol«o he ttsed In ttie plaoe of tiy^rooblorio ooiS*
Oreen proflyctt f o (0*02 iiole) beossald^yde Is 10 tal etbanol aMed 2«7 S (0*01 nolo) aif^eoylaas^OE perelilorate. h yellow eolutioo tras obtained iriilcl) trnms green on beating (1(K)*C) for baif an bour* After oool io i (0*cy a green gsMniy precipitate trae obtained* Ibe precipitate so obtained waa fi ltered* iiaalied« dried at 30*C and tben diaaolved in aeetonitrile-perebloric aeid ( i s i ) nixifire* Froa this eolation a green prodnet was precipitated by adding water in eaccesa. ftie product vaa filtered* tfaebed witb «ater and etiianol and dried* Similarly the prodncta can be obtained fron the above nentioned aldfhydes-dlpbenylttitne reaeti«m*
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69
P»t»cti<m o f cblortoes pi^seace o f ©lilortii© vas deteote<} try
iassalgiie*»
X-rayt X-ray studies were p«rforsed by po^a^r methoU witu olckei f i l tered CoS raeietlons.
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r'
It E S 0 L T B A IS D P I S C U S t a l O N
Diplieoylanine reacts wltib aldf^yctes in acidic solntioiui, i t s salts (tikydrooliloriaet solpbate ao^ perdilorate) react iritti aldehyden airectljr* tbeae reactions may divided in two classes, flic f i r s t i s basedl on the fomatioo of a very tenmry ieinivst salt as i t is found in tile case of oiommorlclelisrac oc^ i t s tdierivatives*
strtiotore ciiroo in {na r be proposed for tbis prodoct, N-oinnoi^ldeiiedipheiiF^isilaitas percsblorate. following ovideoces are in the support of the strcKiture (E)« preseoco of di lor ioe in corapoona (E) was fotntt! to be positiim. An esplosivc craclciiig on beating (e) indicates the presence of perdilorate group, ^ e acidic solution of (R) byQrolysts on adaie^ eater In ^ceas in$3icating the presemte of )C»H< » eleaental analysis resnlts (table VII) also prove; the stroctiare. Hie i*r» analysis by BBr i^thoa shows the absence of and )C"0 bands and the presence of a a&v strong absorption band at 1660 tm"^ indicative of )C«S< • the n«iii«r» speotra consists^ of signals occarring at Sm 9«i ( j m lo Uss, a« A)t S^ (J • 19 Hs, d, B}» 7 «90 (StC) and g« 7.03 (J • iO»74, q I>) in trifltioroaoetio acid at 60 Tariaa* fba assigiw^ts are nade as i^own in conponnd (!!)• spectrua in aiethanol consists of a strong absorption band at 283 m indicative of • s.p»r» spsctruB ^ows no signals* The x-fay data eflitaiaed (table VIII) are different than those obtained for diphenylanine perdilorate (table IX) • Thus x-ray data indicate that eonpound (R) i s a new ciystall ine product* Ibe similar cospouiid bave been isolated and identified by ieonard^ et a l . Ternary iffiiniun salts obtained in this class are very stable in air*
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5 8
' o o
St o o X
oc
vO ? I
2 UJ X o t/)
o
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5 9
Mktt oiiier oisanlo p«rdblorQte« tb«3r nay be •uitalil* for ttvlng fhuy my a l f o tie in eyatbetio oHesistiy beoattsc
th«y are veiy prone t o niioleoiiiiiltc^ atieok*
eeocukd o l s s s o f dii^enyliiiBtnfM-eia^yiie i ^ o t i o w depeiKts
on tike fonratioo o f bigttly cnstable and doliqiiesceiit ternary ialntcie
s a l t ^ e sa l t s oay e l tber autosidize witb &t«osp!ierlo ojcygen
t o g ive a (deeply ooloored ooei^otitiil ( f ) o r aectHspose to r ive the
reaotanta. ^ e ateise ao ontaixNsd laay aotosidise t o gtve a deeply
eoloarea coapoand <p) and! the alddiySes to correapoiKllti^ acid via tbe
peroniae free rad iea l . th ia type o f t e m a f y ifsinira aalta are Obtainea
froiii tbe reaottoQ of aipbecylsasine « i t h p-diatetliylasiEif^enzaldebydet
bensaldebyde* O-iranillitiet onisaldebyde and aalioylaldebyde*
t«UC* atodiea in aetbanol ana oblorofom showed tbat the yellow produot oonaiatsof green oonpomHS ^ a t titzma blais^ green te air (ef value i s zero) and dipbanylimine bydroobloride (nf value i s i ) . Ibe yellow product waa dried at 25 C f or 2 boura and then ita x-ray pattern waa reoordad. Ibe product waa fotsnd to be oryatallioe (fable oolam t ) . After 2% boura drying i t tnma partly green and partly pale yellow. It waa also a oryatalline produot (fable X, eolian 2)* After % daya drying at tbe aa»e teaperatore i t tarns blulsb green mnS. fotad to be poorly crystalline (l^ble X, eoloMi tbe relative intensity of the x-ray linea for tbreo fbaaea have been Riven in table X7 • X-my data recorded in table X ^ re corresponds to dipbenylaaine bydroebloride (Asm 5*0326). On the basis of these rtsnlts i t aay be eoneloded that tbe yellow prodnat ia a nixtore of Bon->oryatalline ternary iMiniisi salt (s) and crystalline
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GO
dipbeoF fiB iu^ hjrdirootilortae. ftin yell&v %9Vn&ry teiniiai mlt rapidly miMzes to grmn eotspotoia (T) an& aiphmflmtae br^x'ooiilortde slowly
i^xMiren t o him eiMipotiod <P)« fti« reaettoii t e p o s t o l i i t ^
seti«»i»»7 mdbmm^Brn For green nonpotmi ( f ) i«r« ®i>«otrt» Djr mr
aetltoi eonaists of a strong mA hroQ& bana inm 1637 to 1680 m'^*
n*m»rm @pmtvm in deateratod di^otliylsttlpboxiao am m 90 Mis varies oonsiets of a ntgiial mt 6 » (a « 20 OS, t , 3 FisK 0» troattag sro#ii solution with ssiius dost dooolc^ciiEattoii oooora* el^^iitol analysis results ^ f or oospoimi ( f ) are given ia taHle IX.
flia iotenae oolour of green pro^mt i® ooosiatetit ifitli laxge oimJt^Qt^ ayatea of E»ittor ioaio etnmtiire ( f ) » fhia type of oolotir stuff bea hmen atadie^ by Mtrnm^^ at al« Sti^alli mm Avarell^^ ftav© rew3t*feea, «tli® ^ i f f ^asa prodiSKsefi l>y ocmtienaatioa of as asioa witli @a al^^yda in strcmg aeiS aoltttion* oeii be osiaizad liy atsosptiarie o smm to giva a oolouraa mterial**. Sinilar o^ision baa also baea givao liy
fba eoloiir of tb© osiaisad {iroatiot i s aora iiitaose tliaii tfoat of the taimary imiaiin salt* fbaa i t oao he asaa for ^ aaasitira eolourii^trio detaotion mua dtatefttiaatioti of amiaea and aMdby^ea.
oxiOatioa oaotira at a vary lii^ii rata in diiaatbylaalfoxide, ftiaa i t saama to lia a good analytioal raagant*
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Gi
II 3
X o o u
6
u < o o M z Ui ca
I lU £ UJ X o 4/1
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G2
C H N
( 0 )
IMINIUM S A L T (S )
C O H - N
Nf'
( ^ C O - N H
-H
^ C O - N
t
S> ©
/ C - N I 0
^ GREEN COMPOUND (T)
2 H
CM OH N (Q)
SC HE ME - 8
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G3
ftbltt TIX «> El«Mat«i SMI lysis r«a«lt« of coapoaad <K).
I 1 Elmsiis ronad (IS) Stqulrtd {%)
C 65.%0 65.70
B •TO
H 3.7% 5.60
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fttliltt VIII « x-ray data f o r ll-oitiiiiMsyldetiedlpheiiyllatiilun
perch lorate.
G4
— - ' — • » -vmluwm x / l o a vaiwm 1
l / l o
i2»9m 9 2.882 8
9 •817 1% 2.794 11
9.017 30 2.761 12 7 .019 15 2.696 6 6.80« 13 2.619 12 6,320 14 2.493 5 6.063 19 2.372 7 5*^67 10 2 . 3 ^ 5 11.951 42 2.231 6 4.766 40 2.102 6 %.571 53 2.013 5
43 1.458 95 4.267 48 1.45t 23 4.111 35 1.414 15 4.037 39 1.403 15 "5.863 36 1.392 86 3.767 51 1.383 95 3.705 32 1.362 100 3.559 20 1.353 99 3.42% 16 1.323 95 3.299 16 1.320 74 2.252 12 1.317 95 3.076 1% 1.310 60 2.976 15 1.304 20
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Go-
m i * XX - X-r«y data for di^issorlaaiB* percislorate.
d valfiaa 1
X/Xo d vnlaes I/IO
s . s a t 14 4.037 63 8.036 100 3.897 20 7.2%8 16 3.645 19 6.505 14 3.184 13 6.062 11 3.25S OS 5.S24 25 3.076 17 5.467 10 2.995 15 4.87i 15 2.938 9 4.716 30 2.864 07 4.525 23 2.777 06 4.436 61 2 . 6 ^ 13 4.267 20 2.453 06 4 .238 29 1.793 04
4.149 24 •
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fttbl* X - X-r«y data of li«iiz«ld«liy<l»»<llptienylmiii« bydrooblorio sold product.
G o O
Aftor 2 liooro drying , at
I t Aftar 2% boiira drying Aftar % daya drying 9 A
a v ^ g f ^ ^^ X/x<
aa» 7.2%8 19.8 m
6.505 18.0 6.505 19.8 - -
5.675 i9«S 5.7%9 28.8 -
5.%66 20.7 5.%67 3%.2 - -
5.063 20.7 5.092 28.8 - , -
%.%80 2t.6 %.800 36.0 - -
« . i l i 3%.2 %.ill 61.2 - -
• • %.073 57.6 - -
3.93i %6.8 3.931 100.0 3.931 32.% 3.6i6 23.% 3.616 ^ . 6 -
3.%50 25.2 5.%77 32.% - -
3.32* 19*8 3.3%8 23.% 3.206 19.8 3.i62 27.0 3.18% 3% .2 3.18% 18.0 3.il8 18.0 - tm
3.015 IS.O 3.035 16.2 - -
2.S82 19.6 2.882 18.0 2.900 16.2 mm m 2.829 10.8 -
2.7%% 18.0 2.761 25.2 m -
- - 2.712 23.% 2.712 1%.% 2.696 18.0 2.605 10.8 - «
2.605 1%.% 2.%66 9.0 2.%%0 12.6 2.330 12.6 2.3%2 12.6 - •
2.285 12.6 2.296 10.8 -
- 2.27% 12.6 - •
2.199 10.8 2.106 7.2 - •
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6 7 Tlibl* ZI • eUacntal analyftts r««uU« of eiwpotiiul ( f ) .
' ' I ' ' ' v EUsenta Pound {%) B«quir«d (%)
C S%.%0 85.50
0 5.75 5.40
n 5.10
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81
K g r g R E K C E S
eoap f)c»«ie»k«0«, Chtaleal Xiidie«tor«» tondioiiy 1951t 171* 2* Qnmbl, ! ! . , and Qiir«fllii,S.Z»« Aaal.Cli^** i966« ^ ^ 1956. 5 , Qtii«tlil,ll«» Qtir»t]iifS*l^«t and Siiif6al»S»C*f Aiial.CliiM.Acta**
W l , 561-67. Qoraabi^M*, and fiiaii,I»A.t 2.ABal*GliMi.» 1978, 289. 282. ItoaoaatT.v Ctoda»T.« and liBkatMura»!l»» Cbt»iea2 & Fbaniaeattfleal Bttllatliit i960, 8(9) . 827-29•
6* MoaoaayT.f and SslcaiitiFat;!., Cli««ioal & flianeaeeatieal Bullatiii, 1962, iO(7).
7« lfaoaiiiiria,?.U, Anai.CiiaB*, 1918, ^ %7* 8 . BltiiDO,S«, Miraya»a,!I«, and Klta!iaiia,R*, Japan Aoalinst,
1956, 1 , 07. 9 . LaoaardtN*J., and Pat^atalia,^.?., J.Oyg.Oia*., 1918, 2^,
10. SelitaMietiar,«I.C., *Par^tlorataa tbair propertiea, aMaufaetitra and aaaa*, Htlntbold Ptibllabing Cai^ration, Hew Taxl , I960, 138.
11. AeiieBa«:i,R.M., and Tamer, ! . , J.GHrtniatog., 196%, 2» 12. 8trattli,C«A., and AiraraIi,P.B., Aaalrticai Cbaviatiy of
Hitracan and ita ea»potnida*, Vil«3r*Xnttracienoa, Londen, Part X, 1970, 276.
19. Faisl,r., *Spot faat in Orfanio Analyala*, Landon, Savantli Edltian, 1966, 382.
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6 9
pETECfioK or mm. omAmc ACIDS wim O nmmimwiNOBmMWmtm: in ACKfic Amwmm
p^imetbylminobmmiaetyae (p'&iB) is o well kmm eoloariog
reagent wtiiob i s being o s ^ f o r ttie detect loc and detenstoaiioa o f
amsmrom oi^aolo oos^otmiSs contaioliig a i f f e r e o t fanotioiial groD^s^.
l a i^romati^r^plirf in t irdrodilorio aoid (OJrltcii •« reageat) Ae
a m i l I m o ^ location agent f o r a «?ide mriety of easpouikds iooludit^g
amities, imolern^ l^rro lcs« oertaio asiiftoaoids aisl tetracyc l ine drt^s*
|}*mB in Qoetio sitiyarido i s a l so a well iEnotro location
e^eiit f o r aroylsljroiiies and i s a lso imlitobla f o r the l ooat ioo o f
aoi(20 o f tHe tricatbossylio aoia o^^la ( c i t r i e * iaoo i t r io» a c o o i t i o ,
2*0«0glatari0t c@al€mo0tiot fttsaario etc •} ais^ f o r oertain otber
oigfuaic aoiSat f o r esaeple tartnr ie , l a o t i e , |3tiei^l»laotie» aialoaio ato.
|h»imB i o aoatio aiiiyarido-prt'idioa baa bean oaed f o r tlie aatiffiatioii
Of tiippnrie aoia in beraan orina» notrevar* a ayatawatio study
ragardiqg ttie oaa o f in aect ie axUyiSrida f o r ttia dstaation of
aoida baa iK>t bean reported so far* fbarafore an attaapt baa bean
sada to explore the f a l l m m l y t l m l potential o f tbia reagent* fbe
resolta obtained are aiMBarixad in tbia Cbaptar*
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7 0
E X P E H I W E I I F A L
wt<rial»t All c^Miioala and raaganta tiaaa vara of aaaljrtlaal grada. A Haatiag Block Alualnliin th»% waa tiaatad vttti a aplrit Ia«p to •aintaln 165 * and a aplrit laaip for avaporatlng tha aolatloa vara uaad* Aqtieoua or attianollo aolutloii of ttie taat aiJi>ataK>oa (Iffi) vara itaad* In oaaa whara It «aa not poaalbla to prapara aolntion, a aaturatad aolittlmi of tba aold vaa aada*
F t t O C E P P R B S A H P R S S 0 I. T S
aaaaral prooadorat flia taat aii>ataiioa aolntlon (2 to 3 dropa) vaa takan In a adcrotaat tiAia &o& avaporatad to diyaaaa hy oautlona dlraot beating, ooolad and tban dropa of aoetlo anl^ydrlda ware addad. ma ooloar dairalopad at rooa t«iparatiira (30*C) vaa raoordad and than tlia oontanta of tba taat ttiia vara baa tad in tba baatlng bloolc f o r 5 nlnutaa* fba colour ao datvalopad waa alao notad. fba raaolta obtalnad ara ^oun In tobla XXZ* fba taat atA»at8nea aolutlon (2 to 3 dropa) and a^oal voluna of an atbanollo aolntlon {%$) of p-QAB vara takan In a « loro taat^tuba, anraporatad and tban tba abova prooadart vaa ttaad* fba raaulta obtalnad ara abovn In tab la XXX* fba I M t of Idantlflaatlon vaa alao datandnad by tba abova prooadura.
Pataetlon an aanart A taat aolutlon vaa apottad on a papar atrip of Miatnan llo.l abrotMitograpby papar vltb tba balp of a eaplllarr* Xt vaa drlad and a drop of tba raagant atbanollo p»lMB } AC^ it It5) vaa plaoad en tba apot wltb tba b«lp of a aloroplpatta* Iban tba atrip vaa drlad at 100*C In a alaotrlaally aontrollad ovan* A rad
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7 1
spot Indloates the prosenon o f o l t r i o fti« IlHtt of i a e n t i f i c a t i o o founO to b e iO/«iK« Slni larly tartnrie aeld , I s oo l t r i o eo id ,
c>c»tEeto@latario ac id , ox« loac« t i c acid oto* mere a lso lie detected*
Peteottop on TM; plat—t A teat ao lut ioo vaa apottea aa above oc a
a i l i o a ge l mprmye^ vitti the reagent cM>ntiotied above ana l^en dried at
iOO^C. A red spot indicates tbe preseaoe o f c i t r i o acid
Sieiilnrly above sentiooed aoide ire re a lso detected*
Bifeaviotir of laiaoallaneoae cwmocodai A atraDer o f typ i co l orgonic
compoonds were tested by tbe reoomsjended procedttre ar^ irer© fotmd not
t o inter fere witti tbe t ea t , tbe fol lowiog ca^^tmds «ero tested*
Anioesg A » l i i » e , diotby} o r ditEtetbsrl mine^ dietbaixol oQiue^
t r i ^ t b j r i ami He*
AMdeai Saiicrlamide* aeetaiBide» benswidc .
Alc<aio3.a8 Sfetbanolg etbaool , propanol, bataoot*
Catbobydrateat Glooose* Bmromp lactoae*
Bat are I fStbyl f o n ^ t e *
Etbers Etber.
Hatrocyclic bases Pyridine*
Hydrocarboa aad the ir derivativaai Benaceoat nitrobenzene, cblcmbenzene,
0<-toludlne, carbon tetracbloridet l iquid paraffine*
Ketoaeai Acetone*
l^enol and tba ir derivativea; n ieoo l , catechol , S^bydrozyquinoline*
Hie folloi^iDg covpotmda were alao tested by the procfdtire
and vera foaad t o inter fere «ritb the teat* fbe co lour developed l a
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1 - 1 r )
( ii
gl¥«o in the paraiitii«si«. mpbcnyl aiii&« pjrrrol (V&S), indol
r«80rciB0l ( e ) , p-iiitroph«iioi
Alibreviatlous used a i « defined in tal»l« 1CII.
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7 3
P 1 8 C 0 8 S 1 0 W
mwltm rtoordftd tn ta1ii«« XII and XIII give tti« folloi»it« points*
A% room tmmpmtmtnrm (30 C)t ACgO does not ooloar with aoid*. gives a vary brigtit oraoge colour wltti bailyliario acid only*
p-SAB-liailsittirio aoid raaetion^ i s a vell-lmowii one end Ciea been used for tlie dateotioo of barbituric aoid (Uni t and identification iO/ce)« IHmo in tbe pretence of ACgO givea tbe aoae result.
At iOO*Ci ACgO does not give colour irttb acids, gives light yelloir or ligbt red or light brotm colour with soGae isore aoida* p*mB in tbe pmesence of AC^ gives colour vitb oltsost a l l acids under studsr*
At t^S^Ct ACgO gives tbe siai lar results as obtained at iOO*e* P'HIIB in tbe presence of ACj^ gives tbe results es aioitioned above at iOO*e« flowever tbe sensitivity of tbe colour reaction i s bigber at tbsn that itss obtained at iOO*€«
AS wntiotted above p-QAB in ACgO gives oolour vitb various acids* Bowevery i t gives distinguisbsble and intense ooloar vitb oCrketcilotarie acid (Br)« oxaloacetie acid (8r) , tartaric acid (Br)* c i t r i c aoid {m)t isoc i tr io acid (DR)> cystine OCl (DB), i - lysine (Br) and barbituric acid ( 0 ) . tbe l i a i t of identification for c<»icetoglu-taric* c i t r i c and barbituric acids was found to be 10 g* 9Ag and 9/^g respectively* Obder this condition tbe reaction beoottes acre sensitive (5/^g) for barbituric acid than that reported (iOykg) in the literature^.
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7 4
th« follQViqg •dvaat«g«» of thi* proevdtnr* tiave l»««n aolii«v*tf praotleaUy. i»*mB in AC O ean b« u»«d «• • looaUon r««g«nt for •oidc (oxoopt lowor •oldtf fo isto , Aootlo moa ozaUe) uodor
oan at»o be umiA ac a looa^on for the «tiov« aolda on allloa gal and oaUnloaa Tl£ plaUa. Ilia taat oan applied to taat tha prasanoe of o i tr lo aold in laaion and tonato Jaloaa* 9ba papar otironatograpliy raaulta Indioata tbat rad prodiiot (Attained from the reaotioQ eixtore (p»mf)«>AC^oitric aoid) ia novea ea a aio^le apot in aloobai and aoetone. ftie red product ia abaoilied by botli the eation toietianst reafna (IKwex^SO^XB) i o B^ foxn and tbe anion axebame reaina (Oovax-it^JCB) in CI* fom* It ia fmoim that higher aoida oonvert to their anhydrides by treating then with A6jp» Citric^ acid on pyrolyais givea aoonitio and itaoonio anhydrides* It ia also
A O tcnoim that ACj^<-htgher aold reaotion oan he o a t a l y s e d " by a baae* fbe higher aoid anhydrides are so obtained oan reaot with aldehydea* niereforet on the basis of these experimental results and the faota given in the l i t em tare the reaotion sdieae^ oay be propossd for this oolonr reaotioas«
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( o
CH2COOH I
C ( O H ) C O O H -»- A C 2 O I
C H 2 C O O H
•C H? II C - C 0 +
I > 0 C H2-C0
( i )
I • H + DAB V
C H - C O II > 0 + CH3COOH + CO2 C - C 0 I
C H 3
( N )
II C —CO I C H 2 ~ C 0
I CH
3>°o C - C O I CH
R E O P R O D U C T (HI )
- h e a t
S C H E M E - 9
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/ D T»lil« XXX - Ost«etioii ftf Ma* oaifKixyUe mclA mt i05 C*
S l 7 Aeldii ' ACgO ' ISt p-MB iHimBAC^O lH AMOS
* I » m nt Cd Ot CA fit
i . Ae«tle m nc NC NC LT NC NC 2. Afteofliie ht Vf LT hi LT LT LT
5. Btnasolo nc KG NC NC LT NC NC
Clmi3^o m NC NC NC LT NC KC
5. Fonalo NC HC KO KC LT ISC NC
Gallto KG NC tJO NC LT NC V i a
7- GlyCKKSrllC KG NC HC NC VLT NC NC
8. lAotle HC NC m :?c VLT NC KC
9. Nicotonlo nc SC n^ NC VLT KC VLV
t o . ra-HltroHeosolo KC NC LIT NC NO NC ' NC
11. p*HltrQl}eiizolo NC HC VhY NC NC NC VLT
12. Pyrtnrlo MC NC W NC LT VLT VLBr 13. ^ l l o y l l o SC NC no NC LT NC NC
1%. Adlplo NC NC m NC LT NC HC
15. Wmmrie m NC HC NC T NC NC
16. GXtttarle m NC NC NC LT NC NC
17. VhY NC hY LT Br NC ^ 18. mUie nc NC NC tt LT SC m
19. Halle NC NC NC m LT NC MC
3 0 . Mftlonle li) NC NC VhY LT NC T 81. Qxalle HC NC NC NC NC NC NC
22* Qzaloaofktle lar HC NC YhY Br NC lar 23. flitliall« NC NC NC NC TLT NC NC
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7f < /
(Taliltt XII Conilntied)
Si . No.
Acids 1 r ACgO P-HAB ACgO i p-mB* AMOII
Cd Rt t
Cd lit Cd f i t
24. StMscloiaio m KC m KC VhY KC SiC
25. Tartaric tr KC m KC Br m KC 26. Citric m m m n o n ha n
27. Isocitric m KC in hd on m MSr 28. Almiioe m KC Y VLY Y m Y
Ai^enino HCl tt m hY VhY Y KC Y
Asparatic m m hY KC hn NC m
3 1 . l-Cystine KC m m %C Y m NC 32. Q^tloe RCl 1.Y KC tsr hB m BC Dr 3 3 . Olataofio ^ tJC lY VhY hY KC KC 3%. Glycine m NC hY LYO 0 KC tY
3 5 . m KC hY m Br NC LY
3 6 . BarMtnric VLY 0 0 0 0 0 0 3 7 . Boric m KC m KC NC EC KC
3 8 . Bipparic tt m m NC Y KC m
3 9 . SnlpliaBio hY ir Y t t 1-Y hY
40. Urie NC m m NC NC NC NC
Br m Brown; P • Dark; L • Ugbt; R « n«d; O • Orange; Y « Yellow; V m Very; MC • Ifo Colour. Hie foratr refers to colour «t room teaperntitre (30'^O ft heat at 165*C. Rt • Rot; Ctf • Cold. MSJi m Acetic anhydride; A»OH m Miyl aleobol.
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o
m b l e Xlll " Oei«otioii o f carboxylio acid at 100 C.
SI . Aeids ACgO • i<? p - m n V c g O • p - i m s • aipou SI. Aeids
Cd I
nt Cd Bt
t . Acetic RC NC KG KC
2. A800lt>lc VLY VUJ iBr
3 . NC vtx KG KC
Clnni^o KC LY EC KC
5, Foralo KC tY KC HC
6 . Gal l lo VhY VLV nc KC
7 . Glycatjrllo !«S vm KC NC
e . i4IOtiO tm NC KC
9 . Fiiicotcmie nc KG VLY
1 0 . m KC V t r
1 1 . p-BTltrobenzolo KC v i T rjc VLV 1 2 . Pyruvic Lir IS Vht Vhf 13. Sa l i cy l i c m ht vm Vh2 1%. Adlplc HG f nc SC
1 5 . Ftnmrlc W VLY uc KG
16. C l u t a r l c NC v i B r KC KC 17. o C . f C B t f ^ l u t a r l c ISC o r SC nc 18. M a l a i c KC VLY ICC VtY
19. f m l l c s c T nc HC 20. N a l o a l o HC y nc NC 21. O x a l i c nc N2 nc SC 2 2 . O x a l o a c e t i c VLY I B r NC VLY
23. F b t h a l l c nc Lt NC NC
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/ 9
xni ConttnwA)
SI. Aeida Ro.
ACgO • p-DAB ACjjO • t% i>»mB • Amm SI. Aeida Ro.
Cd fit Cd m
Sacclnlo NC IX m HC
25 • Tartaric NO 10 NC NC 26. Citric la 0 NC 27• laooitrio NC E uc NC 28. Alanine NC ht m NC
29 • AHiealna HCl L? Uf m KC 30* Aapartic uc UQIT NC NC 51* l-cystloa HC * KC KC 32. CysUm BCl ViiT lar NC Vht 33* GlutaiHc KC ht NC KC 34. Glyoine NC 0 NC HC 35« l-lfi'aln© KC BT nc NC 36* Barbitiurio 0 0 r 0 37. Boric t® NC NC NC 38. Hlf^nrio NC Tf NC NC 39* Sulphaaio T T hV vut hOm tiric NC HC NC NC
0 • CrveM* n««t at 100*C« Cold at rooM taMparatiira (50*C). Othar abbraviatioaa iiaad ara dtfinad in tabla H I .
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8 0
1. lbitiior«,B*S*» Hoti«mBa<l,A., Pimka«li»A«, noa Kmmrt^K,^ <I.Cii«M*Soi«. (In PrwiMi).
2« Itordmniy^.y m& liordiiasyR** (Cliiriig.CUfiio Saipetiiere, l^r is ) Patbol .et . t i io l .smiie iiop.t 1960, i059-%l*
3« Prior end ftelvaSyM^e*, (Service* Bioctiea* iilebfm, l^ri*)t J.ctinxiatog^y 1961* 505-i5* Arastroag,!!** and J«6io«Ctiea«t 1956*
218, 895.
ObnarlyS** OgaiayH** Itee^*!!** ana S^ratS**
1972, 6« Eathoret^^S.f mU QaresI^ltH** S»AQal*C3ic@.,
1978* 502-303. 7* Flnar*f*t.«* 'Organio dieslstrir** Voltsie X* FHftli e<lti.* iDisi iicsii
Oroiip Minted* 1969t • 8* Patai*S., eb«Bl8tfy of the <iail}oi^l group** Xoters6l<»ice
Pi&ll^era* 1966* 593. 9 . Paial*s.* 'ftie eli«al6trr of tlie eaftioxyllo groopa & Eatera**
Xntersoleiice Ptibllsliers* 190t ^05.