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ktl urd€rrtood. Trror€ !r. c.rt.d. rhet.tr.a .A.!t. tbat b6r.b..! {6.1 rlatEt vtru... rulb a. rqll D* sd {n c.ri.tn tcr.ol @cor. ltdboran ha. b66! u..d a! dtlr@tlpd .8.nt r .rdo.rc'paoD61.o. lo "o.erz,!. a..t.cted rtrr or aoc! drus. 1.

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or .,Itcylarr..-r-t-asprla iho rrndc iFug of the brld l. c6r-ol bllltoht ol aabl6t. .v.!y yod. It t. atl'rrF6ti

1.J6cr scrrub€.tr sc. a6r:-o J i{.1tt5z,EIiorrG.B.ttB6at tc,ti.flitch1ra6rJrA..r.ch€!,5o..71r{11r195a.!'"sr-porlu o! 5+lorc.Dtorstn.'^e.ta.t.^..d.sct.5Or18t.195!.{.D!.s.!r$.Pluadr.Arohrc.s.rhy.toL?6!toitr1899.5.G11b Au.ch.E.Phe. 15or 9,1859.6.,rotdr J.i.D.flai.dr B!t!. ]I.d.Jt arrglr 1911.

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It.ttD.ur th.rofor€ thlt rho @.t potet tlL..rfurtdru!. 6a today nav. I GoGon D.orer.ry of coordilattd arld ch.t.-tror of et.t Lo!. ,lti th€u.tve.. Tn€!. rr a Srear !..it lo,r;---n-r' thwertts.tion tlto tho lhy3ico_cbcqr..l propdttc. ,!dtb. Drt.. @d !.cr!{tE of tn..€ .t ua..

AUd6r t. .!. of rhe co@otr .F.t oD.. ,bi,oh @ta..tit..la tr tb€ ao!6 oa.arh€rr blr.to.lr Gcr.aa, cholr:t8r aattEred |d othc &I!d''.. ,hl.h .onetto€6 p.oft .llDprtlS 6 f,.t.trIbo@ad. oa dlaf.!6t ett8.u ca! produco .U.rSy. 1!.r. data.tcorUrl t. dut Dsttcl.r .!t.r poll.!, D.rn&.. oat @.t rrtF-tetoa.lt t6. fot.ttr Fot6i{ drrch @y lot ,aalo€r to A ccrtltntbdlvlduat. blo.h.!d..t!r. It i. !6t ud€.lrood a! to h* tbey ..!brt th. .!d !..qtt of ttt. t@nech.Etc.r re..ti@ iE &.t oa tr&..... t. tt. !.1.... 6f n&t.dn€ tato t!. tt..q.. oa aL. .ti.

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aalD.n' i6 1912 partulat.d !b.t tb€ Gau. of oU€ratod arDhyl,.:lo. Ely li. itr . chonlcal r..ctlon ol !.t....it bt.r.-!tr. o! .od. lapoltdt ..I1 oho61..t .pDs.!!ty . 'h:!.taotr!. r.!.-ptd. awr tbout5 lt l. loi .t .u. boh a. t. r.iat th€.. r...Dt.or. d. but 0!6 8re. !t th. .tr!cia. oa blrta4rla rtlt hsatttl'.!r ay doubt .. to th. n.ts€ ot thq...e..ptc.. ni.t5l& aa

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unrorr@(ely.a! for.i6r rrot.1!r loE 6ry tho.b rr{6. -wt D c.B. Foducdo! of ,tibodle.. v.ly,rsai e: : :.ut. of, ot9body @yr rr .r6for.t b. fffi.d rden du.t, Drld .!e _

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r.aclioD vlII not ta!. rl4e .11 .o EEh &tlbody 1. Fodu..d .

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toe aaa Jo*sro h.v. .bcft tb.t 6. .!!r.atrr.l a..t lr'.r.c..odJ, for h1!ta&L.-tl,tc .ctl,rtry 1r th. ol.t,

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tnlt r@h st.ao&r, d. rFodr...t !! .itr ta rt. !od, !, .itaattrDl,o.hoot..l t.d.a:tutt6. f..rl!! oa rDt. hrtotb..t. t. dt,ttor.tblo tblolah d.talt.d Dto.h.Etc6t trv6.!ra.rloD. Itoyr...

-tt3 r-\.i

.cr. bdt.dC. ot rtE rhy.t.clb.rl..l trorsrl.r .st: at rltdar..cct.rt@ .cDtst.r acertd .o4tes, u!fr oa b.6dba .t-l,ll lf, cl 8t..t y.ta t sdd.t.ldt a qr D.t[riotF o, ib...etltri.t..rrr. dr{r..

3. .ttart b.. b..! r.d. & ud. ,eE to i!.ta.b.tb. .cirt dt..o.i.rlou c@tdt! dd acDt16 ooD.rs!. u,l[ .r l

lqrct&i !.a.1 IG, toa.tis ,ttlt ttt .rr!!r of trb rd!c..t &a uolt!.vtol.t .F.tr. oa .oa or tb. .r.tt.bt. 6tt.ll..t!c o. Ett-rrr.t.&ld. drus.. rh€ d.qa. tb.t b!v. b.€r .r-_!.d s. r. lbU.'.!ll&E sT.{rctIrtt r&iJa [d4t

r.pJr-tbtt .!tro_!!l$. b.""ura.vr

l!D--h.ihy.l ..d!o-lhrtttdryr.tbc,

i . t- ( ta /r.DtE.thrr.arEo)-,-rz-DFt.t rt)For,.E.

''l-*:i#,ffi"ti:l-

, 3.jIL-:irL I

rtMlo!|

It-t 77 t-

2- (r{-leDzyrrDtlh(ethv1 jln[dca1lne k€th.n. sulE'lr.rc

2- (N -Ph6nyt -x-b€nzy.Li mlno-mthyr)Imid€20lrn€-

lrlploltdtne xidlocbro!tde

ar dphsy.rpyralbe nydrochlorld.

". jt**ii5},tsgi#l

'o'il: $ff jiYl;3;119'io*

"';-[iift i:ff .xrjiy.iff jl?,,".'"

"'$l"ffi '3J"';x;*svr' t" -IbDz.Y1

l3.N-ri.di,ethyr, 2-pherothilzhe erhyr€n€r,,.,,-r,-drcrhyr r*."",."r_r:rrT!ili11.".

6 eFel| of l1tq.tur. 6tbr6 tn.t vcly 11rtlcb!r. b.6 beeD .to.e tn th1€ conecti.lr.Ortttrr3 ta rtu docto!.l th€615 h.s deterhlred th€.c1d dlsloctotton 6nst.ht6 o! . &.ies

taolhrc dlugs .uch .6 tltretd, --__-' of coturErciil .ht1hl&

.ntrstrno, h1st.ftine Ehd blstrdlao u.. ;t-t""' *noo.,

6s re (rr), Fe (rrr), Hq (.'l?ri ,rr, .j:':"r*;:: t'" **

L.c-6d.dsl4 ct.at h.v€ studl

-u,",.."u ;;r:T,:::.:T:i'l'

tttt''-, (rrt .nd rd (rr) i.c.rod!d!r5 n." .r- "o*_d.e n1s studle! to cd(Ir) lnd b.. dc.elhlned thoso !ofe.o-

a-ll th€ d.tehlblt1on6 1D tl|1s blk b.ve e6 dor€

_rlar-

!a FteDt!'ct!1c o! pE tteatld Ettbd. Thlr e€thoit t|!.ollglr|alrt eq}r..l'.d !t Bl6r!q'o tD hls t.Dus roltr fo! tlr.0€t rrllotio 0! to6.ti6 €!rt!nt5 0t rr!1 nfitn€!.

tni. Dthod l|€. tE o usd h.r€dth tbdlttetldsr!.re !€54!y. lbts ull,t b€ 4ldent f!o! t|te !r!u5.r ot ths€lF.rlD.rDtal .€cr16.

the .tuiry of the iD&.r€6b&. D€a qd.!t.|,qt ltth a vt€r tolrb(llnq slt ! of the blecuLs.

lnd rlt!41o1.t lFcrr.una'.latanit tt!€ tlatula ot

13 Adth, bctror, di!s. I(6a4s stst€ rjlrlvr 1960,14,a.c.rrribdr.. t.D.r.!bn5 a. t.D.o.!!!.n, r.ch€B.soc.1962,l?76.r5.A.c.rod!d. .nd J.^t!k aaesiy, !r.ch ce Eoc. 1964.405.

'"'i:iJI"'H; :f:'tffi,fr;;igli h iqu.ous sb,.,r'q,n

thta eork mr uddls.tltr6r| 6, F.rt of .chs€ o,studylng the chelo4nt protF.t!€s ot sE .ntlblst€ot!€.r

1.h€ €gulllDato 1r o{Feou! $Iuttd! ot e .€.I...bt1r|taut|raltc dru9. 6tra tb.i. ch.l,ct€r ,rtn varlo!ct l. sre sbdted.

;cta- bo6e e$dltblte, cbolate to.D6tldt rlthc! (rt), Ni (rr), c6 (lI) Fo (rt), ard ar (Ir) nsve be€n€sll:lnea ln aq'rou3 r€atl. !'l potenttca€tll. tltr.tld

a abt u6rt .tuc, of the ultr.vtoter, vl.r.tl€ dtdllllereat r!.ctro of t!€ trrro Gqtorlrds t.6!o iEab.1be trdbl,€o of <arrF€t6t1e. tbidbs ot the !€t l6ht1n1.t€nrDe s, .1.o drudleat.

EXPERI]I!NIAL

!. r*flI.ltl/a! r,ltD alGl/yals.

Al,r the .ntlbidt6ilDe, uFd 1n thls p.ojecr *r€6uF9I1.d !t th6 dlttelent cbeilcal iadusilles lD the t{rc.ttorE 60 Do luthe! Friflc6tlon F. rdlol,r€d.

the abtlhlstao',ne8 rer€ glac1ously pre*dr€d b,the loUorlDs nauuf .cture!..

r. .rlDd!y1 lrct p€sk-D€v1s ! co. xa!6chi.2. B6.ad.yl ncl p6lke-rEvir 6. co,K.!€ch1.

!. I!1plolldlne Hcl !u!ou9b i!e1.to@, (ar.chl.a. ChlGcycrtzlne dcl Bullougb We1t.corc, xalscht.5. xhtszollD€ t€tbane Clba (Fk) r,tmi t€d, rarscbl.6. rlFnlr:hln€ lteleate EQA, xalnchj,,t. chLolopheot!.elle !9L?, Aoachl.d. dprtsyrF!-a11ne 5.X. ! tr i.1!!ch1.9. 1b€n6.L1d1n€ Hydlo- sandoz, {D.k) Lrar,.rahstblo.gen laltarate.lo.;lt6roune dcl Eoot!, r\.roo!1l.iott!1&Dt 2.},nt€!gen

l3rD!€the21n6

l4.pi€nellen

s1.ce th thc e& o! pl@1tdi.€, chloloph€nilaarneml6at€, ltFtr l,ial1ne Hydloce. t rtar.re. ,rlot!. ir rtE*c6*s .ro \h4r to loln coripleE. rtth et.l t@s17, ttE

exchanFd qlrh ch_lori.& o ,5b€rllte I&r_4oo!€.1D thrt h.d Fsl@sly be6 &tolrteal ytrh cblorlik th€fin l cooc€ntlotlon *6 iietehhea rFctrolirototutrl,csl,tyat 252 &n the Ev€t€nstht?. r$t€l .nil C.lvln, xcbdl.trv ofcohlgDd.. PEqtle-clu, Inc;eer

tbe rete1 ah€1.t€loak. 1952, p. s1?.

oa dao6 .b.orptlor for Ph€n1rdln. t6r6.te. (tttl. .rthcttond6t.r61nod to! th. el€at. *a! 4,58 r 10'Ilt. ooto_l

c!_r dd for chtcoph6rtrdile oalelto ras 5,9O r to_t 11t.d1.-1.n-r. Tfi.naltdtne Hydro8.n Chlo.tde va! ar.rylod by pr..r,p*atlot.t thc chrorrde a. sllv€r chroltd€ lad toud to bo 98,2t6.

App.oxlMt.Iy ceborate f!.6 o.t N sodiu Eydrortdo.olutlon yaa pregded sd r.r ,taldddirod '1th pot.srtu rrydroa6rpth.l.t. of tlly & late lllch ro. p!.elously dil.d at lrooc.

Tho Hydrochl,eio actd roht,'oa ot ato{t o.ot d ea.pr.pd.d bt .tandardirtna FIth !od16 hydrojd6 .otutl@ t'oi.!-

Stdd*d 6utf€r, of a€ckd.n,.to u.€d tbroqshdt th.

stoc|. .olutiono of &tal ion. oa approrl@t6lt OrO! itY€.o Pr.par.d ty ilt.dolwlua th€ cor.o3londlns D!.I chlo.lilorrtlro d€aot ton. soluttod! rere !t.!d.!dlzed by el..troAfaeletric

Pho.phato buffor. of o.1 str6nath v.r€ seil apar6la-tot€Iy f! rsst.! ol ptt ? for utt..ytolet lpect.oprrot@.teic

Alr sotv.nts u.ed rsre of .pgctrolrade qrauty sup!t1.d

Doqbry dl.till€dr d€lo!1sod vater ras u.eit for p.td-ti@tr1c titlatioB a..l rp€ctlophotodeiric vork.

rr4-Oioxan. ya! d.i6d dnd !6di6til1€d.

(1) Tltlation aF a!.tu!.Trr. tttr6tlon w.5sel !.:ed ra]t6.t b6a}.s

rlib t!I6t .nd outl€i f.r .tr.qlatlDs thsrnostat.d 'ator fro6 .!1ller.-a!d6!sors rl,o-teop€ratu.n bath dairLarrod ,t 25: O.o'oC.

It. Dtaettc cov6r of the tttrattor we.!.l lsd the .Dp-toErtato lubor of hole. for apalr of B€cxdan crt.ns16n glalr ald.!tuat.d crldel ol6ctrod.r 5 El Di6o l,66tt.t a frtttod a1...Aa. r,ubrrle. aad, bont sla6s lod to d.ra.h dlopt,€rr of rh. ttira.th8at.a f.oo the baott6, Th. bugrta rd co@ct€d.t dte tol| t.th. lodtu hydrortdor ftod ,h1.lr standsdlodlE lryalr.od,d. tolutior coutd to the bw€tto byDr6ssu.-.lDrlonrrat|, Ardr€ftr lyona and o'Bri€nt J.chs6.socrt962.r?76.

pli 6.asu€6cnt6 ,ore c.rrlod out f,1th aGs equirpcd vlth a gtr.E oroctrode ed

. , "-:lt"n..JJ-r t\

B6ckrdr! DB o6t6a. !.ta.t.d c.IoE I

Tno pH o€t.! 'a. .tddddlzed vlth aqu6@..tdd{dbuftors .o''stton3 (pli {,o 1O.O2r?.o j O.Ogr .!d 9,O + O!Og)cont'slison rtth stard.rd buff.. solurton. of .aD. !H 6t atocwbich vcro prcp.!€d buftGr pordei. rlhor6d tbatno rdcall.!.6tton3 fer€ n6c..sdy i! tholo DH.osion..

Parfi6d nitrosen s.. y!. palrsd tlEaSh tlo abofttttloiion s6lution 1n ordar to Eatntaln ihs .dboaitioxLd. at@r-ph6.o rritbout Dy lub.tantlat, ow.p6tatlon ot th6 roluil@ ,.n thcrltfotio! vesr€1.

(Ii) sbectrophorooerrtc Apparatu..A lockaan nodel DB rp€crropboroBr€r €qul,ptod i1t5 :

lorr-B€ckban locolder ,a. u.od ro! i..ordlng ultraylolot rpsctr.tn dlff6le.t Dedia of tb6 cofpoEd.,

Lat.hed 1,oO co rilica .611. yd. u€.d.A !ork1n-Elo6! nlnfracordn I!f!6!€d r.cofdllg rp.st!o-

lhotooeto. €quipled r.Ith .odt@ crnorld. oprtc' e.r u..d !o roc-old thc tnfrared.pecrra of rb€.ep6Ed..C . P9fE'ITI OI JETERIC TITEATIONS

!il44d Dtrsociatton co4tant.,Exactty 50 og ot th6 antthl.teins. y.r. fl.tshed 6<l

!!t 1n th. tltraij,o! vo.sql cort.1n1!s too,I of d61ontz.d r.t€rdd 5 En of o.ol Hcl,. Thlr f.! rit 6t.d qds. m at@.th6rsof nlt.oaen wt r rtan.la.d O.1 N Naorr u.r,ng r B€or6d lortol GS r,gDetGr. alt ttrration. ver6 pt!!for66d at 2t + e!o'oc.

ono tt?1cal .€t of data t. atv6! ln taDls oa lho

(1i) statilltv Co!.r.pt..Follotlug th6 v€II lo&n a€th.d ttrtrodu.ed by AJ..tu(,

old rat€! extondod by Catwtn and 'rtlson6), th6 ttt ltloe v.r.pe.fordod tn o*actly th€ ,r d.lorl,bod .b*. is lErt

J.BJo.ruD, ttllotdl ani!€ Ford'rto! L Aqu.ou6 Solut1.r..t,I,.rl.ss & Sono copotrbagdi r9{1.

(a) M.(6tvta drr K.'rr.nrlsonI J.Ad6rrch€Ersoc.5?r2oo5|t9[t.

(1,) Erc.rt th.! 1n addttton to rrt6 drilt1.t.n,!€.r od ratdrto Dl ot f!€.h1y dlsttlled 1-4!dlos!e and 9o Dt of watc ,a..drl..l i. addltton to th. t nl ot OrOl tja.aal

''or .ohtI@, t

the tLt.atior v.ra.l.O.O7 rr. add.d to th. .ach pH v.luo. rocdd.d. t]ll.

ds. to .6D€rtca1 obldvatlou of chdt€r(') ddvs Uttlot dd u"'" ({)

"rrot rh. calcuraied pfl v.rue! tD lse

aqu.ou. @.riu Yd. oto? htahd drd the obr6v€.1 val'us! t!Soia v/v Dloxatre vater osdiM .

Th. dat6 ob tr!l!3d yer. tr..t.d ar dt'cq..ed h th.

lho data !o obr.rred 1. ,bom t. tabt6 2 ro to tn

ultravlol€t .pe.t.6 of th6 atlhl.t.DlE.!al6{i rlth B€cxaatr @del BD.pe.trophotoD6ter tor.olui16. rdA-ing f.oo I r to-{ to 4 : r--tr r" "q"""- .orutro@ of edyinshyd.og€d 1on conc€trtratt6..

Starddd .olutlon of llydrochlo.lc a6l.d r6F ued for.oluti6D! urto th. pH of 2 dnd cdbolrt. f.eo !odl@ hydlordd..olqtion. fo! p-!r 11 and at'ova. Ia th. j.rt.h6dlato lsao of trg,buffcr solutlons ot conlt6tri lonlc rt!€nsth ol orl ftr6 urodr

Thr.e.p€.tr. *o Aiw.n ir th. ftau.

sinoe t.s dntih1.t.ol!e. could Dt fo& .opIo!.raaally ytth th€ botal loD .o the !!€cr!a of th. corpl*.! coutd

al.o thore c@poEd! ae not .olubl. b olsantc .olvo!t!oroopt fo'r ,h1.h a.€ aolubte 1n Morhdotr ttr. r!.ctra oould lot

g:-gIB3Eg9_-€3E9!8AiI!?rd6d .p€ctra of the sttbl.t'ot!.r 1616 .D!i..ed

.p.ctrogrode !6ta..tu b.ootde(t.r{dck)pollet! ed tr CHCIi .!d

StDce @rt of th€ codpo6.l. dld not dlr.olv. 1! co@oD.olw€rt. .ultlbl€ for thfrded .tuillerr only KBr p.D.et. ,.ro ur.dr

Tho.o !pe.tr6 *o A:vc! U ftaue to of tn6 apDerdlr.

:)05) n.G.Chdro.r Ph../rTh€.t.tUntvdr.lty of PlttlbwAhr19t2.rr((|) L.c.va! ur,trer .nd c.c.Ha.., J.Aser,ch6Dr soc.?tr{t1.19tt.

D.ULT3AVIOLET SPECTRA

RBSULT9

6. ;CtD DISSOCLTIOS @NSIAi15.

rn the tltr6t1d of lhe .trt1h1ttatr1aet, 6lnce th€r€ aa€

!b types ol compoudB, RH- and Rd; tvPeg? at.rtln9 rron 'cldeLutlona the folldlng equlltbrl! cab !E ultt€n

rri :! Rs*

Rt+ !z- .*o o* E "

rtEle R lelfes6t6 6h antlhist.mlne 6o9oud.

the flrst inflBctld Po1!t h the titration cuwe rlll

ocs! st ! loj.rt uhele:tbe exce6s of hyalrochlollc 6crd and th€

eple! iH*+ hav6 t€e D€utrallred.

For e:c'Fter tbis poht cln b€ e€n in th€ table of

the.ppe.d!x to b€ at 2.42 !!ot naoH to! 1.5o x 1o-3 D1e! of

Dlphayt pylallne Hc1. th€ 6@ut o! NaoH c@sut!€d to toln RII+

6tolchtdretr1@1ly 16 €qulvaroht to 1.14 (5,o0 - 2.42) of

o.oa?s M of NaoB rhlch clves the rcle@tar €tqht ot Dlph€nyl

Py.6l1ne Hcl a6 317.40.

the thsletlc.I bleold relliht of Dlph@yl lryrlriDe

rhta €$u!€a ot the purlty ot tlE aubltance 6. seU

ae abaeDc of a !o$1b1,€ hy.trolye!8 to t|!y €pprecj.lbl€ de9!€6.

the equillblium consEqnte kI .nd x2 @n b€ cal@1ated trod the

data 1. th€ buff€r leilon. b€Id .hd lhe .Iov€ the iDflectldpoiDt t€6tEct1vely.

,t any lblnt ln tlE t1tr.tid.

aR = Rlrj.

rihe!6 TR 16 €qual to.ndne dd RHl+ etc.

@r6trt!.t1d of sntthl.t-.@eutrltloDr o! the epte3.

ot- + cr- - x+ + r.++2srj++ ra+ -----(r)

r! sl !elr!e!.dts. nH' : alR +cr- r (na+ + H+)

lnd s2 re!,se*nt! Rq+ : otr_ - (aht a rr+]

and t! E .sal ns; .r€ negl€ct€d itr tho lllrt hfl€! rB91o .6d

tb. lecoaal Ddtf€! roglo|t r.q)€cttvo.ly, lt c.a b€ .horD tIEt(a-) (2.rr - sr)

(q - rn)(n+) (TR - s2)

rh. .v8.9. v6ru$ oa ri|(r aal !k2 u€ lourd .r€ gLvelr

ih tta loUor1ls t.bL.lhe p!€c!rt6 t.1o.o2 ltr th€ !'k volu€s.

T},8I. I I.

&cllal dllaaoclltlon coD.l.nt. fo! ti3 .Dtlht!t!dln6! rt ?5+o.029c.

,;INI!BIADAI{IdI P\ Plr2

cht oloEh6ni!.etE

D4!h.Dyl ttlE rua€

Phenorl.n.Atrtll4n.r{rblgrn.

s.99 - 9.tb 9,t28 9.oob

LA2 - a,O!r

9.lo - 9.12.

2.24 9.42

4.36 1.66

9.60 -9.65

a.ao to.22 2.45 ?.37-lo.l!' ro-roD

2,-21-

rdrrn-Nf+R

Charse bal.leod_+cl-=c'+ur++ng+tgr . qi- + ct_ - (!!" a-) . a

lad t -1B - xtar

'& t . ti+l ltR_51

a. drAlrLrTYcoNglr{ns.

A&rrolDg th.t both ltl .nil lt2 @ta] chcht€.l€ lormd

rlth tl€ .!t1htae.&rne. 6na th.t tb. nrt'dro1lt1cf€adlo .r€lilnlre b tlE lll sln€ of 3 to 5, It la t ..lbl€ to 6l6rl.teth€ .t€Frlre fot€tro .bn tE|t. xt .oaI x? detL.d tblor.

xl - ln+rt* x n

ltori! r+ + R jl.' **

nr"xi-ri

fro6r|R?R:xl9

rhgre d++r e, t|s* *o ml* relc€€t. €{utttbctuD o_contiltlo||. o! tlE q)ecl€! Bt.l 1@., .nt1bl.t.oln .,x(irltf

h (/rll) i !.EFctllel Y.

j|t aht lDtnt !n th€ tLat16

tRr Et +R+2XR2 +flA'

Da=x +xn , !R2

rb6r€ $r 1. ttE rtotcblcr.t tc @c6tr.tl6 0l tlemt.l la. oth.! t tu lrAvo th. s.r .lfll,lloarre qr 1lillcakd

or_ + dl-. ra'+ Nar + &r+ + z y,nT + 2 lrl* + &l*ed - c!-.2ita+ tR

M r.!,!...rtr.!a+ - rR * dr- -(xa+ + r+) . s

1t c.h be .torD tlr.tgxxl

lrRs + a{RI

r*+m+*nirt t. F!.lbt€ (.€c .t?ddi,:i to.qr.Ga Il- It! tds ol

IhorD qu6r!M6€ tt, tl,r, H+, , R .nd Kl

1R-i(tr---E-l

. aDd ttE .v.!.{€ auib.! ol lbed ll,g.nd. trr Dt l io,;' 1! d€flD.at .r

ro* * lrrl

; .!d pR { = - loc i ) Er. c.l olated lrod thr.e -ttof tltr.t1d ilatl,

r!?1c.1 ..tr oa d.ta r.Ltb !_ .6il pa var,u.r .r. gtv.d 1o/

tabl€! 1 to 3l) o! tb€ lt[raill,x,

-2t--r verauc pn ras Dlott€il. ttE tlors a!€ .horD ln th€

ftlu.r o! tlE .tEEDdt x.

It la Ehorn 1D the ap!*ndta thst the valq.a of pR.t; = 0.5, ._ - l.oo 6trd _D . 1.5 qtve! roq Kr, t//2 los k2 .nd

Lo9 \2 rqFcttvely, plovrdd tne canc€trcr.tlona o! th€ aplce!

m;' snd xR* !!€ reqliqtblo at ; = 0.5 6nd l,.o .elFctiv€l.ytlhe value. oi lo9 r<1, I Io9 KlK2 oDd loq K2 .re qlv6n

1n tho tabl€a 5 to 9 ol th€ lectLo V.

C. UIISIVIOITSI APESIRA.

Ttb ultravlol€t aFctra o! th€ anllhlrtadlnlc olloudahav€ b€s !€olded tn !cld, b.se, beutlal lnd n@ IFIE .o1v€Dt!

rhele !oa3lbl,e. Bufler! of pii = r, ? and l2.o h6v€ be6 u6€d .th€ 6rq'.!ar5ti6 o! th6 aFectra of th€* 6qDsd. t.

6tlaishtr foraad 6a tb€ rledrra ar€ golns to be e8gort!11ythos of th€ .loBtic ayat@ att.ch€d to trP .Elb€tlryl gloup.

arc€pt fo! the th€nott'.!at:1,D6., all the 6qbund. 1n thl.serle. of aDtlhr8t.olblc ilrug8 h.ve been t Ut 6€ boane, p!al-db€r !,lFrlzin€ or thioph€ne.

(1) lbe benr€oe ilehatlve..the* 6r€ the foLldlnc.

(1) cycjlzrn€ (2) chlo.oc!'cltzb6, (t) Ben.dryl

(4) lrlbodryt, (5) Hlstryr (Drph€nyr plllaue) 6nd

(5) Aat€rgan.

All o! the& odlsrlda .hdd dxloa douDd 260 1 2 .b 1.cll, th€ nEdla. the .ciil &lutlon lhora 6 ElrFht ahilt (2 - 4 nn)

tdard! hl9h€! r6v€ lenstha. tht6 ta.d ltateF !e qrqu€6t16ab1y

th€ 260 a b.hd o! lr€DanE xhich oltqtn.tly i3 k!x. Ihl! 1.

hlorn to b. a-A-x' alo+trqf ' dq€ to & c€ued .i@try &rbl-dden r'r9 ----+ Bru t!.baltl@. s{b6tltutid lD tbG b€lz€De abgcbanq€. lbe srErFtly anil th€ electrdlc 6r.t6 to &E €xtst

oaly to €Dhlbce th€ .cttvtty of tl* torbldiLl bsdd' I]'erefot€ !a

obslled 1n th. cae of l4nbdlyl atral chlotqclltlb€ s f!!il

€Dhanc€d tnt€n.tty ot tbtE blrd lr th€Ee @$Dound6 {a= 2o'ooo to

TIF plotonat€d s!6cr€6 foms a 6 PI.tDa! clclatc llnq

,h!ct! Floduc€. tlE oberved b6lhochlortc th1!t o! thta b"d

ben4tr6 - Pvlldlne dorlv.ttve6.

ltF @irPosds 1tr thi. lnclude the folldlDtr:-

lb€trlraoia€. chlolPlsirloln€ atd trltfol rdth€ -

The Pbotl6hine ha. . benzetre aDd DyrtdlD€ lttacldd to

th€ t€ddnst caltDD ol tbe dlrethvl lfopytltt' ne chaln'

thq a -cH q!@P IE FrEPlace'l bt = N grouP? therc l!

!€ry Ilttle ch6ge iD ttE .P€ct!u! €icaFt for ' rliqht ltt€n'1-

ficatid of ttF ld9 r€ve lenstb b"d (forbtdddi -15 ba'd) 'thus ttE spoctro of benzse .nit PlEidlrc a!€ slftLl6!' lberefore

lt 1s not !sp!!61hq tbat th€ 'T tranlltion 1a agarD *s

ln the3e @rqbsd! arosd 260 qn. In tbe 4* of h€te!oci''t€"

ln aiLlj.tloo to tlE baaats itue to F j F.ttelttl6ne' teak baDd'

rlth vlb!€tlonal lttuc'twe (R_tard) due to n* f, ttan'1t16!

.!e obsened .t 10Dse! l|€ve !€ngtb. rlEEe t!'Dtltid5 d!€ to

non-band€d €lections on ttF nltlog€n of pytldhe 13 e:qFctcd +

to b€ Eak .na srosd 2AO-3OO Dm. In ttl{ @lventa' ?ne n+ /\

b.oals 4e lhrlt€al to .toE! $!e l6qth elth IoaB o! llne atluc-

t!!€. rf d+* bantls !r€ verv clos to tbe F-td b'nd!' the

fotur b6nd! @q)l€tely sub Elqe lnto the L6tt€! lD pola! !pl_

vehts. In eciillc lolutlons, thc vlbt'tloll ftte 'truclut€

th€N' ]i b.trd of Pyrldlne 1. dldltristFdr brt th€ Intotrcv

o! tlF baDd I. rtre€€s€d. tht! Is du€ to tlE lnttoductld of

o poaltivo cbar9€ 6t ttE nttlo9€t stoo'

fh6se b6bds c6n !€.dtly bG &d 1! th€ louortnq t'bl€

!-U--U19EDe!e_9sr1f!!1IE&ts€nilost€D' t3 Bn e,at!{'le of th1. c!a33.

'."hls €rE ud €hor8 € btDd at 23O @ due to th€ dl€n€

.b.olFtio ed a b.hd €t longe! sv€ l€nqth 1.€. 6t 260 N. th.lo!9 rave loetb bod t! bat !nt€n* tn tlc cee ol thloph€n€,

Fo!.!blt beclu$ of the lDter6ctid of th€ 14-l,y1nq d{!tbt.tr.the band .t 25a nm lr obsrv6dble !n this @npound brt

!o! the above @mtFud .t 260 I 2 nn ( a E 4r5OO .t F{t .nil l).nd at 2aS .m ln ttF aanF !8d1.,

tDtenslty !a.16. {j,th th6 n6ture ot the bufl€! u.€il. lor

= r (a =6,?00) fo!pH- ? ( € -6,500) 5nd forpH 12)

fo! the .bov€ @mpoud6 €re grvo tn t!bl.4e 91v.n 1n ttE ttgues of the asEndln.2 .nd th€lr st*ctt5

D. ItrFR;,RED SPEgIR,.

si!@ m5t o! ttp ohpourda .r€ iDsluble 1t orq.nlc

&Iv€nt6 thelefole the stFctlE of th€ antlh18taolne. ai€ t.k n

1n x.Br a.d .!€ qlven 1! rlqur6a 'rhe sgslcnFnt o! tb€

Donds hav€ b€€n 91a€n table. 1-14 ol the EPt*nd1t.

the srf,ctla rhd tlE lnt€! plet6ti@E tFve helE€d 1n th€

chalact616atlo. of the coilrosd. Htuvd, t+:e4 h.ve not prd.d

!o tE o! ahy slqriflcet' vllu€ rlth legald to th€ antibllt.nlnlc

33. atirlrls, irudnts ltechanlct1970, p.p.373-3?4.

'TABI/EUltravlol€t sp6ctra o! th€ artlhl&.nhtc alrug8.

r,chrotplHtledn€ :64.4 lor?0o261.t 9,00o261.9 9. tOO261.9 a,aOO

264.O262.0262.0

6,5qo 2A5at loolr 9o0

292.0 1t&n2a5.c t,fuo285.0 a,I0o

214.J 9,20t)

285.6 (.!) 25, 5su

25a.6 23.5u.)

247.2 2l.9rJ254.5 21r6t!254.5 22,5!\)256.9. l9,8JJ

25!.3 31,60.)25J.1 3\),4t.)25v.! 29,6vj

242.J 2J,1r!272.. ,6trrj

?63.6 ld,JJ.)262,! Lt.tt!:)262." 16,5"J

25S." 617,J

255.v 6,4.,.

3.dt!ell@ cthaae

s.DaDb.Dtr DF.Itn€

Dtscusal,o!r(a, 1. AC|ID dlSsoqlAtloli AIiD sl?allJlli @!SAi.\1S Ct

tfl51!ldni6 r\! ttl sli|lgNE-LIKa @upouliDs.

d.t.tabloc .!d colEoqd! !.lat.d to dl5tadln6.

D.iorc d1'd..1!9 tb. .at 9.olrtr ot bt.t d!a, ttr1t1 Fi L dr o! pl!c. h.r. to all.6ra! t!. .trqct'rr..lte.tses? €ctil-b.e Fotlrtl€a, chel€tinq abll,1tt.r .nd th.l,!cd|requare. oo th€ ph.rmlcoloclc€l tfotPrtles ol hllt.nrln -Ilk c4F6uda.

;r1st6mtn. h.. th. .tructr.l fomrlar - '

_ cLrr-C'r:-Nr{:11i\vN

a- (1oln6thyl),,ltlal..tole

It 1. .ttdt D... rlth the pk.! of 9.33 for th. .dt.ogr@p and 5.I3 lo! th. ntllot€n b the 3-Fosltid of llnah-rol€ rtop. at th€ todr p8 tt 15 €:gFcted to b. tr.&'rt hth€ tlaao€! a4 . @noplotd.t.d a!*cte3 folclng . .1r t!tib.!.d

lretal tdr oay alF tl.y .n i4ortant lol€ lry tomrnq

a EtaI clEl.tc rtDa-942'

",1.',1...ilM'.

L.ry colto6d. b.v. b.- ttd€C rhlcb h.rs hl.t.dn -Ilr€ Bctirltt. ..11 o! tlFe c{l'ol|tr& havc th. Lldc *tuct-

\\zc {!- c tl; l\ Hr

rhe qh6t.cr*latlc. o! actle. 6iDd|aar tn €n .rrFo-othyl eroup ortlb to th. Dltro96n of a €Ft1 h.t€!oa!'clt c

!1nq. tbe ts9!h ol th€ .1ib crFln iDIE6!3 to b. elttcrl..irtrolfopyl, adlaotutyl ..il othd sl,.titut€d .dilbo€Ityl

cd9oud5 .r. not actl!. or !€rt !..Dly .ctl!., ttt|mh2'

lound t.hEt 4-(.oin.mrhtl) tnld.zol., 4-(3-!nlro !-butyl)t61d6Fre Er. orly t€€ut sct!v.. lx.bort .nd !.!.to25forr.d thit 4- (adloo n-lotylj htdatale v.. 1nrctiv..

,S-tu'-'''; t"r c 't'- nttl'

4- (.otro !-Layl) ldditaal.ryo!r'- -lso losd tblt I - (ldlrosthyl / i&ld6 @l€ wa tD6ctlv.

l?24, 1936.

J.che6. 3.c.r 2172, LglL.and ti.b€to i., cn d.chea 4n!ra1lr6tt, II

Htr- CH.-cH - ir J

1 - (lrdro.thyr) ioLiLlol€rh€ qqat.n.ry !.lrthyl-.thyr 'GIu 106 Fs abvola ot

l-=Tc",-c\.,-fi<:!H,N\zN "l

a-(Tricthyl .frEtrlor ethyr) hlitllole to.r

3-rietbyr h1.t cl.e 1! .t.o l€.bly aoilv. b.c.!- ol !h.bletlrq o! tlF chel.tlnc .!te.

j- cHa- NhLH N.\ZN - (H3

3-l,bU!'I hl*aelneoth.! $oD.tlc h.t.rocycllc rlnc. c.n b arb.tltut€al tor th.iati| !o1,6 !l!9 nitb only .ught f.u l! .ctlvlly: egJ

$'*'-"*t "*'cilr- ( Hr- NHr

{-{qidno€thyl) thiorole 2-(ndtrorthyl)ptttrah. ,

26.Pi,rlAnrt.tJ., .t.cb.n. rb.,, 1d6, 1915.

'10-5'terlc ltlDd..!@ 6I$

trE ..ttilty. thr3 lt 2-ph.rUl

vcly le€bly .ct1ve:?

,-J(|1.-c '1:-

HN...lPh

2-pbcnyr hirt.Dina

2+rhyl hlat.dF

sidrsly thera .te lb.t o! .a'qtls' i'blch tltov'

th6t h1st.drne-llt€ .ctLclty i3 coD.ider.bl6 dll' vlE 'rt* reoberod cb€tlt€ rtns catr !E tolttt€at rhtcb includ€6 E at

of . heteloctrcuc rtrg 6y!to6 th6!€by bflnq1ng th€ h'teE_

ctcllc eil tbe chct.te rtnqa tn tit€ .sG Plhe tbich olvlo_

.Iy provlil€s at.bitlty to the av.t6.lqulr.icd npl4 ratlos (letltlv€ to ht!!6alne : l)

fo! soc lq)ort nt 6..roqEs of hlst'dn€ 4o h'tac clv'!

ln th. t.bt€ Nor 3.

lbe 6qu1!tt.6t 6lar lstlos ue only loulh 6stiate

made !y bloatEay ol €ffects of hlstsnine @ the clt blood

pr€6.ur6 or the quine6dq rntecthe'Fros the above t.LIe it !s dl"ent th6! ttF €qtrlrF

ot6t rstlo dsPnd on ts f.ctor.r-l) ct*Ic hlnd!.!e to chal't€ fordEtld'

2) Acld-b.& troFertl€3 of t'F !1n9 6ltBn'

tb o!d€! to u.d€Est€nd the 'cld-!'}a6€ PtoiFltlea'ltn6y be tn.tluct1v€ to esnln€ ttr€ Prcpdt1€' o! lthvl4€

itlBnine, propyl6n€ dj.aFtie .ad soG o! their de!tv'tlv€!'

2?. L€e n.H.J lnit Jonesr R.G., J.PhsnB@l" 95, ?1' 1949'

InELA NO. 3

.n.Lo9ue. o! nl.tlGlrE .rd tb€lr aqt.tpotent DIE !.tlo.t.'|.R.

i--il\tiN -Jeqr-c fii R

stsrtc tactot (29)

(n6t€!tc Fctor .rd

rj,N']l*r{

lld _-_-:r- cd r_ c|{:- Ft Rr

,t-l\lll|--l.cqr-cr{r- N{:

isrLi_ri/-c'r!-c+'r-

7d1cr.,-c.r.-.rn,\,r" 20 - 50

Z\{Hr-c{! NHr

6.1 at.ftc !.ctoa (?g)

r€au€d b..lcrty (')ol tb€ Elll .l'.tdn

i,lt.rn t€ .!t€ ( ')

5oo (.)

(\cn.-.*.-,.r1.-N/ 5?0

The @1€6!le ot Nst64lne 3trd h1.l6b!n€ llk€ coqF

osd. rn y be @nltd€red to be the atetlv.tlve5 ol tlolvla€

\{r , e|.\>'c\la c\{!. s'\H)

r,3-dlantoo laoFleln h16tsfrlne, the llrst dsbon o! ptolrylete

'11!-mlne 6nd it. Nltroqen lorh Flt or lhe h€t€looi'cuc !ltg'

slde-chltn r6taiDtog the Btc' tb€ €q[l9ot6t

!et1o 15 &iFod€nt on thc chelttlng rrltroc4 of tbe rl!9

Eysten. val@d for the .ctd "Isbciallo

dst6nt' tnd -r€

o! tlre !e1d6t c.Ntpo6d6 ls givan It ttE teble !io' 4'

aron tho at v. t'ble i! drn b6 se6 that ottF'

thtngB b€tns €quar. h!6tamln€ lik€ actjvltv lB ooLv rlls bl'

corpo6d. of ihlcb the rlnF nltlogo !s f!€e !!on sterlc

hlndt3le aDd stbse pke iE 5'o or ebove' all thot' 6'19_

oqd! ehos pks 16 leEs ths 6'0 sbor ' reduc'd 6ct1vliv'

This can alBo b€ clt€rhately Bt'ted ln teln8 'f 'lectlonlc

charge o! the rltlogen of tbe rlns @nc!r€d'^. t1' q -. 't-t

(:"..,

-f'"ldl-:.i""

'Ih€ .bov€ trc ale Pl_€relalr€ hel€roaronFtrc

riDe6 nth a hloh n6(rsttve ch'!g€ on the hetelo 'tom' the

r.ow !ct1v1ty of Ps!6I!eI !y5t4s 1! du€ to tt' dellc1€Dt

het€lollontstlc rtngs ,1th '!rP6!at1ve1y

lora! ctlarg€ o!

th€ ditfogen!!

,ll,tn\ll<\\*/

?'l\,.1(\'\i{,'r'

tiBLT TO..r.ctil Dl.'oal.ttql qtt stt of G.tt!t! t r.t a ala'lttat

lrt2. Ca!. cCa. lil2Irh. aSi. cs3. E

9.Arr7.2tlo.t4rl.ll -

a- (.rlbo.thlll llla.t 13

a- (1' !atb.{ .thYt.rb..} tda'._{- (.d.o!.t!Yu tbr.l.r€,- tad.a.rlir) tbt..ol2-(a t-6d(ro otbylrtryrtdl@

i- (aurao etl|i r') iftrcm4- (acrro €thYI) Pyllii'ar!€

t,8t9.15

a.3t9.4?

9.tl9.69.66

a.lla,94

l.ta2.o'

r r.t&attd v.I{...

r)fi-)

11t St.billty 6n6t6hts o! th€ metEl .hel6t t ot 18t.nrns lnd

1l1.t€rn1D€-Iile @npou.d6.

Etcept lor El.tstane .Dd rdstldl.e, ilata 1. not avdl'ble

to! otha! .naloquo. o. agoni.t. of d1.t66he. tn. folldtti gta..

Th. b€!! xnoh @Drt.{t6 o! sor o! tlF& codPosd6.'re glv.n ru tb€

t.bl,e No.5 s paq€ ro,

It 'tlt ba obtervad !.oF the table No. 5 tbct qhcl't1oo

o! th€ blstanlnlc cdPosds {Ith th€ cu*' 15 ploblblY conDectod

1n 6dF tllnne! alth th€ acttvltv of tbese 6qDu!d6' th€ strbllltv

6nst6nts of th€ chel.t€. of cu'r id 1s roughlv ' tundtid ol tL

potency ot tlF& mled.Let. lt<)udq, tlE dar61s t@ Gaoar to

jultlfy such . rt.tcent u!€quivoc'11v' r' the oPlnion ot th€

authot, tll.tsdle rem1n6 .ocho!€d to elt'in sltet eltiln ttF

dst cel,Ie qhl.h lt sto!@Btf,clfic ard rhlch 6n!cin' a Et'I

ioD, rc.t PEob6btv qr+n tot ct't: tttot' thjB hltbtheE15 riLl h'v6

the fo1141tr9 6n6€qu€ne6:-

Allelglc nanltistntlon v1lf t6ye pllc€ vhd 6 fo'ellD

protl€n, p!ot!€n-l1].@ Fubstan'€s or ! Nch Etronqer ch€l'ttnq

ecent ca di.pllce tbo higtanine lron it6 61te' th€ dlaence9€d

htst6nlne ilafues to the surlosdlbg tis6uet snd dl(uPtt tb€

sffiro!ftl functton lesultlnq in urt!car1a'ha@!!5gc 6nd dtt_

lactlon o! ve!6e1s etc. th1! $tv evqtqallt trigge! th€ ttudr_

atto of th€ .y4patb€ttc neEvou. svtt€n'

rle€ hi.ltadn€ {l1I €v€ntuallt b€ deattov6d bv 'nl

ox1da.e6 j,! not prosant ln l.ree qu'nt1t1e3'

Antiht6t'olntc d!u9r c th€ ani'gonl stq6' ht6tt8!D€

ato{rld .l.o b. chel.tlDt .96ntg of lbout equrl o' l'!*t ch'l'tlng

sb11lty bot ot t!o!. lPlctftc n.tu!. tlth r'9'!d to dht t'q)lal o!

tb..tt d(.d t1&u.B e.t to ill.Pra€ lhe ht'tAdn' G Protect

th€ t!.!ue €it.. bt cov.!t!l tIn ld&ly' rtrl6 tllr 1e've tt.

hl.tltdtre tr.. t b€ &tt!o!6d bv 4zvB! t'rch a! 'dDe otl'F ta

4. Th€ .nti.h1rt.D1nic dsgt be 'ble to P€a't!lt' (l)

th6 tbold t1tse5 o! r!$G'n 5 'bd {ii) 'h!no gtooP thoulil b'

protcct€d !!oE qut ct d..t!uc!t6 lry the 64'rss tuch !s hltt'4l'-

.4 0t oth€! .ndne ondst.r. 'rhlt 1' erttlv 'bnc

lt| &bttltutl'g

th€ te!d!n.l _NH2 trouP *lth 'lRt)l€ '1hyl

groq'! to qtv€ tlt€

- !.: soup.'i

' !. iciD DlssocrAlror coNsrlrls /$'D sraBrt't$r colsr'ttrg ol /i!trr-

rcsllllxtc D8!'CS.

Ih€ .ntihid'nnnic 'foupt

!'l1 into th' forlorlnt 'EooP'

b.!€d o! thet! ttluctu'r f€'trE€r

1. S{lbatltut€d Etbyterc Dlanltre!

a'. .,--)x _ or, or, - u iolst 2

ldlE!€ & tt tn llotFtic llic and i rt ! b6nty1 9tooP ot

tt! a!.lofu€.' e9.

' cu".-fl -' t.'...,",,,.o.,.,- \-'l Z'*", IrFtryraur.€ (,.!ir!l6r'ri) \./t2. DlPe$ttrtne 'n'tolct

ot €ttryl6ne dlaElne!'

O;iC-'*

Tt -16-

It ls c5l1€d .h q..lo9ue of €tlryl€!€ iulalb€ .. tho

Fllfrazln€ tidg \tnab! 41t.bt€ ondltlo oP€6 ut, to qlvs N_N'

sut'rtltqt€d €thyl€D€ dl,.tn1r6. on tlnq oi,@I||c, the .Dov€ .y.tdhay b€ !€9r€.4t6d ..!

ctlr. _o)'r.(

Ph€botlu6atre det1l.tlvc!.

]. tupic.I 6x.q,t€ ot luch a drus t! Chlolc!'cUtine !€F

!3s.!td b!' th€.bove torErl. dur x ' cl ln tl€ tF4 t dtloll'3. Dl€rLyl adno.lktr ld.r.

l.l(:tl-o-(l.-cH,-d(cs3)2a.

&h.t€ R ' Ph€nyt o! t!.loDtEbvt tEouF 'ad !t r Ph'ovl or

2-p1F.lttYI gforrD.

A q'Plcll oFq)}e 1a

%tu>o -o -cH2 -."r2 -x (c'a)2csH5

)o - o, - cri2 -r(cs3) 2

Dlpt6hYdt.ils (BENAticL)

Not€r i!€te tn dtl.tlDg lvste! t, dtlf.lst lFo ttl $rtt&n'dt6nlno t!tp€. It ls throuqh o:99€n .hd dltlol€t'

rtpre R ffiy be s1q)l€ !1kvl r.dtcal. o! c!'cUc or

sltur6t€d !1nq.. r ls qluallt rryiLog€n bt lD aod6

h3loa@ 1. lub.tltutGd .gl

. EroBthszin. (PlEdrRotN, Alorctra)

5. l|n.loc@s o! Ph€nothl.ltE. Itr.€.bor,. ercept thlt on€ of ti'. bar.n€ rlnc! 1D

!y6i.o 1. rqt c.d bt' s ltrtdbe rbcr

d|.e lneludc. alltl.da.t, lroPyl-Azllluoc€n€ d.r1v!tiv€6. aroryn. o! 6b

6. xl.ell.!Es!..4!.3, carblnol6dn€g and

lllyl.dn 15 91vs t€lorr

<\lttllI n - c*- jc

-cz\"/LJ 'T\trlDroltdlne ,r-r-u, v

tlpl@l tro{rylanln€ rntlhl.tsnln. t5.

Q-o.-c,.2-cs2-u (cB3)2

Ph@lrrnt.o {t!rrtd!)It r1Ll be obt wed tlos trF &locture tttp. ot th€

.htihl.t.6thlc ilruq! tbot th€le !!€ t{o @d!m fe.tulca {rlte!€!€rnbl.tnc tbe htrt.4ine 6nd ht.l.nl.e-lite dqFud.l

l) tb6 sL& cl|.ln ,,. rDv.s''.btv .h ethvl.!. dl.rlD6

rbl.tr. Tb telolDAl aolno qloup 1! elravB lqut .11q1't€'l to

91v€ . t€rtldy nltlol€n.

2) 1be !!ns Ey6t€n caD t.k€ a vallety of folnB. th6ae .re g€rr-

6ra1.Ly lerger lD €lfectlve 614 rh!! th€ 6G.Ll !1n9 .tat4a othiat.nin€r, sore of tlE r1o9 systehs a!6 the sac o! .1E11!r to

the dru93 ued !a entlol n€rvoua atstem delae..dntstpbaottfar-l.ea are E1l l.ooM tn th16 @nn€.tlon.

Ir v1€r o! the hypoth€516 o! a$urptlo. about uFactl,@ of tlreae drugB that have b€en etven ed11er, &tu dluqa

beve beeD €).adn€d for thel! actd dis6ocletl,on con6t.nta add

retll ch€lari4 st bj.lity 6nstanta.Chote of tbe doqal

A6 many lep.esehtetlve dEug. rer€ chos€n a6 eer€ aval.L-

ab.te flom the diqfacturers. the folforhg itu96 kr€ €Fa1D€dl

l. subetltuted Ethylenedlaol,ne:-c)ct!el!e, cblorcycuzin€,htabllner Anthiaanr ,rtelqad, a 1571.

2. Dtalkyl amlno .lkyl EtherEr-Benedryl . drtbdryl.

Ph€ne.rmlne r chloQh€nersotn€.

Dlethazlne?Phel6rgaD.

The {€Il €6tab11shed BJ€llumB pot€ntiomtric rethod tortlE 4aluEtlon ot acld d16&cletion and stabltity co.staDt. Frecho*n. ttor4e!, tbele rlrc llnitations on @ltaln ct.l 1dato th€ tD6oLubilltv of the conrplee6. th such caEs, .atinateshave b€e. G& flon the talue of the t)H at ehlch plecipitatloo

Spectlar e .tt€rFt h66 lEen rrr.& to obtaln U.V.!

vtolble aod Int!.E€d stFctla of th€ lFrent corqbsd6 ond ttFi!@ta] chelat66. It has al6o been .ttemDted to study 6c1d-b.&

ch6!act€! th v.r1ou8 8olvetrtB ard buff€lB. lhts *a5 tlione 1D th€

hole o! obulnhs e,.tra 41d€ne.

!&-!9!e!9!!!r!;ll tlr varueB obtalnd 1n tb1! bEx and tucludilc trbe

rhlch .!e .lr€ady lgtorn !! pr€vlous sorx 4e belns tr.*Dt€d lnth€ table6 tha! fouds.

i:!iEF TF

! 8-!,!TSfoX"i'Fox

E50'Et.€ 35iaE

:Fii'o;4!Y!cS744

.sESiEY

E!ts8 g

r.1 .t

8.:8Ft

3..E!.9ri.?E|,8

Err!E6Bo

-:! -n q

n" '. Io.8 !o \!z L

3?:!IlirsFTi

.i388dStt

itI lii; 5 F:f r€r,b iJ!

-:.0 : ilI iii- eEi.ttt

E<lstE,vEo-.:E

[t!tIt

at!$E8

qnla?l

r& lE;;'"Yr.e. o.4.8 ii.

IrltJI

n n5c&L

j'c!i3

I t9EI ;{rl 3l"t 88r., Eo.g

i!19gFEAU

cohc!uslon

It 1r €v1d6nt fror the folegolns table! 1 - a lDd th€

tabl€r 5 - 9 that th6 acld it1!6ociBtld @nBt.nts of tbe torftln-.ls -N(R2) of anlno€thyl chat! o! both tlE hilta4ln€ €hd antlhia-

e!€ o! 1,6.. 81m11.!. The !il(l v6luer lte l,! ttE raDg€

of 3 to 10. M!jo!I!y o! the 6mpoed6 have a valu€ near 9.5. Thltia 6 coEe f6atre or tlF a9@1st6 5nd lnrasdlst! ot blrtastneand ho. Dob€Bdnc oD the €quilbteDt Dra! !.tto o! these d.ui..tn trE dl)Itriotr of th6 .utio! ltoDty €q,rr€61*s the badc chlractorof th€ attacklDg rc1e.u1€6 o! rhlch the 4bst!.r€s lrc .ctitlc j,n

cb6t!cte!. Ihe pk2 vlrues (fel.tlnq to the ottEs rllrloc€n tn th€ch.1o or the lihs sylt€h) horeve ab Bhor @F reanr,hgful dltf.!_4c€5. -\a .tated €a.116!, rth th€ t61.1 tn ptg v.ru€6, tb6 €qdr_ot6t rcrar !st1o of hlstamine-lile oonposdt i!cr€!*5 soErbltprol)otlaately. rt 1a aot posslbl€ to le1ate tbe Fig v.r@s aaat

E!,lR valu66 ln ant 6tmpte nEe€r bec.use of othe! l,r!r.t!rt factorssuch .€ lteric f6cto.5 aDd @ta.L ch€tqtto, lnvorvod. The ptgv.lue3 ot the aDtlhl6tlninlc dlugs 116 gene!.lry tn the r.nqe of5.5 to 6.5 rbicb 1s lder tb.n tbe ,tr@9€r hi,stadntc d!u96 aldhleh€r than the f€€bty acr1v6 dluqs.

llE atal'lllty 6nst6ats ot !€++. co++ , ?jn .nd t6r++rlth both th€ c16!s€s of conFounds ale udifolsl, srnil.r. rt Lsd.ty th€ los x v.tq€6 -r the chetlt€s of 6pF! (or++) that .hoe@D.1de!.btt ch6d96.. the histadn€a haee fo! !h€1! loc R vatqesfo! ctr++ 1y1n9 b€tho 9.5 a.d 6.5. thoa 6n!or^d6 havhc 1ftrvqlu€e a.e les€ act!v6. slstAmine tt!€tf na! !,!ru€ ove! 9,5.the lot K v.le6 for ttF chel6t€! of c!++ rlth the 6t1hj.st..htcdtus. 1€ co.lldelsbly lo{eland tatt. j.n tns rans€ oa 3.5 to 4.5rEre .te vely t4 6!po@ds rh.t t.11 out!1ite thrs !..9e.itot bt€ .egtion behg N.N_ dlmthyl N_ph4rl ethyls€ dtanrn€

(! 116?) rhlch of-coulEe 1! v€ry veakly actlle. the diamlro!1Jqrl

ethers tlle 6 dlffelst ch€t.tlhg .y6t4 rnlch 1s n6d6 up o!

-o- cn2 - cll2 - { ayEt€m bot lnq)It€ of th16? tbe Iog x v.l,Eaof th€6e @qrsds !o! ttE c!'+ 1s 3ti11 Dot v€ry iUflerent fro!th€ ayat@ rcite on the ett!'te.edl.rdne 6tateo. lhis suqsoatr

tblt one of tlE 6nclb!1nq lolnt8 ln tlp substrate 13 prob.bly

@ppe! xhlch i6 Feseht ln ths ry6ten eltber th de enzt@ o!coq)leEd rlth p.ot1€! @l€@ler. Tb€ aDtlblstanlDlc dlugr p!o!-id€ s loo8€ bondlhq !t thod6 polnt. ,hlchiE r66Uy aid6d by th€

bulky .-rd group8. The.6 .nd qroups a.e t!'pically tr! alotnltlc

ltnp Eyste@ on elthe! 31de o! the cb.!n Ts phenyl sloupr. s

ptFnyl .nd 6 prttttyl or €v€n !,lenothladne have eirlt.! orl€nt.t-

- q-{ j Fr (q{):

R.a-Earl@.' claths ttr6t .tho aogula! dtslbs1t1oD ol the ltng

F-Jletr 4bo.$ N-s axig

i i'. rAr-.l

33. Blrlov R.8., .nd xhan 1.; Bali:J.ph.rd@I, 14,99,1959.

r! .hort, ttF bbdtng r|!d h€46 th. dcllvity ol tl€t€Dt€ol.. irvolvc! all, tt'tF. ot lBd1ag!

I. Ioal.2. covBl,€lt ald @d1n.te3, iln itier $rlt..It j.. dIlilcult to6i€Fr.to the eltect o! oh6 troF otha!,

blt tlr.r€ 1. rc iloubt thrt oootrtitlve etEl cb6l,.tto[ .nd .nqrl-€81a9 l. th. Fir blor{racat r6!ct1@ tnvo&cil ln th€ .cttool th... dnrc.. rbrcv*, lt l. aoe$aly to aqb.t.dtllte th.r.aerult! thlough atudlG. h vtvo and c.try tlr€ rrot|( throqgh trlt !d-cotoglc.I @thod.. rt i. Dot to .ay that phalil.cologtc6l

'o!h ht.not b€€n ibn6 1n ooD!€ctlo r{ltb lllergy aDd lr.ocllt€d ph4o.enon., A!. tr tt* ol t.ct. 1e9€ voIle o! rcrk h6. b..n &d€a.d i. rtul beltrq el!1€d o, bot trE Hhole rtt€.. .o t.r ha3

b€€n oo th. lqr@to9lcal .hd th€ t€q,!at€s fltr ot Dlecrl€3.1t tDt ln(b.d !@re qult€ &uttfur lnd lerglittns 1! ttr€ iur.ctl6o! th€ (b.lgn ot th6 E&q!n colotlcal t€BtB 6!€ cbarg€it ln vierol tho !.rr olclualdra i||ar.t| !!om thta so!k.

!lt. sul{6RY

i, ry.t€Fttc €Eatn.t1d of t!€ €qui,ttbrl. ol.nitht.toetnlc dru9. lnd th€ts ret.l ch€l.t€s tn aq@{rEill@ b.r b€sr rab.

4Id alt.&cl.tloo dl.tADts o! .ottldrtlDta€g h3v3

D€G.r d.t.!!1Ded I'y !.t6lttoBtrlc tttfotion.stetFrle ltrD4urt coltlters ol the cbelet€6 ot

cu (lr), rt (tr), co (tr), r€ (tt) anal ,i (tt) of 6!ti-hl.tanb€. lave b€.n aaluat€d by u4 of rj€lrMr3 !o!_

ul,tr4l,ol€t .nit tntuc!€d 6lEctr6 of tho.€ @rFound.hse .I.o tEe &t€ldh€d ln the vE.t@s dto.

ar-l--l---!-!--.P--J---!

D€rlv.tloo of lquqtloo. u.ed.

r. stabtuty co!5t nt.!

rn - d!+ + xrtr - R r , r|lir + ,ia*-- (r)

srtB (2lr. + kt)

i,a ablcrlb€d s.rltct 1n sctldrvB , r.€ c{rn y.!t6

lu . r++ +&s++. MnlCl_ - 2l|i+tEoH.+cl-.nt-ri.*-znrl'*nr. z*i + 2 rar€ + zn+

subltttutlns (2) 6nd (3) 6 .qu3tl,a (4) .ad

cr_ - u+ ttg'. z RB}" + !!+ret s rqtr .€!ta th€ r34ra.ibl6 q!.ntlttt

theletole, s = & l4'2/ kr a2 + a+^zt

le.rlanFlng R -

-___ (z)

-'-- (r)

---- (.)

6 - lR- Ek't r'2'g-tr ' rrrzt

Ptoo €Suatlo (r) rb.e€ h a.

$R'++2drt = te- ra;+ - Rd'- R

=rn- r tu221x2 +f^2+r)srlco i = (sR" + 2t.lr")/rL

rn-rftr'z^rr2+Ei, *2+rl

(r) 6r; =

loi (tir \2) lnill.rw.oil t.5 or.3aDdd

M+* ;lia+, * MR*

Ot111zt!9 tho d€rlr1t16s o! kt lrd ltz

xlR + xt82 -2

- dRn + 2||d1'

I'xli+xlk2n.

R = 6_-1)ri1 I (x12

R (1i)

;-+ tr R(n - l)

l+r,2R

.... (r/

.... (21

.... (3,

,.... (41

Kt& (2-ri

sut'6titut1n9 fi g 0.5 1r €quatl@ (I) r|G tFt

I + Ii2R

1*(1 +-+ le k2 \1.-q-'tlFtr I, t-b6n xe R-- o

equatld (4, q1v€!.

x, -1 on roc ri, =

at r-l.wi €.rlDtlo.r (1)

r*,r,r* - I tl-N XIR

.{tstituth{. tte v.!ue ot;i.& at ; . r.5,fld €.ru.t1otr (1,) r get.

(t-6) 2,

12x,^---!----)'

L2to redue equatlon {5,

!!E!les8€REt

s.,iill, i;r31" rs.lllKo, r. clFnl.ch€! z€nt.6r Dlatt?

,llDRl]|a? ,t.C. end Klali &;tisr,y, J.r J. Cl@. soc.405,t964.ilDlrtia, A.c. LyO!/S tltD orBlaat.J.chon.soc.r 2.t?76.

;lilli;"ii;"1'?liili:3guaDtu Lech.Drc" crsredon p!€!!,

*ffli,i;";.j.3jfi*ffiT.i3o1**'prro'ftcobo,6r.Rl,orirR.g. .nd \r!,ti, r. E!tt. J.phslirscot,r{, 99,1959.

I#:i";.f '$"*g:"i'ffi i1*'*'-' ""^...""'Crt.Rlals, R.c. ph.D. the.le! ttDte€lllty o! pi tt6Lorgh, t952.va& uIr&,g!. rr.c. .!ld I$ss.c,o., .r.:@!.cEm. soc.75,45t,195a.DRitstR, H, plutelE. ,rch.ge. lhys1ol. 76, 306,1a99.

i:j1ii;"i!r!Y*'. E., rltcrtn('s. c.r. J.@r.ch€F. sbc.

qlt., ron. ch6l'l. Fh.!n. r5or9,lA59.fiIPEiN, B.N.! ?,!cb. rbt€h.,tEh|a6d!hat1c, 6A,339,1942.

3f *ii; "li;i 3!ill"i"lf - .'d s.rorz, c.R. .'.,e!.ch€n.J;-Ct sdn BlRfr sc.j&er. 4ot 214? 1966.\rr\rN, }{. 6rd tt!(br. (,L.J.dEr.Cb.soc.67,2003.1945.r,E!, H.!i. ahd JoNls, R.c. J.phlrFool 95,7Lttg4g.LEE, l|.!i. olrd JoNrs, R,o. J.Fh6!&acol. 5{, 265? 1935.,J#:J!.;j::":l!ff

: L.c. rstablllty constants, rh€

i3il*,$1. ?.liu "l:E$:il:'":r"f i:1"3!".i:;:,,,.NMLIrd,c.6ad tl..Is, J.1..r..er.ch€n.soc. 64,22da?t9a2.

al. tatos,ltD.r", ?t *aot. btr. 9, e69,t957.ZZ. 9ua,l.t.!. t.ct-.$c., 2tt?,lgtl.23. Ehlt,tt!. it.ch.n.sbc., 186, t9l6-34. ratD,J.r lg,rlbi,t.D. Brtt. lrrar. t, 2,!?!. t95r.25. II!a& t.r.r ldb.!r{.. 19,..196!,,25. $Cra, c. Doctecl d1!r.$ara. €(!t ltllv. 1960

27. :!r!9!{rr!t 6so.DtoFrr$.. }u.r.r.,r..d.ad.60, rat. 1954.

24, ou(|r|i, o., B,tsFt, J.!. !r{ Be!i.,D!C.t. 90c, Eol8611., tza,44t, ttSt-

laB!t I

cb.I.t loar.tldr Dri! !o! D$dlyl tcl .od fl (tt)

tltltt.Entt s.c|c!.D ld nt ! r6drt (3lri - l.za! x lo_l tbL..tx . o.a?5 r lo-3 DL..coc. of &q - 0.096 Ietgt .l VotrD . lO5 nl!Dq..|tu!€ r 25!O.loC

0.1637

0.3196

o.a9a7

o.66t2

o.a?45

0. ta92

1.t565

t.tar2l. {{}73

1.5505

r.9607

tra.rE8a

a.0t06

3.9430

3.Jl1a

l.a5ao

3.?600

3.6561

4.6091

3.604?

3.1952

3. i80?

qr6.?5

atr$&iut d rdth Dech.! at.!d.d lult r a.o! rd

tABLt II

Chelat. ttoleat!@ I).t! rrbr E r.ibyl lrcr ..d !t(tt)

B.clb.n qr tt r Da.1 slr1.642 t 1o_l ELa.o.a r to-3 DL..

c60c. ol h06 - o.Oa26l ,,oatg!.nll volrllr. lO5 nt.reqb!.t|e - ,5io.loc..

volrc ol L6at !n.o.1

o.4(L5

7.€a

€-00

0.1637

0.!383

o.looo

o.6611

0.8335

0.e040

1.lotla

1.1944

1.5218

1.80?!

1.9607

h5.tt9I{.9015

a.6aql

4.52art

4.4213

4.3270

4.2606

4.19t1

4.14?A

4.110?

A, gt€ldAldl4d a. 1n

PLd'l.dF scl .Dd !d. (II)OEl.t€ tq!.tle D.ir !o!Io.t:u!ea!tIi'Il|co!c. ol r|.(A

. Orl,gln l Vol|rD

I€rq'.l.tul.

Vole oa rFoI, d,

o.t0,:

o.7' o.a

s.clo.o th Dt€r Edal qrl.?15 r. lo_l DI€s.0.{76 : 1o_l 61G..O,0A26t 'lo5 ,!l .z: 1 o.toc.

o. t6ao

o.329t

0.49,45

0.4611

0.&ta9

o.99!7

t.l516r.32r4

1,4tilr1.49tt

&5.tt675.1696

5.9924

5.9529

5.9493

5.96E|

5.9653

5.9,159

5,9393

.. 6t.ldlltl..d .. 1a

IAELT w

coloco?tcrr-r rcr &d !! (It)LolE!.! Ib Dt r ldl €'.1.521 r lo-3 Db.,O.rt?6 r lo-l EL..0'0936 d.lo5 dt .

25 ! o.toi .

corclot f.oal

h!,€o5.&t

3.€A

o.t6ao

0.3299

o.4ra5

o.6llro.ata9

o.991?

1.1596

1.321{

1.4all1

l.a9?3

h6.r{496.0371

6.tltt6,loo2

6.O9t5

5.10?9

6.tta66.!244

6.1!€l)

1! trDL I.

TA6ITE wlI

llrrEoltill!. lc:r .!d 11 (II)- r€ctd.! h bt ! it,d.r aC'. t.rlos r loJ rDle.'- 0.l?6 : lon Dr€!'- 0.0426 !r

- 25 ! o.loc '

cb.lat totEtLo !tlt! !b!Ilrit!!ql'r.t

conc. o! laog

t!t.t eollGl-qrlrtuE

$olurF o! NaoH, cl

'.O1,2

0.1639

o.329€

0.49a7

0.6632

o.8270

0.9495

l.l!t551.3214

1.4473

1.6551

h6.9a20

6.4691

6,7111

6.6a62

6.6306

6.5570

6.4476.4?7t

5.i,642

5.3366

6.1759

., st.lilllilll.d .r 1!

clEht torlEtlcr Lt.Ilt.t!{rD.tt-_ta

oacr ot h(glotd vo&-!.q:!!tur!

Voilnb o! -dt, nlo.l

o.!o,a

IAALT lr

tot tlt!rol!r!, rl ltrd tt (tt)- E clD. tlt Dt ! Ddol oa'.- !.5?? x lo-l rob... 0.4?6 . loj Dl!r.

- 2! 1 o..loc.

EI5.20

a.ot4.20

8.al€. t6

t*i'.aoto 0,2a3?

5.1156 o.a{t25.2231 o.!5?95.OEa0 0.716?4.9n93 0.is?9a.aa?t l.o5o24.7990 l.ltez4.55it6 !.3555a.{605 1.5159

1.3a4? !.6639

.. at&ibr{t!.d la trDl€ t.

cr5t.t rolrlatt@ !|lt! ror th. ltalr! el .dt trt (tt)b.t lDat - rbch.! h rt ! d.l cd'

lllL! x

.010626 t.t 105 rtrt.

- 25 1 o.loc

cnct ot FoBtot.l voluEt rFl6tur.

vot{D of |.!dr, d

l.a?g r loi rol..0.476 r lon lot r.

!,1o.2

6.lo6.tl6.34

&s.95.:t6

5rAO02

5.?Oao

. 5.55aa

5.a?55

5.378€

5,:ta65.2L32

{.tD?1

4.9034

a.7t5s

0.1639

0.3294

o.aga?

0.6632

0.4270

0,9899

1.1565

l.32llt.1t67a

t-6!t6l

t. 9639

.. !tt.!d.t.itl!.€ .. 1, t.bl. I

Itt&l atoc rllo.|ttr Ecr d oo (tl)

- i.c!aE, rh -t r D.'.r Gr.- l.2al r lq'l Fr.... o.at6 r lo-t 6L... o.n€:16 f.

. 25 I o.loc.

o! r.rai, rlo.lq.?

l.a1.5

0.0536

0.1205

0.2llt5o.!l5a0.4:35

0.5t3€

0.670t

o,72U,

o.7r2L

o.tlgl1.:O59

l.lo!2.6552

3.913t

3.tt6!9.4590

3.36t!

3.!rt{3.aa3t

!.tan3.t9tgt.2t?53Jl3t3.OrUl

a.o!r&l

?.lo7.22

?.t37.4

7.tl?.90

.. ltral.liltia .r tr t lL l.

loE-tlo lt t roa

Lr.ilrtl Ecl ed @ (t).- isb h rttr Dihl 6... 1.6i2 x to{ 6Lr.- 9.4?6 i lo-3 bt ..

- 35 ! o.lac.

o.lo.2

o.t0.4

7.*?.a0

?.6r7,1a

t.a01.4

o.\a?lo.a9a7

o.lalt0.57t2

o.?ao!

0.Ea17

lioa9a

lr 2005

t.5il61

l.6tg3

h!.o,rta

a.tt6!4.5gla

a.1l59l

a.aot2

4.3311

4.1800

4.Zrll9

4.264,

a.25!6

cbllt tbar.tle D.trI!atsu'l.tT.

ru6!c. ot Darstll EleTqnF!du;

volte ot 5q, rl

toc tbdtdD &l Ed oo (tt)- !.ib.! rb -t r Dabl C8r

. r."?15 x to_3 'oL€.. O.a?6 r tO4 FbE.

. 0.0926 ! .

- 25 1 o.loc.

!.973.€9

'R5.7665

5.7905

a.1a25

7.7915

5.6925

5.6t90

5.6919

5.69€!l

5.?20a

5.?Al5.7190

O,l6,alt

0.3299

0.4945

o.a6l1

o.€aa9

o.9t!7

1"1586

t.t2lal.,l6illr.{973

t.6lil5

.. abrihlillr.d .l lD t bL t.

TAELE tclv

for aBato9brtttr&. ncr ..d co

- B.cIb.! th ut ! tEd€I csr.. 1.521 i lo_3 FL... O.a?6 x lO_3 m1...r or0a26 {.

- 25 ! o.!oc

chelat torftto! Data

t!.tirBot

Concr o! !@H

rot.l volqitlnlFrltua.

vol{D of daaa, d

o.lo.2

o.16ao

0.3299

o.a9a5

o.66tt0.0t49

0.991?

l. 1586

i,3214

1.443!

r,4973

1.6536

a.92lO

a.9070

.a.9til6

5.0210

5.Oill4

5,Oaa2

5.0540

4,0226

5.0?88

5.1543

cb.lattt ,!Er.tlo Dct t E

la.!rlrEDi1l'lx'cora, ol F(toddlr!{volo -lt|*rr.tul€

crrrddootaud,E all .!d9.cba Er Er.! |Eiblr.2ta r io{ 6li!i014?6 x 1o-l ddl,.rl0.c6l6 lrrlO5 rt:15 t o.tt:

ilal!a

or,a9ta

Ora259

l.OOO0

lr3.al6

t,6!97a.0q)0

2.!!at?.5?!a

5r 9tea

t.?tt4l.a{ar5.tal25.5rt0D

!.5lta5,3t06

t.866.JO

6.to4.33

a.4i4.6

tt.tdunlr.a u ln

,ttlgt

t|l& r.

t tlo It h!

o.!o.a.

t.o' t.zl.a

DtF- tF.llr l}ord- tscle &,Dt r F{.Ia l.{!tg x lo{ tDLr.. 0,|?6 x lO-3 -1...

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