170
CHAPTER - 5
INFRARED SPECTROSCOPIC STUDIES OF BINARY LIQUID MIXTURES
5.1 GENERAL :
Infrared spectroscopy in one of the most widely used tools for the
detection of functional groups in pure compounds and mixtures and compound
comparison. The spectrum is obtained in minutes using a few mg of the
compound which can also be recorded. Hydrogen bonding is of central
importance in the molecule science for both practical and theoretical reasons
[1-5]. Infrared spectroscopy is the leading method for identification of hydrogen
bonds [6].
The important use of FTIR spectroscopy is to determine the structure of
the compound. We know that any two compounds have not exactly the same
absorption peaks. Therefore FTIR spectra can be used as finger prints to identify
unknown compounds. FTIR spectroscopy in often used to follow the progress of
chemical the kinetics of various chemical reactions. These applications are based
on the fact that the most chemical reactions involve changes in the functional
groups. FTIR spectroscopy distinguishes between inter and intra molecular
hydrogen bonding. Free-OH group appears at (3600 to 3650 ) while
hydrogen bonded alcohols appear at lower frequency ( 3200 to 3500 )
The infrared region constitutes three parts: 1) Near infrared - The near-
infrared is approximately 1400-4000 cm-1
(2.5 – 0.8 μm). As there is less
absorption of organic molecules in this range, it is of little use for spectroscopic
purpose. 2) Mid infrared - The mid- infrared which is approximately 4000- 400
cm-1
(3.0 – 2.5 μm) may be used to study the fundamental vibrations and
associated rotational vibrational structure. Spectroscopy in this region is
extremely useful for the study of organic compounds. 3) Far infrared - The far
infrared region 400-10 cm-1
(1000-30 μm) is also not of much use for organic
spectroscopy. Since only few useful absorptions occur in the far infrared region
(400-10 cm-1
), (1000-30 μm)
171
• As bond order increases, force constant increases and frequency increases while
bond length decreases.
• The bond between heavier atoms vibrate at low frequency and stronger bond
between atoms vibrate at high frequency.
• The change in bond length or angle due to vibrational or rotational motion
causes a net change in dipole moment of the molecule.
5.2 FACTORS AFFECTING IR ABSORPTION :
The following factor which affect on IR absorption
5.2.1 HYDROGEN BONDING :
Hydrogen bonding has held particular interest in recent years due to the
central role it plays with regard to molecular recognition in both biological and
artificial systems [7-10].
When a carbonyl group is involved in hydrogen bonding its C=O stretching
frequency is lowered. The strength of hydrogen bond is at a maximum when the
proton donor group and the axis of the lone pair orbital are collinear. The strength
of the bond decreases as the distance between proton donor group and proton
acceptor group increases.
Intramolecular H- bonding shows greater effect on C=O and O–H
stretching frequencies than intermolecular H- bonding. The effect of
concentration on intramolecular and intermolecular H- bonding is markedly
different. The bands that result from intermolecular bonding generally disappear
at low concentrations. Intramolecular H- bonding persists at very low
concentrations.
IR spectroscopy is the leading method for identification of hydrogen
bonds. For instance the formation of an O-H--O hydrogen bond elongates and
weakens the O-H bond. The resulting red shift of the O-H bond stretching
frequency can be easily detected in the IR spectra and its magnitude indicates the
strength of the hydrogen bond [11].
172
The hydrogen bonding changes the C-H bond length very little and in
some cases even shortens it, leading to the blue shift of C-H bond strength
frequency. This phenomenon is called anti-hydrogen bond [12,13]. However,
Scheiner et al. [14] have concluded, from a set of careful calculations that
“antihydrogen” bonds do not differ fundamentally from conventional hydrogen
bonds. According to their results, the electron density redistribution upon
hydrogen bond formation is similar for both the C-H--O and O-H--O interactions.
The hetero aromatic compounds and their derivatives are structurally very
close to benzene. In aromatic compound, C-H stretching vibrations occur in the
region 3000-3100 cm-1
and for saturated alkane near 2950-3000 cm-1
. In
heterocyclic compounds, C-H stretching vibration bands are usually weak.
Absorption arising from C-H stretching in the alkane occurs in the general region
of 2850-3000 cm-1
.
The non hydrogen-bonded hydroxyl group of phenols absorb strongly in
the 3584-3700 cm-1
region. The sharp free hydroxyl bands are observed in the
vapour phase and in very dilute solution in non polar solvent [15].
Acidity and basicity, molecular geometry and Ring strain of the proton
donor and acceptor groups affect the strength of bonding. Hydrogen bonding is
strongest when the bonded structure is stabilized by resonance.
The hetero aromatic compounds and their derivatives are structurally very
close to benzene. In aromatic compound, C-H stretching vibrations [16] occur in
the region 3000-3100 cm-1
and for saturated alkane near 2950-3000 cm-1
. In
heterocyclic compounds, C-H stretching vibration bands are usually weak [17].
Absorption arising from C-H stretching in the alkane occurs in the general region
of 2850-3000 cm-1
.
5.2.2 INDUCTIVE EFFECTS :
Groups which have electron withdrawing inductive effects (-I ) when
attached to functional groups increase the stretching frequency. On the other
hand, group which have electron donating inductive effects (+I) when attached to
functional groups decrease the stretching frequency.
173
5.2.3 RESONANCE EFFECT :
The group which have electron withdrawing resonance effects, (-R)
when attached to functional groups, increase the stretching frequency and groups
which have electron donating resonance effects (+R) decrease the stretching
frequency.
5.2.4 STERIC EFFECT :
Steric effects also modify the stretching frequencies. When the number of
conjugated double bond increases, the effect is further increase and the further
lowering of stretching frequency takes place.
5.3 INTERPRETATION OF IR :
IR spectroscopy provides a fast and effective way to identify functional
groups present in a molecule by looking to absorptions corresponding to the bond
types present in these functional groups.
Functional group organic compounds has absorption which is characteristic
not only in position but also in largely dependent on an appreciation of the
intensities of the observed bands. Analysis of the spectrum of an unknown
compound requires the determination of the presence or absence of a few major
functional groups. The and NO2 peaks are
most conspicuous and give immediate structural information if they are present.
When assigning peaks to specific groups in the infrared region it is
usually the stretching vibrations which are most useful
174
TABLE OF SOME CHARACTERISTIC IR ABSORPTION
Frequency, cm–1
Bond Functional group
3100–3000 (s) C–H stretch aromatics
1750–1735 (s) C=O stretch esters, saturated aliphatic
1600–1585 (m) C ⃛C stretch (in–ring) aromatics
1500-1400 C ⃛C stretch (in–ring) aromatics
1320–1000 (s) C–O stretch alcohols, carboxylic acids,
900–675 (s) C–H "Bending" aromatics
3600-3650 OH Free Alcohol and Phenols
3200-3500 OH Bonded H Bonded alcohols and
phenols
3450-3600 OH Sharp Intramolecular H bond
3200-3550 OH Broad Intramolecular H bond
740-860 Ar –Cl stretch aryl halides
1050 C-O Primary alcohol
1000 C-O Secondary alcohol
1150 C-O Tertiary alcohol
1230 C-O Aromatic alcohol
175
IR Frequencies ) for pure compounds
Compound
-
strech
Aromatic
C-H
strech
Methyl
C-H
strech
Ar-Cl
strech
Ar-
strech
N-H
strech
t-Butanol 3377.47 - - - - -
Benzene - 3036.06 - - - -
Chlorobenzene - 3066.92 - 740.69 - -
Toluene - 3072.38 - - - -
o-Chlorotoluene - 3068.85 - 746.48 - -
p-Chlorotoluene - 30.3027 - 806.27 - -
o-Xylene - 3016.77
2970.48
2939.61
2920.32
- - -
m-Xylene - 3016.77 2920.29
2864.39 - - -
p-Xylene - 3022.55 2966.62
2933.83 - - -
Nitrobenzene - 3076.58 - -
1348.29
Sym
1518.03
Asym
-
Aniline - 3033.56 - - -
3356.25
Sym
3433.25
Asym
Sym = Symmetrical
Asym = Asymmetrical
176
5.4 LITERATURE SURVEY :
The presence of intramolecular hydrogen bond in o-nitroaniline was
investigated by studying the IR spectrum [18] of the compound in different proton
accepting solvents. Frequency shift of the symmetric and symmetric N-H
stretching bands showed formation of associated species with the solvents.
Analysis of shift pattern showed the presence of hydrogen bond in o-nitroaniline.
Chemical shift data for hydroxyl protons were studied [19] to calculate a
structure factor, related to an apparent number of hydrogen bonds broken, when 1,
4-dioxane was added to methanol, ethanol, 2-propanol and 2-methyl -2-propanol.
The result depends on the different content of partially unbounded OH groups in
liquid water and alcohols.
Excess dielectric polarizations, IR and NMR studies [20] of the mixtures
of ethyl iodide with benzene, toluene, o-xylene and p-xylene were carried out. IR
and NMR spectral studies supported the conclusions drawn from dielectric
polarization measurements.
The use of IR, UV-visible absorption spectroscopy was illustrated [21] to
determine thermodynamic properties and other specific chemical interactions in
alcohols.
The OH proton chemical shifts of methanol referred to the CH3 proton in
the methanol- benzene-d6 systems were measured [22] at room temperature up to
the supercritical region. MD simulations were performed at the same composition
as experiment at 575 K. The chemical shift results in the supercritical region were
in good agreement with those of pure methanol at the density within experimental
errors. The results of NMR and MD simulation suggest that the hydrogen bonded
structure of methanol was practically not affected by addition of benzene
molecule.
The thermodynamic properties of H-bonding solutions, Fourier-trans
formed infrared (FT-IR) spectroscopic investigations of 14 binary systems of the
type (alcohol or phenol) + hydrocarbon were carried out [23] at temperatures of
283, 298 and 313 K. FT-IR spectroscopy provides quantitative information on the
distribution of the alcohol molecules into the monomer and H-bonded species,
respectively. Furthermore, direct evidence on the type of H-bonded species is
177
obtained. In addition to the FT-IR data, NMR data were taken for the system
1-butanol + cychlohexane, primarily to test the infrared (IR) spectroscopic results.
The results provided a large data base for the development of thermodynamic
models of H-bonding solutions.
Brown [24] determined the IR spectrum of benzene in matrices of Kr and
Ar and showed to be strongly affected by aggregation of the benzene. The
vibrational frequencies for benzene isolated in the Ar matrix were in good
agreement with those measured in the gas phase, but the measured absolute
intensities disagreed drastically with gas phase measurements (by at least 100%).
For benzene in Kr matrices accurate absolute intensities were obtained that were
in good agreement with gas phase studies when corrected for the effective field
factor.
Adsorption of benzene and ethylbenzene on the acidic and basic sites of
beta zeolite were studied by [25]. The adsorption of benzene on Na beta and Cs
beta followed by IR spectroscopy showed two pairs of CH out-of-plane bands.
They were assigned to benzene interacting with either the cations, acidic sites or
cations. In addition species similar to liquid benzene were detected below
saturation of the adsorption sites.
Scotoni et al. [26] investigated infrared spectroscopy of CH strectching
models of partially F-substituted benzenes, and the fundamental spectrum of
fluorobenzene. They reported the study of the fundamental transitions of
fluorobenzene in the wave numbers range from about 3000 to 3150 cm-1
. They
showed, how benzene algebraic procedures must be modified for taking into
account the effects induced by the substitution of one hydrogen atom with
fluorine, i.e., (i) the reduction of symmetry and (ii) the frequency (chemical) shift
due to the change of electron distribution.
The interactions of n-heptane, benzene, and toluene with HZSM5 and
MO-HZSM catalysts were studied by [27] FTIR spectroscopy. The FTIR study
indicates that there were interactions of heptanes, benzene, and toluene with both
the strongly acidic internal OH’s and the less acidic silanol groups in HZSM5.
Thermodynamic properties of the binary systems of toluene with butyl
methacrylate, allyl methacrylate, methacrylic acid and vinyl acetate at 20, 30 and
178
40 C were reported by Wisniak et al. [28]. The C = O group of butyl
methacrylate presents and IR absorption at 1717.36 wave numbers that increases
to 1718.24 components that result in the displacement of the absorption band.
Nevertheless, the system toluene + butyl methacrylate presents negative excess
volumes, suggesting that the molecular orbital of toluene do interact with those of
the acrylic group. The C = O group of pure vinyl acetate presents an IR absorption
band at 1758.31 cm-1
, which in an equimolar mixture with toluene moves to group
of vinyl acetate is prevented from conjugation with the double bond by the
presence of an oxygen atom.
Grinvald et al. [29] reported IR Fourier spectroscopy proofs of the
existence of supramolecular structures formed by and σ hydrogen bonds in the
liquid phase of aromatic systems such as benzene and its monosubstituted
derivatives C6H5X ( X= CH3, Br, NO2) and their deuterated analogues C6D5X (X=
CD3, Br, NO2).
5.5 RESULTS AND DISCUSSION :
IR measurement for mixtures of t-butanol with aromatic hydrocarbon over
the entrie composition range has been carried out. The change in the frequencies
values –OH group in not much for the mixtures of t-butanol with toluene, p-
chlorotoluene, o-chlorotoluene and chlorobenzene. Where as for the other binary
mixtures, the –OH frequencies show some changes. In order to have an insight
into the nature of interaction between the components of liquid mixtures, the
change in IR frequencies of –OH group is calculated as,
IR frequencies of –OH group in the mixture – IR frequencies of –OH group
in the pure t-butanol.
It is seen that the values are negative for benzene, xylenes and aniline
while positive for nitrobenzene. It is concluded that there is variable degree of
intermolecular hydrogen bonding between the components of the mixtures.
It is interesting to note here that toluene and chloro substituted benzenes
do not show any changes in the frequencies of –OH group. It is also seen that the
Ar-Cl frequencies do not show any changes in chlorobenzene, o-chlorotoluene
and p-chlorotoluene.
179
In case of mixtures of t-butanol with toluene and xylenes sp3 (C-H)
frequencies show no changes with respective to the composition range. It is also
seen that these frequencies show almost an independent character with respect to
the position of the additional –CH3 group in xylenes ).
In case of mixture of t-butanol with nitrobenzene the symmetrical
(Ar-NO2) changes from 1348 in pure nitrobenzene to 1365 for 0.2
mole fraction of t-butanol but there after it shows no changes from the pure values
for t-butanol + Aniline, (N-H) symmetrical frequencies decreases from
3356 for pure aniline and the changes is maximum for 0.4 to 06. mole
fraction of t-butanol
180
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Franciso, 1990.
2) Joseten M D, Schaad L, Hydrogen Bonding; Marcel Dekker, New York,
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3) Vinogradav S N, Linnel R H, Hydrogen Bonding; Van Nostrand Reinhold,
New Yark,1971.
4) Legon A C, Millen D, J Chem Soc. Rev, 21 (1992) 71.
5) Scheiner S, Acc. Chem Res, 27 (1994) 402.
6) Etter M C, Acc. Chem Res, 23 (1990) 120.
7) Desirajau G R, Crystal Engineering: “The Design of Organic Solids”,
Elsevier Amsterdam (1989).
8) Jeffery G A, Saenger W, “Hydrogen Bonding in Biological Structures”,
Springer- Verlag Barlin, (1991).
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10) Kirby A J, Acc. Chem Res, 30 (1997) 290.
11) Wang B, Hinton J F, Polay P, J Phys Chem, 107 (2003) 4683.
12) Cubero E, Orozco M, Hobza P, Luque F, J Phys Chem, 103 (1999) 6394.
13) Hobza P, Havlas Z, Chem Phys Lett, 303 (1999) 447.
14) Scheiner S, Kr T, J Phys Chem, 106 (2002) 1784.
15) Silverstein R M, Webster F X “Spectrometric Identification of Organic
Compounds”, 6th
Ed, New York (2006).
16) Gunasekaran S, Natarajan R K, Rathika R, Syamala D, Indian J Pure
Appl Phys, 43 (2005) 509.
17) Gunasekaran S, Kumaresan S, Seshadri S, Muthu S, Indian J PureAppl
Phys, 46 (2008) 155.
18) Parimala S G, Indian J Chem 27A (1988) 947.
19) Mirti P, J Mol Liq, 38(1988) 215.
20) Singh K C, Kalra L C, Prashkumar, Indian J Chem, 29A(1990) 779.
21) Johnston K P, Meredith J, C Harrison K L, Fluid Phase Equilib,
116 (1996) 385.
22) Asahi N, Nakajmura Y, J Mol Liq, 90 (2001) 85.
23) Asprion N, Hasse H, Maurer G, Fluid Phase Equilib, 186 (2001) 1.
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24) Brown K, Spectrochimica Acta Part A Mol Spectroscopy, 34 (1978) 117.
25) Dzwigaj S, Mallmann A, Barthomeuf D, J Chem Soc. Faraday Trans,
86 (1990) 431.
26) Scotoni M, Oss S, Lubich L, Furlani S, Bassi D, J Chem Phys,
103 (1995) 897.
27) Alejandre A G, Gonzalez H, Ramirez J, Ind Eng Chem Res,
40 (2001) 3484.
28) Wisniak J, Cortez G, Peralta R D, Infante R, Elizalde L E, J Solution Chem,
36 (2007) 997.
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182
Table 5.1 : IR Frequencies ) for t-Butanol with Benzene
Mole fraction of t-Butanol
(O-H)
Benzene -
0.2 3360.11
0.4 3362.04
0.5 3354.32
0.6 3365.90
0.8 3348.54
t-Butanol 3377.47
183
Table 5.2 : IR Frequencies ) for t-Butanol with Chlorobenzene
Mole fraction of
t-Butanol
(O-H) (Ar-Cl)
Chlorobenzene - 740.69
0.2 3375.54 744.65
0.4 3381.33 742.62
0.5 3375.54 740.69
0.6 3383.26 740.69
0.8 3381.33 740.69
t-Butanol 3377.47 -
184
Table 5.3 : IR Frequencies ) for t-Butanol with Toluene
Mole fraction of t-Butanol
(O-H)
Toluene -
0.2 3379.51
0.4 3377.47
0.5 3379.40
0.6 3377.47
0.8 3383.26
t-Butanol 3377.47
185
Table 5.4 : IR Frequencies ) for t-Butanol with o-Chlorotoluene
Mole fraction of
t-Butanol
(O-H) (Ar-Cl)
o-Chlorotoluene - 746.81
0.2 3373.61 748.41
0.4 3377.47 748.41
0.5 3373.61 748.41
0.6 3373.47 748.41
0.8 3371.68 746.48
t-Butanol 3377.47 -
186
Table 5.5 : IR Frequencies ) for t-Butanol with p-Chlorotoluene
Mole fraction of
t-Butanol
(O-H) (Ar-Cl)
p-Chlorotoluene - 806.27
0.2 3379.40 806.27
0.4 3379.40 806.27
0.5 3379.40 806.27
0.6 3389.33 806.27
0.8 3367.82 806.27
t-Butanol 3377.47 -
187
Table 5.6 : IR Frequencies ) for t-Butanol with o-Xylene
Mole fraction of
t-Butanol
(O-H) (C-H) methyl
o-Xylene -
2970.48
2939.61
2920.32
0.2 3362.04
2970.48
2939.61
2920.32
0.4 3367.82
2972.40
2941.54
2875.96
0.5 3362.04
2972.40
2941.54
2875.96
0.6 3348.54
2972.40
2939.61
2875.96
0.8 3329.25
2970.48
2939.61
2920.32
t-Butanol 3377.47 -
188
Table 5.7 : IR Frequencies ) for t-Butanol with m-Xylene
Mole fraction of
t-Butanol
(O-H) (C-H) methyl
m-Xylene -
2920.32
2868.39
2731.29
0.2 3379.75
2972.40
2941.54
2874.03
0.4 3358.18
2972.40
2926.11
2872.10
0.5 3350.48
2972.40
2924.18
2872.10
0.6 3346.61
2972.40
2922.25
2870.17
0.8 3342.88
2970.48
2922.25
2866.32
t-Butanol 3377.47 -
189
Table 5.8 : IR Frequencies ) for t-Butanol with p-Xylene
Mole fraction of
t-Butanol
(O-H) (C-H) methyl
p-Xylene -
2933.83
2874.03
2966.62
0.2 3373.61
2972.40
2939.61
2875.96
0.4 3373.61
2972.40
2967.68
7875.96
0.5 3367.82
2972.40
2967.68
7875.96
0.6 3369.75
2972.40
2967.68
7875.96
0.8 3331.18
2968.55
2933.83
2874.03
t-Butanol 3377.47 -
190
Table 5.9 : IR Frequencies ) for t-Butanol with Nitrobenzene
Mole fraction of
t-Butanol
(O-H) (Ar- )
Nitrobenzene - Symm - 1348.29
Asymm - 1518.03
0.2 3377.47 Symm - 1365.65
Asymm - 1529.60
0.4 3381.33 Symm - 1348.29
Asymm - 1527.67
0.5 3396.76 Symm - 1348.29
Asymm - 1527.67
0.6 3417.98 Symm - 1348.29
Asymm - 1525.75
0.8 3574.21 Symm - 1348.29
Asymm - 1523.82
t-Butanol 3377.47 -
191
Table 5.10 : IR Frequencies ) for t-Butanol With Aniline
Mole fraction of
t-Butanol
(O-H) (N-H)
Aniline - Symm - 3356.25
Asymm - 3433.41
0.2 3375.54 Symm - 3337.99
Asymm - 3078.49
0.4 3360.11 Symm - 3037.99
Asymm - 3074.63
0.5 3358.18 Symm - 3037.99
Asymm - 3074.63
0.6 3356.25 Symm - 3037.99
Asymm - 3372.71
0.8 3356.25 Symm - 3336.06
Asymm - 3372.71
t-Butanol 3377.47 -
192
Figure 4.1 Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum)
of t-Butanol
193
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.2 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + Benzene.
194
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.3 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + Chlorobenzene.
195
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.4 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + Toluene.
196
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.5 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + o-Chlorotoluene.
197
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.6 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + p-Chlorotoluene.
198
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.7 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + o-Xylene.
199
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.8 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + m-Xylene.
200
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.9 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + p-Xylene.
201
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.10 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + Nitrobenzene.
202
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.11 : Neat FTIR -OH Frequency (cm-1
) Cut Section (Spectrum) of
t-Butanol + Aniline.
203
Figure 4.12 : Neat FTIR Ar-Cl Frequency (cm-1
) Cut Section (Spectrum) of
Chlorobenzene.
204
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.12 : Contd- Neat FTIR Ar-Cl Frequency ( cm-1
) Cut Section
(Spectrum) of t-Butanol + Chlorobenzene.
205
Figure 4.13 : Neat FTIR Ar-Cl Frequency (cm-1
) Cut Section (Spectrum) of
o-Chlorotoluene.
206
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.13 : Contd- Neat FTIR Ar-Cl Frequency ( cm-1
) Cut Section
(Spectrum) of t-Butanol + o-Chlorotoluene.
207
Figure 4.14 : Neat FTIR Ar-Cl Frequency (cm-1
) Cut Section (Spectrum) of
p-Chlorotoluene.
208
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.14 : Contd- Neat FTIR Ar-Cl Frequency ( cm-1
) Cut Section
(Spectrum) of t-Butanol + p-Chlorotoluene.
209
Figure 4.15 : Neat FTIR Sp3 C-H Frequency (cm
-1) Cut Section (Spectrum)
of o-Xylene.
210
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.15 : Contd- Neat FTIR SP3 C-H Frequency (cm
-1) Cut Section
(Spectrum) of t-Butanol + o-Xylene
211
Figure 4.16 : Neat FTIR Sp3 C-H Frequency (cm
-1) Cut Section (Spectrum)
of m-Xylene
212
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.16 : Contd- Neat FTIR Sp3 C-H Frequency (cm
-1) Cut Section
(Spectrum) of t-Butanol + m-Xylene
213
Figure 4.17 : Neat FTIR Sp3 C-H Frequency (cm
-1) Cut Section (Spectrum)
of p-Xylene
214
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.17 : Contd- Neat FTIR Sp3 C-H Frequency (cm
-1) Cut Section
(Spectrum) of t-Butanol + p-Xylene
215
Figure 4.18 : Neat FTIR Ar-NO2 Frequency (cm-1
) Cut Section (Spectrum)
of Nitrobenzene
216
x1 = 0.2 x1 = 0.4 x1 = 0.5
Figure 4.18 : Contd- Neat FTIR Ar-NO2 Frequency ( cm-1
) Cut Section
(Spectrum) of t-Butanol + Nitrobenzene.
217
Figure 4.19 : Neat FTIR N-H Frequency (cm-1
) Cut Section (Spectrum)
of Aniline
218
x1 = 0.4 x1 = 0.5 x1 = 0.6
Figure 4.19 : Contd- Neat FTIR N-H Frequency (cm-1
) Cut Section (Spectrum)
of t-Butanol + Aniline