Journal of Molecular Structure 655 (2003) 89–95

www.elsevier.com/locate/molstruc

Experimental and theoretical IR and Raman spectra of picolinic,

nicotinic and isonicotinic acids
P. Koczońa,b,*, J.Cz. Dobrowolskic,d, W. Lewandowskib,d, A.P. Mazurekd
a
Department of Chemistry, Warsaw Agricultural University, Nowoursynowska 159 C, Warsaw 02-728, Poland
b
Department of Chemistry, Białystok Technical University, Zamenhofa 29, Białystok 15-435, Poland
c
Industrial Chemistry Research Institute, Rydygiera 8, Warsaw 01-793, Poland
d
Drug Institute, Chełmska 30/34, Warsaw 00-725, Poland
Received 3 October 2002; revised 6 March 2003; accepted 31 March 2003

Abstract
The experimental and theoretical (B3PW91/6-311þ þG**) vibrational (IR and Raman) spectra of picolinic, nicotinic and
isonicotinic acids (pyridine-2-, -3-, and -4-carboxylic acid, respectively) were studied. Three stable calculated structures were
found for picolinic acid: the structure with intramolecular hydrogen COOH· · ·N bond, and the two without hydrogen bond. For
the nicotinic acid two stable theoretical structures differ in orientation of the COOH group with respect to the nitrogen atom,
whereas for the isonicotinic acid only one form was stable. The theoretical vibrational spectra of the three acids were interpreted
by means of potential energy distributions (PEDs) using VEDA 3 program. Next, selected experimental bands were assigned
based on the scaled theoretical wavenumbers. Finally, the wavenumbers and intensities for the three isomeric acids were
compared and discussed in terms of location of the carboxylic group.
q 2003 Elsevier Science B.V. All rights reserved.
Keywords: Raman spectra; Wavenumbers; Potential energy distributions; Nicotinic acid; Isonicotinic acid; Picolinic acid

1. Introduction different methods. The biological importance of

The benzene derivatives are compounds of great
interest in term of chemical and biological properties.
Benzoic acid and its derivatives are commonly used
food preservatives, as well as antiseptic agents applied
in various industrial branches (foods, pharmaceutics,
textile, cosmetics) [1,2]. The picolinic [3], nicotinic
[4] and isonicotinic acids [5] and its complexes with
different metals were thoroughly investigated by
* Corresponding author.
E-mail address: koczon@delta.sggw.waw.pl (P. Koczoń).
0022-2860/03/$ - see front matter q 2003 Elsevier Science B.V. All rights reserved.
doi:10.1016/S0022-2860(03)00247-3
three isomeric compounds and especially its com-
plexes are described in the literature [6 –10].
In our previous papers we characterise aromaticity
by comparison of vibrational spectra of studied
benzene derivatives with those of benzene [11 –13].
As a molecular standard of aromatic system we take
selected normal vibrations of benzene ring, mainly in
the following ranges: 1650 – 1350 cm21 [n(C – C)
vibrations], , 1300 – 1000 cm21 [b(CH) deforma-
tion in plane], , 1000 – 700 cm21 [g(CH) defor-
mation out-of-plane], , 700 – 550 cm21 [f(CC)
deformation out-of-plane]. The number, wavenumbers
90 P. Koczoń et al. / Journal of Molecular Structure 655 (2003) 89–95
and intensities of the IR and Raman active bands due to
skeletal vibrations of the ring were analysed, as well as
wavenumbers of the electronic bands due to transitions
between the bonding and antibonding orbitals of the
aromatic system. Our intention has been to find a
correlation between changes of the molecular reactiv-
ity and the electronic and topological structure of the
considered molecules. Hence, one of the first steps is to
learn basic features of molecular vibrations, which is
not possible without detailed knowledge of vibrational
spectra.
In this paper picolinic, nicotinic and isonicotinic
acids were under study. Experimental spectra were
interpreted in terms of calculated ones at
B3PW91/6-311þ þ G** level. The aim of this paper
was to assign the selected bands (the regions: 3450–
3050 cm21, 1717 – 1597 cm21 and 1455 – 1370 cm21)
and estimate the influence of nitrogen atom position
with respect to the carboxylate group on the
vibrational structure of the molecule. An attempt is
made to find a correlation between nitrogen position
and aromaticity of the molecule. Here, we interpreted
the calculated spectra in terms of potential energy
distributions (PEDs) and made the assignment of
selected experimental bands due to PED analysis
results.
2. Experimental
Pressed KBr pellets were used for IR measure-
ments within the range of 4000– 400 cm21 with a
Perkin Elmer System 2000 FT-IR spectrometer. The
spectrum of water solution of picolinic acid in the
region 3500 –1300 cm21 was recorded with ATR
accessory of Perkin Elmer System 2000. Raman
spectra of solid-state samples in capillary tubes were
recorded within the range of 4000– 400 cm21 with a
FT-NIR Raman accessory of a Perkin Elmer System
2000. The ab initio calculations were carried out with
the Gaussian 98 system of programs [14]. Full
optimisation of studied molecules was performed at
B3PW91 level combined with the 6-311þ þ G**
basis set. Calculations were executed on SGI
computers.
The theoretical vibrational spectra of the three
acids were interpreted by means of PEDs using
VEDA 3 program [15].
3. Results and discussion
3.1. Energetics
The calculated total energies of picolinic, nicotinic,
and isonicotinic acids monomers are listed (Table 1).
The picolinic acid monomer can exist in three
conformations, the nicotinic monomer in two confor-
mations, whereas that of isonicotinic in only one form.
From the relative energies gathered in Table 1 and
from Fig. 1 it is evident that the structure of picolinic
acid with intramolecular hydrogen COOH· · ·N bond
is the most stable one. The other two are less stable by
3.50 and 3.67 kcal/mol, respectively. The nicotinic
and isonicotinic acids are isomers of picolinic acids
and are less stable than the most stable picolinic acid
molecule by 1.88 and 2.48 kcal/mol, respectively.
3.2. Vibrational spectra
The calculated structures of all three isomeric
molecules are planar. As build of 14 atoms, they
exhibit 36 fundamental vibrations. Hydrogen bonding
in the condensed phase with the other acid molecules
makes vibrational spectra more complicated. The
vibrational spectra can be divided into four spectral
regions where different kinds of normal modes exhibit
their activity. In the spectral range over 3000 cm21,
O –H and C – H stretches occur. The C –C and COOH
group stretching vibrations occur in the range of
1800– 1500 cm21. In the 1500 –1350 cm21 range two
of mixed modes involving contributions from n(C –C)
stretches as well as n(O – H) in plane deformations are
observed. Below 1350 cm21 down to 400 cm21
Table 1
The B3PW91/6-311þþ G** calculated total energies (hartree) for
conformers of picolinic, nicotinic and isonicotinic acid molecules
and relative energy referred to the most stable conformer of
picolinic acid (kcal/mol)
Structure Energy Energy difference
Picolinic acid (structure 1) 436.812870 0.000
Picolinic acid (structure 2) 436.807020 3.67
Picolinic acid (structure 3) 436.807292 3.50
Nicotinic acid (structure 1) 436.809877 1.88
Nicotinic acid (structure 2) 436.808914 2.48
Isonicotinic acid 436.713873 3.15
 P. Koczoń et al. / Journal of Molecular Structure 655 (2003) 89–95 91

Fig. 1. The atoms numbering in the structures of picolinic, nicotinic and isonicotinic acids.

several characteristic in plane deformations b(C– H),

Table 2
out-of-plane g(C– H) and f(CCC) vibrations as well as
The definitions of in plane local modes calculated for picolinic acid
conformers and notation used in this paper out-of-plane (CCC) deformations take place. The aim
of the present paper is to compare some of the selected
Mode form Notation

n(O9 –H) n(OH) Table 3

n(C3 –H) þ n(C4 –H) þ n(C5 –H) þ n(C6 –H) n S(CH)P The definitions of local in plane modes calculated for nicotinic acid
n(C6 –H) þ n(C5 –H) þ n(C4 –H) 2 n(C3 –H) na1(CH)P conformers and notation used in this paper
n(C6 –H) þ n(C3 –H) 2 n(C4 –H) þ n(C5 –H) na2(CH)P
n(C6 –H) 2 n(C5 –H) þ n(C4 –H) 2 n(C3 –H) na3(CH)P Mode form Notation
n(C7yO) n(CyO)
n(N –C6) 2 n(C5 – 6) þ n(C3 –C4) þ n(C2 –C3) n1(CyC)P n(O9 –H) n(OH)
n(N –C6) 2 n(C4 –C5) þ n(C3 –C4) þ n(N –C2) n(C4 – H) þ n(C5 – H) n S(CH)N
conformer 1 n(C2 – H) 2 n(C4 –H) þ n(C5 –H) þ n(C6 –H) na1(CH)N
n(N –C2) 2 n(C5 –C6) þ n(C4 –C5) þ n(C3 –C4) n2(CyC)P n(C2 – H) 2 n(C5 –H) na2(CH)n
2 n(C2 –C3) conformer 2 n(C6 – H) 2 n(C5 –H) n a3(CH)N
n(N –C6) þ n(C5 –C6) þ n(C4 – C5) þ n(C3 –C4) n(C7yO) n(CyO)
þ n(C2 – C3) 2 n(N –C2) conformer 3 n(N–C2) 2 n(C2 –C3) 2 n(C3 – C4) þ n(C4 –C5) n1(CyC)N
n(N –C2) 2 n(C5 –C6) 2 n(C3 –C4) þ n(C2 –C3) n3(CyC)P 2 n(C5 –C6) 2 n(NC6) þ n(C3 –C7)
n(N –C6) 2 n(N –C2) 2 n(C3 –C4) 2 n(C3 –C2) n(N–C2) 2 n(C2 –C3) þ n(C3 –C4) 2 n(C5 –C6) n2(CyC)N
conformer 1 þ n(N –C6)
n(N –C6) 2 n(C3 –C4) 2 n(C3 –C2) conformer 2 n4(CyC)P n(C3 – C7) 2 n(C3 –C4) 2 n(C4 –C5) þ n(N –C6) n3(CyC)N
n(N –C6) 2 n(N –C2) 2 n(C3 –C4) 2 n(C3 –C2) þ n(N –C2)
conformer 3 n(N–C2) þ n(C2 – C3) 2 n(C3 –C4) 2 n(C5 –C6) n4(CyC)N
b(O9 – H) b(O–H) b(O9 –H) b(O–H)
92 P. Koczoń et al. / Journal of Molecular Structure 655 (2003) 89–95

Table 4 vibrational bands of all three isomeric molecules rather

The definitions of local modes calculated for isonicotinic acid and than go deeply into a vibrational behaviour of the acids
notation used in this paper
in their condensed phases. Therefore, we focus our
Mode form Notation attention on the following vibrations: CH stretching
vibrations, OH stretching and in plane deformation
n(O9 –H) n(OH) vibrations, CyO stretching vibrations and some CC
n(C3 –H) þ n(C2 –H) nS1 (CH)I
n(C5 –H) þ n(C6 –H) nS2 (CH)I stretching vibrations. The spectrum of water solution
n(C2 –H) 2 n(C5 –H) na2(CH)I of picolinic acid was registered and wavenumbers of
n(C2 –H) 2 n(C3 –H) þ n(C5 –H) 2 n(C6 –H) na3(CH)I analysed bands are within the experimental error
n(C7yO) n(CyO)
n(N –C2) 2 n(C2 –C3) þ n(C3 –C4) þ n(C4 –C7) n1(CyC)I (4 cm21) the same as in case of solid-state samples.
þ n(C4 – C5) 2 n(C5 –C6) þ n(N–C6) This work is a part of our research program in which we
n(N –C2) 2 n(C3 –C4) þ n(C4 –C5) 2 n(N –C6) n2(CyC)I are looking for correlation between molecular struc-
n(N –C2) 2 n(C3 –C4) 2 n(C4 –C5) þ n(C4 –C7) n3(CyC)I
þ n(N–C6)
ture and macroscopic properties of the chemical
n(C2 –C3) 2 n(C5 –C6) n4(CyC)I compounds and investigate the influence of metal
b(O9 –H) b(O–H) ions on the electronic charge distribution of complexes

Table 5
The 3500–3000 cm21 region in the IR and Raman experimental and scaled calculated spectra of picolinic, nicotinic and isonicotinic acids

Molecule Experimental B3PW91/6-311þ þ G**

IR (cm21) Raman (cm21) ncalc (cm21) IR Intensity (km/mol) Raman Activity Assignment, PED%
(A4/Amn)

Picolinic acid 1 3437 m – 3443 187.3 45.6 99 n(O –H)

3112 w 3113 s 3103 1.94 120.1 93 na3(C–H)P
3090 vw 3092 s 3074 6.6 163.1 79 na1(C–H)P
3055 vw 3055 w 3073 5.9 79.9 78 n S(C –H)P
– 3029 w 3057 9.3 93.1 91 na2(C–H)P
Picolinic acid 2 3653 100.4 134.5 100 n(O –H)
3107 0.7 101.7 94 n S(C –H)P
3085 10.5 179.7 93 na1(C–H)P
3068 6.3 80.5 92 na2(C–H)P
3043 13.6 105.2 94 na3(C–H)P
Picolinic acid 3 3650 95.7 134.8 100 n(O –H)
3101 2.3 110.9 90 na2(C–H)P
3086 9.2 162.9 85 na3(C–H)P
3070 6.2 80.2 87 n S(C –H)P
3045 14.3 105.9 94 na1(C–H)P
Nicotinic acid 1 3447 m 3651 107.9 133.4 100 n(O –H)
3104 w 3093 5.6 148.9 94 na2(C–H)N
3084 w 3079 3.3 91.2 87 na3(C–H)N
3071 m 3073 3.5 52.8 90 na1(C–H)N
3042 w 3046 13.3 113.6 89 n S(C –H)N
Nicotinic acid 2 3651 104.7 138.3 100 n(O –H)
3099 2.7 113.6 86 na3(C–H)N
3080 7.0 127.7 83 na1(C–H)N
3068 1.2 52.3 98 n S(C –H)N
3046 12.9 112 94 na2(C–H)N
Isonicotinic acid 3436 m – 3651 103.6 135.2 100 n(OH)
3104 w 3107 w 3121 1.6 102.6 97 nS1 (C– H)I
3084 w 3086 s 3115 2 85.8 97 na2(C–H)I
3072 w 3073 m 3073 5.6 130.5 91 na1(C–H)I
3054 w 3056 w 3070 26 107.5 92 nS2 (C– H)I
 P. Koczoń et al. / Journal of Molecular Structure 655 (2003) 89–95 93

of various benzoic acid derivatives [16,17]. So, to get
information about electronic charge distribution in the
molecule of the ligands, we have to assign their
vibrational spectra. The proper assignment let us to
estimate the strength and length of the bonds and intra
and inter molecular interaction. In case of salicylates
the influence of metal on the electronic structure of
salicylic acid is much higher than in case of benzoates.
This is the result of presence of quasiaromatic
hydrogen bonds in salicylic acid molecules of the
most stable structure and breaking of these bonds
during process of complexation [18]. In case of the
picolinic acid, the hydrogen bond is also present
(Table 1, Fig. 1). The influence of the metals on the
picolinic acid most stable structure will be investigated
in a separate paper.
In Tables 2– 4 the local mode forms and their
notations used here are gathered for picolinic,
nicotinic, and isonicotinic acids. The experimental
IR and Raman wavenumbers, calculated (scaled) IR
wavenumbers and intensities as well as assignment
and PEDs in the range of 3500 – 1800 cm21 for the all
studied structures are gathered in Table 5. Theoretical
wavenumbers were calculated according to the
formulae: nscaled ¼ 0:955 £ ncalculated þ 25:7 [19]. In
Table 6 the experimental IR and Raman wavenum-
bers, the calculated (scaled) IR wavenumbers and
intensities, as well as the assignment and PEDs in the
range of 1800 – 1500 cm21 for all the structures
studied are gathered. In Table 7 the experimental IR
and Raman wavenumbers, the calculated (scaled) IR
wavenumbers and intensities as well as the assign-
ment and PEDs in the range of 1500 –1350 cm21 for
the all studied structures are gathered.
The atoms of the acids show very similar
movement that is responsible for bands occurring
in three analysed regions. The presence of nitrogen
in aromatic ring and its position versus carboxylic
anion influence the mode form very slightly
(Tables 2 – 4), but in the experimental spectra the
shift of various bands along with the change of
nitrogen position is remarkable. That means, that the
character of mode does not change while force
constants change significantly. The n(CH) vibration
bands shift markedly along with the nitrogen
position in the aromatic ring. Four ring protons,
present in molecule of each acid, change its position
versus carboxylic group and this brings about the
shift of the appropriate bands. For example, the
band of ns(CH) vibration is present in the spectrum
at 3055, 3042 and 3054 cm21 for picolinic, nicotinic
and isonicotinic acids, respectively (Table 5). In this
region the band connected to n(OH) vibrations

Table 6
The 1800–1500 cm21 region in the IR and Raman experimental and scaled calculated spectra of picolinic, nicotinic and isonicotinic acids

Molecule Experimental B3PW91/6-311þþ G**

21 21
IR (cm ) Raman (cm ) ncalc (cm21) Intensity Raman Activity Assignment, PED%
(A4/Amn)

Picolinic acid 1 1717 s 1692 s 1791 337.8 68.5 84 n(CyO)

1608 m 1608 m 1599 13.1 18.6 61 n2(CyC)P
1595 vs 1598 vs 1582 17.5 2.3 74 n1(CyC)P
Picolinic acid 2 1784 347.8 85.5 84 n(CyO)
1588 1.3 64.1 65 n1(CyC)P
1582 28.3 4.5 71 n2(CyC)P
Picolinic acid 3 1747 329.6 68.3 86 n(CyO)
1565 5.6 67.2 53 n2(CyC)P
1557 17.8 7.2 65 n3(CyC)P
Nicotinic acid 1 1708 s 1754 394.6 77.5 83 n(CyO)
1595 s 1598 63.9 58.9 54 n4(CyC)N
1583 s 1577 11.8 4.9 61 n2(CyC)N
Nicotinic acid 2 1758 387.3 75.6 82 n(CyO)
1598 67.4 61.9 46 n4(CyC)N
1577 16.8 9.17 64 n2(CyC)N
Isonicotinic acid 1712 vs 1690 m 1766 329.6 68.5 84 n(CyO)
1616 w 1617 vs 1606 3.2 41.2 50 n2(CyC)I
1597 w - 1580 25.2 2.2 51 n1(CyC)I
94 P. Koczoń et al. / Journal of Molecular Structure 655 (2003) 89–95

Table 7
The 1500–1300 cm21 region in the IR and Raman experimental and scaled calculated spectra of picolinic, nicotinic and isonicotinic acids

Molecule Experimental B3PW91/6-311þ þG**

IR (cm21) Raman (cm21) ncalc (cm21) IR Intensity Raman Activity Assignment, PED%
(A4/Amn)

Picolinic acid 1 1455 s – 1462 17.5 2.3 42 n3(C ¼ C)pP

1439 m 1441 w 1437 69.5 5.78 43 n4(C ¼ C)pP
1370 vw 1367 471.4 7.9 62 b(OH)
Picolinic acid 2 1462 1.2 2.3 56 n4(CyC)P
1423 14.5 2.7 49 n3(CyC)P
1334 90.6 13.2 67 b(OH)
Picolinic acid 3 1463 8.5 2.7 54 n4(CyC)P
1428 23.5 10.2 45 n3(CyC)P 22 n1(CyC)P
1362 138.6 14.2 71 (OH)
Nicotinic acid 1 1488 m 1454 5.7 3.0 58 n4(CyC)N
1449 w 1414 27.99 2.0 32 n3(CyC)N 30 n1(CyC)N
1370vw 1344 145.9 11.3 68 b(OH)
Nicotinic acid 2 1466 2.8 1.2 33 n4(C ¼ C)pN
1422 24.7 2.4 39 n3(C ¼ C)pN
1338 71 b(OH)
Isonicotinic acid 1478 w – 1488 6.8 4.3 54 n4(CyC)I
1412 vs 1414 w 1408 36.6 1.2 64 n3(CyC)I
1370 vw – 1350 164.5 13.8 70 b(OH)

Other modes contribute to this band.

occur, and wavenumber of this band is sensitive for
position of nitrogen in the aromatic ring as well.
Very intense band assigned to stretching vibrations
n(CyO), changes its position from 1717 cm21 for
picolinic acid down to 1708 cm21 for nicotinic acid.
For isonicotinic isomer this band occurs at
1712 cm21. On the other hand, position of the band
assigned to b(OH) deformation is constant for the
three compounds. In the second analysed region two
of n(CC) bands occur (Table 6). Position of one of
them change: 1608, 1595, 1616 for picolinic, nicotinic
and isonicotinic isomers, respectively. Movement of
the atoms responsible for the second band occurring in
this region is sensitive for the change of nitrogen
position versus carboxylic anion (Table 6).
Two bands occurring in the 1500 –1350 cm21
region responsible for n(CyC) vibrations change
their wavenumber along with change of position of
nitrogen in the aromatic ring. The band for which the
movement is described as n3(CyC) shifts from
1455 cm21 for picolinic acid to 1412 cm21 for
isonicotinic acid. The second band from this region,
described as n4(CyC) is present at 1439, 1488, and
1478 cm21 for picolinic, nicotinic and isonicotinic
acids, respectively.
4. Conclusions
There is not straight regularity in the change of
wavenumbers of the analysed bands along with the
position of the nitrogen atom in the aromatic ring.
That means, electronic charge distribution of the
whole molecule differ depending on the position of
the nitrogen versus carboxylic anion. However, the
vibrational character of the analysed skeletal (CyC)
and (CH) bands is very similar for each isomer, and
difference in electronic charge distribution depends
mainly on change of bond force constants.
Acknowledgements
Presented work was supported by grant of the State
Committee for Scientific Research (KBN; Poland)
No. 6 PO6T 085 21.
 P. Koczoń et al. / Journal of Molecular Structure 655 (2003) 89–95
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