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Asian Journal of Spectroscopy, 11,3&4, 2007, 169-172 Spectroscopic and Intra Molecular Studies of Pharmaceutically Important Benzoic Acid and its Amino Substitutents
Y.P.Singha, R.A.Singhb and Ratnesh Dasc
a
Department of Physics, Govt. Womenâ€™s Polytechnic College, Sagar (MP), INDIA 470001.E-mail: Y_P_S_2k@Yahoo.com b Department of Physics, Dr. H.S.Gour University, Sagar (MP), INDIA, 470001 c Department of Chemistry, Dr. H.S.Gour University, Sagar (MP), INDIA, 470001, E-mail: ratnesh_das@brea

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Benzoic Acid and its Amino Substitutents

a

Department of Physics, Govt. Women’s Polytechnic College, Sagar (MP), INDIA

470001.E-mail: Y_P_S_2k@Yahoo.com

b

Department of Physics, Dr. H.S.Gour University, Sagar (MP), INDIA, 470001

c

Department of Chemistry, Dr. H.S.Gour University, Sagar (MP), INDIA, 470001,

E-mail: ratnesh_das@breakthru.com

ABSTRACT

The vibrational absorption spectra of Benzoic Acid’s Monomer molecules and its amino

substitutents have been studied using GF matrix and AM1 method. Assuming C s point symmetry,

vibrational assignments for the observed frequencies have been proposed. The spectra exhibit

distinct features originating from low frequency vibrational modes caused by intra-molecular

motion. Normal modes have been calculated and an assignment of the observed spectra has been

proposed. Experimental frequencies are compared with those obtained by G.F.Matrix and AM1

method.

Keywords : Benzoic Acid,o-, m-, p- Amino Benzoic Acid, FTIR Spectra, AM1, G.F.Matrix

INTRODUCTION

Carboxylic acids (RCOOH) are a common and important functional group and provide

the point of success to the carboxylic acids derivatives (acetyl chlorides, esters, amides etc.) and

therefore, it has been extensively studied by spectroscopic methods. Spectroscopist's interest has

been concerned with structure and vibrational frequencies.

The aim of the present study is a IR spectroscopic analysis of Benzoic Acid (BA), which

have found considerable attention in the literature1-8. We compared experimental results with

calculated frequencies of BA using force matrix method and AM1, PM3 and G.F. Matrix method.

These methods were able to account breadth of spectrum as well as description of vibrational

modes to encourage the application of a similar procedure to a larger and more complex group.

STRUCTURE AND GEOMETRY OF BENZOIC ACID

aniline and toluene, the geometry parameters were transferred. Cartesian coordinates of the

molecules under investigation were calculated on the basis of geometrical parameters as shown

in Table 1

EXPERIMENTAL

Benzoic acid was purchased from Sigma Chemical Co (USA). Benzoic acid forms a

white to off white crystalline powder with melting point of 159 c. I.R. Spectrum has been

recorded in the liquid phase in the range 400-4000cm-1 on Perkin-Elmer spectrometer Model

397. Preparation of KBr Pallets: A small amount of finally grounded solid sample was intimately

mixed with about 100 times or more than its weight of Potassium bromide powder. The finally

grounded mixture was than pressed under very high pressure in a press (about 10/cm2) to form a

small pallet (about 1-2 mm thick and 1cm in diameter).

The accuracy of the measurements was estimated to be within 3cm-1 and the resolution

was better than 2cm-1 through the entire range for both the spectra.

G tt’= Σ3Ni=1 (B ti B t’i’) 1/ mi where t, t’ = 1,2,3,……, 3N-6

In which mi is the mass of the atom to which the subscript I refers and Bti , Bt’i’ are

constants determined by geometry of molecule.

Internal coordinate St are related with Cartesian displacement coordinate ξi as :

St = Σ 3Ni=1 Bti ξi where t = 1,2,3….., 3N-6

On solving G.F. matrix for any atom α is obtained as:

G tt’= Σ3N α =1 μ α St α . St’ α

Where dot represents the scalar product of two vectors and μ α = 1/m α , the reciprocal of the

mass of atom α

The AM1 semi empirical approaches was performed as implemented in MOPAC

10

program and the PRECISE keywords were used. We have transformed the harmonic force

fields, determined initially in the Cartesian coordinates, were transformed to the force fields in

the internal local coordinates. The force fields obtained were used to calculate the potential

energy distribution (PED)11. Contributions greater than 10% are given.

We had employed a very large basis set for the computational of the frequencies. First

infrared frequencies were calculated for the BA ( Cs Symmetry) at the AM1 and G F Matrix level

of theory. We can get information from computational vibrational spectra only when we compare

it with experimental spectrum.Our results are given in table 2. Due to anharmonicity, the

harmonic vibrational frequencies were found to be lowered by1 to 3% in GF Matrix method

except AM1 method.

Benzoic acid contains 15 atoms so that it has 39 normal modes. The calculated normal modes are

distributed among 27 a΄ and 12 a΄΄ species of Cs symmetry group. The table 2 also shows that

PED contributions for 39 normal modes. These assignments are partly based on the calculated

frequencies. As the table 2 is self-explanatory, we shall discuss here only some important points.

OH Stretch: Experimental OH stretch band frequency for BA is 3507 cm −1 which was shifted

by 97 cm −1 as reported by Antony et al13 and which is also higher than those observed by

others7,16. Theoretically calculated frequencies by G.F. and AM1 are 3579.2 cm −1 and 3627.6 cm

−1

, respectively.

CH3 s-stretch: As presented in table2, experimental CH3 s-stretch frequency for BA is 2987 cm

−1

. Antony et al13 observed this frequency for benzoic acid at 2943 cm −1 . Calculated frequencies

by G.F. and AM1 are 3010.9 cm −1 and 3172.0 cm −1 respectively.

C=O stretch: experimental observed frequencies for this bands is 1823 cm −1 for BA, which is

higher than the calculated frequencies . Antony et al13 observed this frequency for benzoic acid at

1752 cm −1 . Theoretically calculated frequencies by G.F. and AM1 are 1716.5 cm −1 and 1726.2

cm −1 respectively.

O-H Bend: Our observations for this bend is 1328BA. Antony et al13 observed this frequency for

benzoic acid at 1381 cm −1 . Trout et al observed 1328 frequency for COO symmetric stretch, so

our assignment was totally reversed by this one. Computationally calculated frequencies by G.F.

and AM1 are 1311.5 cm −1 and 1441.9 cm −1 respectively.

C-O stretch: Experimental frequency for BA is 1228 cm −1 respectively. Antony et al13 did not

observed this frequency for benzoic acid. Theoretically calculated frequencies by G.F. and AM1

are 1243.8 cm −1 and 1435.7 cm −1 respectively.

O-C-O Deformation: We observed this bend frequency at 668 cm −1 for BA respectively which is

comparative to others14,16 . Theoretically calculated frequencies by G.F. and AM1 are 657.7 cm −1

and 646.3 cm −1 respectively.

Torsion: Experimental observed frequency for this bend for BA is 591 cm −1 . Antony et al15

observed this frequency for benzoic acid at 444 cm −1 . Computationally calculated frequencies by

G.F. and AM1 are 593.4 cm −1 and 571.9 cm −1 respectively.

NH 2 Group Modes

The number of internal vibrations for a group is given by 3m-3, where m is the number of

atoms in the group. Thus NH 2 has 6 modes of vibrations. These modes are as : two stretching

vibrations ( one symmetric and one asymmetric) both belonging to a’ species, two angle

deformations (scissoring and rocking), one out-of-plane wagging of NH 2 and one torsion

vibration of NH 2 .

There are three major differences between the C-H and N-H stretching frequencies. First,

the force constant for N-H stretching is stronger, there is a larger dipole moment associated with

the N-H bond, and finally, the N-H bond is usually involved in hydrogen bonding. The stronger

force constant leads to a higher frequency for absorption. The N-H stretching frequency is

usually observed from 3500-3200 cm-1. The larger dipole moment leads to a stronger absorption

and the presence of hydrogen bonding has a definite influence on the band shape and frequency

position.

The NH 2 stretching modes appear in the region 3500 – 3100 cm −1 and the asymmetric

19

component has slightly higher magnitude than the symmetric component. D.N.Singh

observed asymmetric modes at 3465 cm −1 and symmetric mode at 3360 cm −1 . However,

A.K.Tiwari 20 observed them at 3449 cm −1 and 3367 cm −1 respectively.

He observed in-plane bending and rocking mode at 1630 cm −1 and 1055 cm −1

respectively. A.K.Tiwari19 got in-plane bending mode at 1621 cm −1 and rocking mode at 952

cm −1 . D.N.Singh 20 observed wagging vibration at 592 cm −1 and he didn’t got

torsion mode. A.K.Tiwari19 observed these vibrations at 626 cm −1 and 274 cm −1 respectively.

In present study we get frequencies for them as shown in table 3.

COOH Group Modes

In the parent molecule benzene if one of the hydrogen atom is replaced by a COOH

group, nine more normal modes would appear. They are as:- O-H Stretching, C-O Stretching,

C=O Stretching, in-plane-rocking, in-plane bending of C-O, in-plane-bending of C=O, in-

plane-bending of OH, out-of-plane wagging, and out-of-plane torsion.. J. Antony et al13

studied vibrational spectra of benzoic acid and got C=O Stretching at 1745 cm −1 , C-O

stretching at 1050 cm −1 , C-O in-plane bending at 594 cm −1 , C=O in-plane bending at 1804

cm −1 , OH stretch at 3785 cm −1 , rocking mode at 554 cm −1 , torsion mode at 594 cm −1 and

wagging mode at 441 cm −1 . Florio et aI 15

observed C=O Stretching at 1752 cm −1 , C-O

stretching at 1347 cm −1 , C-O in-plane bending at 628 cm −1 , OH stretch at 3785 cm −1 ,

rocking mode at 628 cm −1 , and wagging mode at 160 cm −1 . In present study we get

frequencies as shown in table 4.

CONCLUSIONS

geometry and vibrational frequencies of the Benzoic acid and its amino substitutents are

presented in this paper and compared with infrared spectra. The calculated geometries and

frequencies agree well with the experimental ones, but there are some differences between

frequencies mainly due to intermolecular interactions, anharmonicity and computational basis

set.

ACKNOWLEDGEMENTS

Bhopal and Head, Department of Physics, Dr. H.S.Gour University, Sagar (MP), India and

Central Drug Research Institute, Lucknow, India for IR spectra, Hypercube Inc for providing

Hyperchem Package 7 for molecular modeling.

Table 1 Assumed Bond Length and Bond angle in Benzoic and Amino Benzoic Acids.

Bond By DFT Experime By MOPAC Bond Angle By DFT Experime By MOPAC

Method 18 ntal Calculation Method 18 ntal Calculation

O2 – H6 1.00 0.98 1.06 C7 O2 H6 110.27 106.00

C 7 – O1 1.230 1.26 1.19 O1 C 7 O 2 123.26 122.2 122.81

C7 – O2 1.323 1.27 1.21 O 2 C 7 C1 114.50 118.0 118.10

C 7 – C1 1.486 1.48 1.10 C1 C 7 O1 122.24 122.0 121.42

C1 – C 2 1.400 1.39 1.40 C 7 C1 C 2 121.40 118.0 121.53

C2 – C3 1.391 1.38 1.39 C 6 C1 C 7 119.90 119.9 119.96

C3 – C 4 1.395 1.37 1.40 C 6 C1 C 7 118.70 118.8 119.96

C 4 – C5 1.395 1.38 1.39 C1 C 2 C 3 119.86 120.1 120.00

C5 – C6 1.390 1.40 1.40 C2 C3C 4 120.02 119.9 119.98

C 6 – C1 1.400 1.39 1.39 C3C 4 C5 120.15 120.3 120.02

C 2 – H1 1.082 0.79 1.10 C 4 C5C6 119.98 119.7 119.98

C3 – H2 1.084 0.96 1.10 C5C6C7 120.02 119.8 119.99

C4 – H3 1.084 0.91 1.10 C1 C 2 H1 119.48 119 120.00

C–N 1.103 1.10 1.11 H2 C3C 4 120.07 119 120.00

N-H 1.154 1.12 1.13 119.91 118 119.50

C3C 4 H3

119.94 118 119.63

H3C 4 C5

120.09 119 120.01

C3C5H 4

119.93 120 119.96

H 4 C5C6 121.12 121 121.23

C5C6H5 118.86 118 118.63

H 5 C 6 C1 119.98 119 119.99

CNH

148.95 150 147.95

HNH

103 95.6

Table 2 Experimental and Calculated Frequencies and Potential Distribution in C 6 H 5 COOH

Assignme G F Matrix Frequencies

nt Experimental (in cm −1 )

Frequencies

Frequencies PED and Mode AM1

−1

−1

(in cm ) (in cm )

2 3217 3210.6 CH str 3188.2

3 3130 3118.8 CH str 3190.2

4 3100 3111.5 CH str 3102.2

5 3087 3072.4 CH str 3175.7

6 2987 3010.9 CH str 3172.0

7 1823 1716.5 C=O str 1786.2

8 1696 1648.1 CC ring 1921

deformation

9 1585 1561.4 C-C str 1765.5

10 1499 1518.7 COH bnding 1638.6

12 1328 1311.5 OH bending 1441.9

13 1228 1243.8 C-O str 1435.7

14 1292 1312.3 CCh bending 1378.9

15 1280 1277.3 O-H bend 1359.0

16 1186 1171.4 CH ib 1314.7

17 1179 1192.5 COH bending 1229.4

18 1129 1134.6 Ring id+C-O str 1198.3

19 1074 1063.1 Ring CCH 1177.5

bending

20 1029 1011.1 Ring id + CC str 1168.0

21 1000 1013.9 CH od 1089.4

22 808 801.3 CH od 796.5

23 668 652.7 OCO deform 646.3

24 600 587.3 Ring CCC 536.8

bending

25 548 525.6 COH bending 509.9

26 420 412.1 C-O bending 409.6

27 317 310.5 C=O bending 286.0

Assig Experiment G F Matrix Frequencies

nment al (in cm −1 )

Frequencies Frequenci PED and Mode AM1

es

(in cm −1 ) (in cm −1 )

29 970 967.3 CC wagging 995.6

30 929.5 rocking 971.8

31 935 937.6 CC wagging 894.5

32 850 844.1 Ring CCH 886.3

33 812 801.9 Ring CCH bend 825.9

34 709 719.8 C=O o.p.bend 723.6

35 664 657.1 Ring CCH bend 610.2

36 613 609.3 torsion 611.9

37 591 593.4 torsion 571.92

38 190 199.4 wagging 150.6

39 57.6 twisting 44.0

Mode of Vibration o-Amino Benzoic Acid m-Amino Benzoic Acid p-Amino Benzoic

(in cm −1 ) (in cm −1 ) Acid (in cm −1 )

N-H Asymmetric 3622 (E), 3601.6(GF) 3472(E), 3490.1(GF) 3509(E), 3521.3(GF)

Stretching 3530.9(M) 3492.4(M) 3512.2(M)

a’ CN-H Symmetric 3325(E), 3342.9(GF) 3225(E), 3207.6(GF) 3462(E), 3487.2(GF)

Stretching 3530.9(M) 3464.6(M) 3490.0(M)

NH 2 In-Plane 1156(E), 1162.3(GF) 1110(E), 1123.5(GF) 1132(E), 1140.1(GF)

Bending 1219.5(M) 1217.7(M) 1143.9(M)

NH 2 Rocking 536(E), 527.1(GF) 541(E), 531.3(GF) 523(E), 529.3(GF)

558.1(M) 537.2(M) 539.3(M)

440.5(M) 497.4(M) 380.2(M)

Torsion 279(E), 284.7(GF) 281(E), 280.2(GF) 291(E), 300.1(GF)

281.7(M) 251.2(M) 326.0(M)

E :- Experimental frequencies

GF:- Theoretical frequencies calculated by GF Matrix method

M:- Theoretical frequencies calculated by MOPAC method

Vibration (cm −1 ) Acid (cm −1 ) Acid (cm −1 ) Acid (cm −1 )

O-H Stretching 3389 (E) 3338(E) 3420(E) 3400(E)

3379.2(GF) 3315.6(GF) 3431.1(GF) 3429.1(GF)

a’ 3427.3(M) 3427.8(M) 3427.5(M) 3431.7(M)

C-O Stretching 1823(E) 1856(E) 1845(E) 1793(E)

1818.1(GF) 1846.3(GF) 1863.2(GF) 1728.2(GF)

1821.0(M) 1959.2(M) 2075.5(M) 1737.3(M)

C=O Stretching 1696(E) 1590(E) 1603(E) 1657(E)

1716.5(GF) 1581.5(GF) 1621.1(GF) 1631.1(GF)

2076.2(M) 1549.9(M) 1551.2(M) 1600.7(M)

Bending C-O 420(E) 440(E) 450(E) 441(E)

412.1(GF) 421.5(GF) 431.3(GF) 411.2(GF)

409.6(M) 414.5(M) 437.2(M) 416.4(M)

Bending C=O 317(E) 351(E) 335(E) 366(E)

310.5(GF) 362.4(GF) 338.2(GF) 371.1(GF)

200.0(M) 259.5(M) 334.3(M) 377.5(M)

Bending OH 1328(E) 1360(E) 1310(E) 1337(E)

1343.8(GF) 1358.9(GF) 1321.6(GF) 1332.3(GF)

1435.7(M) 1355.5(M) 1435.5(M) 1331.7(M)

a” 657.1(GF) 619.3(GF) 579.4(GF) 706.2(GF)

610.2(M) 637.1(M) 579.5(M) 754.3(M)

Wagging 288(E) 293(E) 293(E) 291(E)

293.4(GF) 284.7(GF) 285.2(GF) 300.1(GF)

271.9(M) 281.7(M) 266.7(M) 326.0(M)

Torsion 709(E) 758(E) 789(E) 768(E)

719.8(GF) 751.8(GF) 751.7(GF) 786.1(GF)

723.6(M) 753.5(M) 744.1(M) 875.3(M)

E :- Experimental frequencies

GF:- Theoretical frequencies calculated by GF Matrix method

M:- Theoretical frequencies calculated by MOPAC method

REFRENCES

1. WWW.Chemicalland21.com, Nov.(2005).

2. Foye’s principle of medicinal Chemistry, 5th edition, Lippincott Williams and Wilkins,

New York, (2002)

3. J.H.S.Green, W.kynaston and L.S.Lindsey, Spectrochim Acta A; 17, 486, (1961).

4. J.H.S.Green, D.J.Harrison, Spectrochim Acta ; 26A,1925, (1970).

5. J.H.S.Green , Spectrochim Acta ; 33A, 575, (1977).

6. Y. Kim and K.Machida, Spectrochim Acta, 42A, 8, 881, (1986)

7. A.Theoret, Spectrochim Acta A, 27, 11, (1971).

8. V.K.Rastogi, M.P.Rajpoot and S.N.Sharma; Ind. J. Phy; 58B, 311 (1984).

9. E.B.Wilson ,J C Decius and P C Cross, Molecular Vibrations, Mc Graw-Hill Book Co.,

(1955)

10. Win MOPAC- Molecular Orbital Program, Fujitsu Limited, (1997)

11. G. Keresztury and G. Jalsovsky, J. Mol. Structure, 304, (1971)

12. J.M. Bakker, G. Meyer, M. Kabelac and M.S. de Vries, Phy Chem Chem Phys, 6, 2810,

(2004).

13. J. Antony, G.V.Helden, G. Meijer and B. Achmidt, J. of Chemical Physics,122,

(2005).

14. G.M. Florio, E.L. Sibert and T.S. Zwier; Faraday Discuss, 118, 315, (2001).

15. G.M.Florio, T.S.Zweir and E.L.Sibert, J. Chem. Phys; 118, 1735, (2003).

16. K.C.Light and T. Carrington; Adv. Chem. Phys; 114, 263, (2000).

17. R.Glaser, J. Org. Chem; 66, 771, (2001).

18. M.J. Wojick, K.Szczepenek and M. Boczar, Int. J. Mol. Sci; 4, 422, (2003).

19. D.N.Singh, Ph.D. Thesis, Banaras Hindu University, Banaras, India, (1980).

20. A.K.Tiwari, Ph.D.Thesis, Dr. H.S.Gaur University,Sagar, India (2004).

.

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