Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy xxx (2014) xxx–xxx
Contents lists available at ScienceDirect
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy journal homepage: www.elsevier.com/locate/saa
Spectroscopic analysis of cinnamic acid using quantum chemical calculations K.S. Vinod a,b, S. Periandy c, M. Govindarajan d,⇑ a
Department of Physics, Indira Gandhi Polytechnic College, Mahe, UT-Puducherry, India Research Scholar, Bharathiar University, Coimbatore, Tamil Nadu, India c Department of Physics, Tagore Arts College, Puducherry, India d Department of Physics, Bharathidasan College for Women, Puducherry, India b
h i g h l i g h t s
g r a p h i c a l a b s t r a c t
Monomer and dimer structures of
cinnamic acid were examined. Spectroscopic analysis was
characterized by FT-IR, FT-Raman and NMR techniques. MSP and Mulliken charge analysis of the compound were studied. HOMO and LUMO energies and UV of the molecule were calculated.
a r t i c l e
i n f o
Article history: Received 17 June 2014 Received in revised form 4 September 2014 Accepted 22 September 2014 Available online xxxx Keywords: HOMO LUMO GIAO Cinnamic acid DFT
a b s t r a c t In this present study, FT-IR, FT-Raman, 13C NMR and 1H NMR spectra for cinnamic acid have been recorded for the vibrational and spectroscopic analysis. The observed fundamental frequencies (IR and Raman) were assigned according to their distinctiveness region. The computed frequencies and optimized parameters have been calculated by using HF and DFT (B3LYP) methods and the corresponding results are tabulated. On the basis of the comparison between computed and experimental results assignments of the fundamental vibrational modes are examined. A study on the electronic and optical properties; absorption wavelengths, excitation energy, dipole moment and frontier molecular orbital energies, were performed by HF and DFT methods. The alternation of the vibration pattern of the pedestal molecule related to the substitutions was analyzed. The 13C and 1H NMR spectra have been recorded and the chemical shifts have been calculated using the gauge independent atomic orbital (GIAO) method. The Mulliken charges, UV spectral analysis and HOMO–LUMO analysis of have been calculated and reported. The molecular electrostatic potential (MEP) was constructed. Ó 2014 Elsevier B.V. All rights reserved.
⇑ Corresponding author. Tel.: +91 9443525988. E-mail address: [email protected] (M. Govindarajan). http://dx.doi.org/10.1016/j.saa.2014.09.098 1386-1425/Ó 2014 Elsevier B.V. All rights reserved.
Please cite this article in press as: K.S. Vinod et al., Spectroscopic analysis of cinnamic acid using quantum chemical calculations, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (2014), http://dx.doi.org/10.1016/j.saa.2014.09.098
2
K.S. Vinod et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy xxx (2014) xxx–xxx
Introduction
O O
H
H O
O H3C
O
CH3
OH
H
H3C
O CH3
Cinnamic acid is (CA) an organic compound with the formula (C6H5CHCHCO2H). It is a white crystalline compound that is slightly soluble in water. It occurs naturally in a number of plants and freely soluble in many organic solvents. CA is widely spread in the plants and possesses wide range of activities [1]. It is also used as precursor for the synthesis of commercially important cinnamic esters. Cinnamic esters are obtained from various plant sources and find application in perfumery, cosmetic industries and in pharmaceutics. This compound is mainly used in anti-tumor and antimicrobial activity [2]. Methoxy substituted cinnamate such as ethyl 3,4,5-trimethoxycinnamate plays an important role in controlling inflammatory diseases [3]. CA and its derivatives are secondary metabolites with antioxidant and antibacterial activities produced by plants in response to stressful conditions, such as infections or wounding [4]. Previous studies have shown the pharmacological properties of cinnamic acid and its derivatives in antioxidant and anti-diabetic activities [5–7]. Cinnamate can act as optical filters or deactivate substrate molecules that have been excited by light for the protection polymers and organic substances. In cosmetic grades, they are used as sunscreen agents to reduce skin damage by blocking UV. Experimental details The molecule CA was purchased from Sigma–Aldrich Chemicals, USA, which is of spectroscopic grade and hence used for recording the spectra as such without any further purification. The FT-IR spectrum of the compound was recorded in Bruker IFS 66V spectrometer in the range of 4000–400 cm1. The spectral resolution is ±2 cm1. The FT-Raman spectrum of the same was also recorded in the same instrument with FRA 106 Raman module equipped with Nd:YAG laser source operating at 1.064 lm line widths with 200 mW power. The spectra are recorded in the range of 4000– 100 cm1 with scanning speed of 30 cm1 min1 of spectral width 2 cm1. The frequencies of all sharp bands are accurate to ±1 cm1. The 13C & 1H NMR spectrum was recorded by spin solve high resolution bench top FT-NMR spectrometer. The operating frequency: 42.5 MHz proton with resolution: 50% line width, 100 ppm [43,44] and the accuracy ensures reliable interpretation of spectroscopic parameters. In the present study, the 13C NMR chemical shifts in the ring are >100 ppm, as they would be expected. The 13C chemical shifts carbonyl carbons vary from 150 to 220 ppm. This depends on the decrease in electron donating or shielding ability of the attached atoms [45]. The C@O groups of carboxylic acids and derivatives are in the range of 150– 185 ppm. NMR spectroscopy technique is throwing new light on organic structure elucidation of much difficult complex molecules. The combined use of experimental and computational tools offers a powerful gadget to interpret and predict the structure of bulky molecules. In this way, the optimized structure of CA is used to calculate the NMR spectra at B3LYP method with 6-311+G(d, p) level using the GIAO method and the chemical shifts of the compound are reported in ppm relative to TMS for 1H and 13C NMR spectra which are presented in Table 7. In the present work, 13C NMR chemical shifts of entire carbons in the ring are below and above 100 ppm, as in the expected regions. The aromatic hydrogen peaks in the rings which are observed experimentally from 7.60 to 7.40 ppm are computed from 8.02 to 7.48 ppm at B3LYP/6311+G(d, p) level of theory. The substituted carbon atoms C12, C13 and C14 peaks are identified at 144.2, 116.3 and 141.5 ppm and also show the confirmation substitution in the molecule. This view shows that, the substitutional groups come into the base molecule and thus chemical property of the ring is changed favor of the substitutions. The shift of the carbons of C2 and C6 and C4and C5 of the ring is found nearly equal. There is no considerable difference of chemical shift between experimental and calculated. Conclusion The FT-IR and FT-Raman spectra were recorded and the detailed vibrational assignments using HF and DFT methods with 6311+G(d, p) and 6-311++G(d, p) basis sets were made for Cinnamic acid. The differences between observed and calculated frequencies are very small for most of fundamentals. Therefore, the results presented in this work for Cinnamic acid indicate that this level of theory is reliable for the prediction of both infrared and Raman spectra of the title compound. The optimized geometrical parameters are calculated and the change in geometry is analyzed. Furthermore, theoretical calculations have been carried out for the thermodynamic properties (heat capacity, entropy and enthalpy) and correlation study for the present compound. It was observed that, these thermodynamic functions were increased with temperature ranging from 100 to 700 K due to the fact that the molecular vibrational intensities increased with temperature. The optimization has been done in order to investigate the energetic behavior and dipole moment of title compound in the gas phase. The electronic excitation in UV–VIS spectra was analyzed and all the transitions are occur in n?p⁄ region. The HOMO and LUMO study for the title
molecule is carried out and find out the energy distribution and energy gap. The calculated Mullikan charge distributions of benzene derivates are compared and the results show that the substitution of the aromatic ring by C2H2 group and COOH leads to a redistribution of electron density. Molecular electrostatic potential MEP contour surfaces give the information about the high potential field and low potential field. 13C NMR and 1H NMR predicts the chemical shift of C and H atom present in the molecule. References [1] S.V. Christine, K.G. Rohan, B.R. Ian, J. Gen. Microbiol. 130 (1984) 2843. [2] N.H. Nam, Y.J. You, Y.D. Kim, H. Hong, H.M. Kim, Y.Z. Ann, Bioorg. Med. Chem. Lett. 11 (2001) 1173. [3] S. Kumar, P. Arya, C. Mukherjee, B.K. Singh, N. Singh, V.S. Prasad, A.K. Ghose, B. Biochem. 44 (2005) 15944. [4] L.G. Korkina, Phenylpropanoids as naturally occurring antioxidants: from plant defense to human health, Cell. Mol. Biol. 53 (2007) 15–25. [5] E.J. Lee, S.R. Kim, J. Kim, Y.C. Kim, Hepatoprotective phenylpropanoids from Scrophularia buergeriana roots against CCl4-induced toxicity: action mechanism and structure-activity relationship, Planta Med. 68 (2002) 407– 411. [6] F. Natella, M. Nardini, M. Felice, C. Scaccini, J. Agric. Food Chem. 47 (1999) 1453–1459. [7] I.M. Liu, F.L. Hsu, C.F. Chen, J.T. Cheng, Br. J. Pharmacol. 129 (2000) 631–636. [8] Gaussian 03, Gaussian Inc., Pitttsburgh, PA, 2003. [9] A.D. Becker, Phys. Rev. A 38 (1988) 3098–3101. [10] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785–790. [11] A.D. Becke, J. Chem. Phys. 98 (1993) 5648–5652. [12] D.C. Young, Computational Chemistry, John Wiley & Sons Inc., New York, 2001. [13] N. Sundaraganesan, S. IIlakiamani, H. Saleem, P.M. Wojiciechowski, D. Michalska, Spectrochim. Acta A 61 (2005) 2995. [14] M.H. Jamróz, Vibrational Energy Distribution Analysis, VEDA 4, Warsaw, 2004. [15] R.I. Dennington, T. Keith, J. Millam, K. Eppinnett, W. Hovell, Gauss View Version, 2003. [16] A. Barcon, M.L. Cote, A.P.J. Brunskill, H.W. Thompson, R.A. Lalancette, Acta Crystallogr. 53 (1997) 1842–1845. [17] L.A. Brown, R.K. Laxman, A.W. Maverick, F.R. Fronczek, Acta Crystallogr. C52 (1996) 95–97. [18] M. Arivazhagan, D. Anitha Rexalin, Spectrochim. Acta 83 (2011) 553–560. [19] M. Govindarajan, M. Karabacak, Spectrochim. Acta 101 (2013) 314–324. [20] R.M. Silverstein, G.C. Bassler, T.C. Morrill, Spectrometric Identification of Organic Compounds, John Wiley, Chichester, 1991. [21] G. Socrates, Infrared and Raman Characteristic Group Frequencies – Tables and Charts, third ed., Wiley, New York, 2001. [22] L.J. Bellamy, The Infrared Spectra of Complex Molecules, Chapman and Hall, London, 1975. [23] N. Puviarasan, V. Arjunan, S. Mohan, Turkey J. Chem. 26 (2002) 323. [24] G. Varsanyi, Vibrational Spectra of Benzene Derivatives, Academic Press, New York, 1969. [25] V. Krishnakumar, R.J. Xavier, Indian J. Pure Appl. Phys. 41 (2003) 597. [26] T.F. Ardyukoiva et al., Atlas of Spectra of Aromatic and Heterocyclic Compounds, Nauka Sib. Otd, Novosibirsk, 1973. [27] J. Mohan, Organic Spectroscopy Principles and Applications, second ed., Narosa Publishing House, New Delhi, 2001. [28] D.N. Sathyanarayana, Vibrational Spectroscopy Theory and Application, New Age International Publishers, New Delhi, 2004. [29] S. Ramalingam, S. Periandy, S. Mohan, Spectrochim. Acta A 77 (2010) 73–81. [30] A.R. Prabakaran, S. Mohan, Indian J. Phys. 63B (1989) 468–473. [31] N. Sundaraganesan, Spectrochim. Acta A 69 (2008) 198–204. [32] L.D.S. Yadav, Organic Spectroscopy, Springer, New Delhi, India, 2004. [33] R.A. Yadav, I.S. Sing, Ind. J. Pure Appl. Phys. 23 (1985) 626. [34] M.A. Palafox, Int. J. Quantum Chem. 77 (2000) 661–684. [35] J.S. Murray, K. Sen, Molecular Electrostatic Potentials, Concepts and 399 Applications, Elsevier, Amsterdam, 1996. [36] E. Scrocco, J. Tomasi, P. Lowdin (Eds.), Advances in Quantum Chemistry, Academic Press, New York, 1978. [37] J. Sponer, P. Hobza, Int. J. Quant. Chem. 57 (1996) 959. [38] K. Fukuli, T. Yonezawa, H. Shingu, J. Phys. Chem. 20 (4) (1952) A722. [39] C.H. Choi, M. Kertesz, J. Phys. Chem. A101 (20) (1997) 3823–3831. [40] S. Gunasekaran, R.A. Balaji, S. Kumaresan, G. Anand, S. Srinivasan, Can. J. Anal. Sci. Spectrosc. 53 (4) (2008) 149–162. [41] I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976. [42] D. Avci, Y. Atalay, M. Sekerci, M. Dincer, Spectrochim. Acta A 73 (1) (2009) 212–217. [43] H.O. Kalinowski, S. Berger, S. Braun, Carbon 13NMR Spectroscopy, John Wiley & Sons, Chichester, UK, 1988. [44] K. Pihlaja, E. Kleinpeter, Carbon-13 NMR Chemical Shifts in Structural and Sterochemical Analysis, VCH Publishers, Deerfield Beach, FL, USA, 1994. [45] P.S. Kalsi, Spectroscopy of Organic Compounds, New Age International, 2004.
Please cite this article in press as: K.S. Vinod et al., Spectroscopic analysis of cinnamic acid using quantum chemical calculations, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (2014), http://dx.doi.org/10.1016/j.saa.2014.09.098
Contents lists available at ScienceDirect
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy journal homepage: www.elsevier.com/locate/saa
Spectroscopic analysis of cinnamic acid using quantum chemical calculations K.S. Vinod a,b, S. Periandy c, M. Govindarajan d,⇑ a
Department of Physics, Indira Gandhi Polytechnic College, Mahe, UT-Puducherry, India Research Scholar, Bharathiar University, Coimbatore, Tamil Nadu, India c Department of Physics, Tagore Arts College, Puducherry, India d Department of Physics, Bharathidasan College for Women, Puducherry, India b
h i g h l i g h t s
g r a p h i c a l a b s t r a c t
Monomer and dimer structures of
cinnamic acid were examined. Spectroscopic analysis was
characterized by FT-IR, FT-Raman and NMR techniques. MSP and Mulliken charge analysis of the compound were studied. HOMO and LUMO energies and UV of the molecule were calculated.
a r t i c l e
i n f o
Article history: Received 17 June 2014 Received in revised form 4 September 2014 Accepted 22 September 2014 Available online xxxx Keywords: HOMO LUMO GIAO Cinnamic acid DFT
a b s t r a c t In this present study, FT-IR, FT-Raman, 13C NMR and 1H NMR spectra for cinnamic acid have been recorded for the vibrational and spectroscopic analysis. The observed fundamental frequencies (IR and Raman) were assigned according to their distinctiveness region. The computed frequencies and optimized parameters have been calculated by using HF and DFT (B3LYP) methods and the corresponding results are tabulated. On the basis of the comparison between computed and experimental results assignments of the fundamental vibrational modes are examined. A study on the electronic and optical properties; absorption wavelengths, excitation energy, dipole moment and frontier molecular orbital energies, were performed by HF and DFT methods. The alternation of the vibration pattern of the pedestal molecule related to the substitutions was analyzed. The 13C and 1H NMR spectra have been recorded and the chemical shifts have been calculated using the gauge independent atomic orbital (GIAO) method. The Mulliken charges, UV spectral analysis and HOMO–LUMO analysis of have been calculated and reported. The molecular electrostatic potential (MEP) was constructed. Ó 2014 Elsevier B.V. All rights reserved.
⇑ Corresponding author. Tel.: +91 9443525988. E-mail address: [email protected] (M. Govindarajan). http://dx.doi.org/10.1016/j.saa.2014.09.098 1386-1425/Ó 2014 Elsevier B.V. All rights reserved.
Please cite this article in press as: K.S. Vinod et al., Spectroscopic analysis of cinnamic acid using quantum chemical calculations, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (2014), http://dx.doi.org/10.1016/j.saa.2014.09.098
2
K.S. Vinod et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy xxx (2014) xxx–xxx
Introduction
O O
H
H O
O H3C
O
CH3
OH
H
H3C
O CH3
Cinnamic acid is (CA) an organic compound with the formula (C6H5CHCHCO2H). It is a white crystalline compound that is slightly soluble in water. It occurs naturally in a number of plants and freely soluble in many organic solvents. CA is widely spread in the plants and possesses wide range of activities [1]. It is also used as precursor for the synthesis of commercially important cinnamic esters. Cinnamic esters are obtained from various plant sources and find application in perfumery, cosmetic industries and in pharmaceutics. This compound is mainly used in anti-tumor and antimicrobial activity [2]. Methoxy substituted cinnamate such as ethyl 3,4,5-trimethoxycinnamate plays an important role in controlling inflammatory diseases [3]. CA and its derivatives are secondary metabolites with antioxidant and antibacterial activities produced by plants in response to stressful conditions, such as infections or wounding [4]. Previous studies have shown the pharmacological properties of cinnamic acid and its derivatives in antioxidant and anti-diabetic activities [5–7]. Cinnamate can act as optical filters or deactivate substrate molecules that have been excited by light for the protection polymers and organic substances. In cosmetic grades, they are used as sunscreen agents to reduce skin damage by blocking UV. Experimental details The molecule CA was purchased from Sigma–Aldrich Chemicals, USA, which is of spectroscopic grade and hence used for recording the spectra as such without any further purification. The FT-IR spectrum of the compound was recorded in Bruker IFS 66V spectrometer in the range of 4000–400 cm1. The spectral resolution is ±2 cm1. The FT-Raman spectrum of the same was also recorded in the same instrument with FRA 106 Raman module equipped with Nd:YAG laser source operating at 1.064 lm line widths with 200 mW power. The spectra are recorded in the range of 4000– 100 cm1 with scanning speed of 30 cm1 min1 of spectral width 2 cm1. The frequencies of all sharp bands are accurate to ±1 cm1. The 13C & 1H NMR spectrum was recorded by spin solve high resolution bench top FT-NMR spectrometer. The operating frequency: 42.5 MHz proton with resolution: 50% line width, 100 ppm [43,44] and the accuracy ensures reliable interpretation of spectroscopic parameters. In the present study, the 13C NMR chemical shifts in the ring are >100 ppm, as they would be expected. The 13C chemical shifts carbonyl carbons vary from 150 to 220 ppm. This depends on the decrease in electron donating or shielding ability of the attached atoms [45]. The C@O groups of carboxylic acids and derivatives are in the range of 150– 185 ppm. NMR spectroscopy technique is throwing new light on organic structure elucidation of much difficult complex molecules. The combined use of experimental and computational tools offers a powerful gadget to interpret and predict the structure of bulky molecules. In this way, the optimized structure of CA is used to calculate the NMR spectra at B3LYP method with 6-311+G(d, p) level using the GIAO method and the chemical shifts of the compound are reported in ppm relative to TMS for 1H and 13C NMR spectra which are presented in Table 7. In the present work, 13C NMR chemical shifts of entire carbons in the ring are below and above 100 ppm, as in the expected regions. The aromatic hydrogen peaks in the rings which are observed experimentally from 7.60 to 7.40 ppm are computed from 8.02 to 7.48 ppm at B3LYP/6311+G(d, p) level of theory. The substituted carbon atoms C12, C13 and C14 peaks are identified at 144.2, 116.3 and 141.5 ppm and also show the confirmation substitution in the molecule. This view shows that, the substitutional groups come into the base molecule and thus chemical property of the ring is changed favor of the substitutions. The shift of the carbons of C2 and C6 and C4and C5 of the ring is found nearly equal. There is no considerable difference of chemical shift between experimental and calculated. Conclusion The FT-IR and FT-Raman spectra were recorded and the detailed vibrational assignments using HF and DFT methods with 6311+G(d, p) and 6-311++G(d, p) basis sets were made for Cinnamic acid. The differences between observed and calculated frequencies are very small for most of fundamentals. Therefore, the results presented in this work for Cinnamic acid indicate that this level of theory is reliable for the prediction of both infrared and Raman spectra of the title compound. The optimized geometrical parameters are calculated and the change in geometry is analyzed. Furthermore, theoretical calculations have been carried out for the thermodynamic properties (heat capacity, entropy and enthalpy) and correlation study for the present compound. It was observed that, these thermodynamic functions were increased with temperature ranging from 100 to 700 K due to the fact that the molecular vibrational intensities increased with temperature. The optimization has been done in order to investigate the energetic behavior and dipole moment of title compound in the gas phase. The electronic excitation in UV–VIS spectra was analyzed and all the transitions are occur in n?p⁄ region. The HOMO and LUMO study for the title
molecule is carried out and find out the energy distribution and energy gap. The calculated Mullikan charge distributions of benzene derivates are compared and the results show that the substitution of the aromatic ring by C2H2 group and COOH leads to a redistribution of electron density. Molecular electrostatic potential MEP contour surfaces give the information about the high potential field and low potential field. 13C NMR and 1H NMR predicts the chemical shift of C and H atom present in the molecule. References [1] S.V. Christine, K.G. Rohan, B.R. Ian, J. Gen. Microbiol. 130 (1984) 2843. [2] N.H. Nam, Y.J. You, Y.D. Kim, H. Hong, H.M. Kim, Y.Z. Ann, Bioorg. Med. Chem. Lett. 11 (2001) 1173. [3] S. Kumar, P. Arya, C. Mukherjee, B.K. Singh, N. Singh, V.S. Prasad, A.K. Ghose, B. Biochem. 44 (2005) 15944. [4] L.G. Korkina, Phenylpropanoids as naturally occurring antioxidants: from plant defense to human health, Cell. Mol. Biol. 53 (2007) 15–25. [5] E.J. Lee, S.R. Kim, J. Kim, Y.C. Kim, Hepatoprotective phenylpropanoids from Scrophularia buergeriana roots against CCl4-induced toxicity: action mechanism and structure-activity relationship, Planta Med. 68 (2002) 407– 411. [6] F. Natella, M. Nardini, M. Felice, C. Scaccini, J. Agric. Food Chem. 47 (1999) 1453–1459. [7] I.M. Liu, F.L. Hsu, C.F. Chen, J.T. Cheng, Br. J. Pharmacol. 129 (2000) 631–636. [8] Gaussian 03, Gaussian Inc., Pitttsburgh, PA, 2003. [9] A.D. Becker, Phys. Rev. A 38 (1988) 3098–3101. [10] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785–790. [11] A.D. Becke, J. Chem. Phys. 98 (1993) 5648–5652. [12] D.C. Young, Computational Chemistry, John Wiley & Sons Inc., New York, 2001. [13] N. Sundaraganesan, S. IIlakiamani, H. Saleem, P.M. Wojiciechowski, D. Michalska, Spectrochim. Acta A 61 (2005) 2995. [14] M.H. Jamróz, Vibrational Energy Distribution Analysis, VEDA 4, Warsaw, 2004. [15] R.I. Dennington, T. Keith, J. Millam, K. Eppinnett, W. Hovell, Gauss View Version, 2003. [16] A. Barcon, M.L. Cote, A.P.J. Brunskill, H.W. Thompson, R.A. Lalancette, Acta Crystallogr. 53 (1997) 1842–1845. [17] L.A. Brown, R.K. Laxman, A.W. Maverick, F.R. Fronczek, Acta Crystallogr. C52 (1996) 95–97. [18] M. Arivazhagan, D. Anitha Rexalin, Spectrochim. Acta 83 (2011) 553–560. [19] M. Govindarajan, M. Karabacak, Spectrochim. Acta 101 (2013) 314–324. [20] R.M. Silverstein, G.C. Bassler, T.C. Morrill, Spectrometric Identification of Organic Compounds, John Wiley, Chichester, 1991. [21] G. Socrates, Infrared and Raman Characteristic Group Frequencies – Tables and Charts, third ed., Wiley, New York, 2001. [22] L.J. Bellamy, The Infrared Spectra of Complex Molecules, Chapman and Hall, London, 1975. [23] N. Puviarasan, V. Arjunan, S. Mohan, Turkey J. Chem. 26 (2002) 323. [24] G. Varsanyi, Vibrational Spectra of Benzene Derivatives, Academic Press, New York, 1969. [25] V. Krishnakumar, R.J. Xavier, Indian J. Pure Appl. Phys. 41 (2003) 597. [26] T.F. Ardyukoiva et al., Atlas of Spectra of Aromatic and Heterocyclic Compounds, Nauka Sib. Otd, Novosibirsk, 1973. [27] J. Mohan, Organic Spectroscopy Principles and Applications, second ed., Narosa Publishing House, New Delhi, 2001. [28] D.N. Sathyanarayana, Vibrational Spectroscopy Theory and Application, New Age International Publishers, New Delhi, 2004. [29] S. Ramalingam, S. Periandy, S. Mohan, Spectrochim. Acta A 77 (2010) 73–81. [30] A.R. Prabakaran, S. Mohan, Indian J. Phys. 63B (1989) 468–473. [31] N. Sundaraganesan, Spectrochim. Acta A 69 (2008) 198–204. [32] L.D.S. Yadav, Organic Spectroscopy, Springer, New Delhi, India, 2004. [33] R.A. Yadav, I.S. Sing, Ind. J. Pure Appl. Phys. 23 (1985) 626. [34] M.A. Palafox, Int. J. Quantum Chem. 77 (2000) 661–684. [35] J.S. Murray, K. Sen, Molecular Electrostatic Potentials, Concepts and 399 Applications, Elsevier, Amsterdam, 1996. [36] E. Scrocco, J. Tomasi, P. Lowdin (Eds.), Advances in Quantum Chemistry, Academic Press, New York, 1978. [37] J. Sponer, P. Hobza, Int. J. Quant. Chem. 57 (1996) 959. [38] K. Fukuli, T. Yonezawa, H. Shingu, J. Phys. Chem. 20 (4) (1952) A722. [39] C.H. Choi, M. Kertesz, J. Phys. Chem. A101 (20) (1997) 3823–3831. [40] S. Gunasekaran, R.A. Balaji, S. Kumaresan, G. Anand, S. Srinivasan, Can. J. Anal. Sci. Spectrosc. 53 (4) (2008) 149–162. [41] I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976. [42] D. Avci, Y. Atalay, M. Sekerci, M. Dincer, Spectrochim. Acta A 73 (1) (2009) 212–217. [43] H.O. Kalinowski, S. Berger, S. Braun, Carbon 13NMR Spectroscopy, John Wiley & Sons, Chichester, UK, 1988. [44] K. Pihlaja, E. Kleinpeter, Carbon-13 NMR Chemical Shifts in Structural and Sterochemical Analysis, VCH Publishers, Deerfield Beach, FL, USA, 1994. [45] P.S. Kalsi, Spectroscopy of Organic Compounds, New Age International, 2004.
Please cite this article in press as: K.S. Vinod et al., Spectroscopic analysis of cinnamic acid using quantum chemical calculations, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (2014), http://dx.doi.org/10.1016/j.saa.2014.09.098
