Molecular structure and vibrational spectra of phenobaraitone by density functional theory and ab initio hartree-Fock calculations

doi:10.1007/s11458-011-0255-4

Front Chem Chin

2011, Vol. 6

Issue (4) : 358-366 https://doi.org/10.1007/s11458-011-0255-4

RESEARCH ARTICLE

Molecular structure and vibrational spectra of phenobaraitone by density functional theory and ab initio hartree-Fock calculations

Ruizhou ZHANG¹(

), Xiaohong LI¹, Xianzhou ZHANG²

1. College of Physics and Engineering, Henan University of Science and Technology, Luoyang 471003, China; 2. College of Physics and Information Engineering, Henan Normal University, Xinxiang 453007, China

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Abstract

Quantum chemistry calculations have been performed using Gaussian03 program to compute optimized geometry, harmonic vibrational frequency along with intensities in IR and Raman spectra at RHF/6-31++G** and B3LYP/6-31++G** levels for phenobarbitone (C₁₂H₁₂N₂O₃) in the ground state. The scaled harmonic vibrational frequencies have been compared with experimental FT-IR and FT-Raman spectra. Theoretical vibrational spectra of the title compound were interpreted by means of potential energy distributions (PEDs) using MOLVIB program. A detailed interpretation of the infrared spectra of the title compound is reported. On the basis of the agreement between the calculated and observed results, the assignments of fundamental vibrational modes of phenobarbitone were examined and some assignments were proposed. The theoretical spectrograms for FT-IR and FT-Raman spectra of the title compound have been constructed.

Keywords phenobarbitone vibrational spectra HF ab initio calculation density functional theory (DFT)

Corresponding Author(s): ZHANG Ruizhou,Email:lorna639@126.com

Issue Date: 05 December 2011

Cite this article:

Ruizhou ZHANG,Xiaohong LI,Xianzhou ZHANG. Molecular structure and vibrational spectra of phenobaraitone by density functional theory and ab initio hartree-Fock calculations[J]. Front Chem Chin, 2011, 6(4): 358-366.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-011-0255-4
https://academic.hep.com.cn/fcc/EN/Y2011/V6/I4/358

Fig.1 (a) The atom numbering scheme of phenobarbitone; (b) the optimized structure of phenobarbitone

Tab.1 Optimized geometrical parameters of phenobarbitone with 6-31++G** basis set

Tab.2 The selected hydrogen bond lengths (?) and bond angles (° ) calculated by RHF/6-31+ + G** method

Tab.3 Atomic charges for optimized geometry of phenobarbitone

Tab.4 Calculated and experimental fundamental frequencies (cm) for phenobarbitone

Fig.2 (a) The experimental FT-IR vibrational spectra of phenobarbitone; (b) the experimental FT-Raman vibrational spectra of phenobarbitone

Fig.3 (a) The calculated FT-IR vibrational spectra of phenobarbitone by B3LYP method; (b) the calculated FT-Raman vibrational spectra of phenobarbitone by B3LYP method

Tab.5 Theoretically computed energies (a.u.), zero-point vibrational energies (kcal·mol), rotational constants (GHz), entropies (cal·mol·K) and dipole moment () for the title compound with 6-31++G** basis set

1	Brown, M. L.; Brown, G. B.; Brouillette, W. J., J. Med. Chem. 1997, 40, 602–607 doi: 10.1021/jm960692v pmid:9046351
2	Williams, P. P., Acta Crystallogr. B 1974, 30, 12
3	Gunasekaran, S.; Thilak Kumar, R.; Periyanayagasamy, V.; Raihana, M. P.; Asian J. Chem. 2005, 17, 1211
4	Gunasekaran, S.; Ponnambalam, U.; Muthu, S.; Ponnusamy, S.; Asian, J., Chem. 2004, 16, 1513
5	Gunasekaran, S.; Ponnambalam, U.; Muthu, S., Acta Ciencia Indica XXX. 2004, 1, 15
6	Gunasekaran, S.; Ponnambalam, U.; Muthu, S.; Mariappan, L.Asian. J. Phys. 2003, 16, 51
7	Gunasekaran, S.; Shankari, G.; Ponnusamy, S., Spectrochimica Acta Part A. 2005, 61, 117-127 doi: 10.1016/j.saa.2004.03.030
8	Gunasekaran, S.; Thilak Kumar, R.; Ponnusamy, S., Spectrochimica Acta Part A. 2006, 65, 1041-1052 doi: 10.1016/j.saa.2006.01.037
9	Korth, H. G.; de Heer, M. I.; Mulder, P., J. Phys. Chem. 2002, 106, 8779
10	Chowdhury, P. K., J. Phys. Chem. A 2003, 107, 5692-5696 doi: 10.1021/jp034538d
11	Chis, V., Chem. Phys. 2004, 300, 1-11 doi: 10.1016/j.chemphys.2004.01.003
12	Asensio, A.; Kobko, N.; Dannenberg, J. J., J. Phys. Chem. A 2003, 107, 6441-6443 doi: 10.1021/jp0344646
13	Jensen, F., Introduction to Computational Chemistry, Wiley, New York , 1999.
14	Rauhut, G.; Pulay, P., J. Phys. Chem. 1995, 99, 3093-3100 doi: 10.1021/j100010a019
15	Sinha, P.; Boesch, S. E.; Gu, C.; Wheeler, R. A.; Wilson, A. K., J. Phys. Chem A. 2004, 108, 9213-9217 doi: 10.1021/jp048233q
16	Scott, A. P.; Radom, L., J. Phys. Chem. 1996, 100, 16502-16513 doi: 10.1021/jp960976r
17	Kolev, T. M.; Stamboliyskaya, B. A.,Spectrochimica acta Part A . 2002, 58, 3127
18	Pfeiffer, M.; Baier, F.; Stey, T.; Leusser, D.; Stalke, D.; Engels, B.; Moigno, D.; Kiefer, W., J. Mol. Model. 2000, 6, 299-311 doi: 10.1007/PL00010731
19	Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A., Gaussian ’03, Revision C. 01, Gaussian, Inc., Wallingford, CT , 2004
20	Becke, A. D., J. Chem. Phys. 1993, 98, 5648 doi: 10.1063/1.464913
21	Lee, C.; Yang, W.; Parr, R. G., Phys. Rev. B 1988, 37, 785-789 doi: 10.1103/PhysRevB.37.785
22	Becke, B. D., Phys. Rev. B 1988, 38, 3098
23	Vosko, S. H.; Wilk, L.; Nusair, M., Can. J. Phys. 1980, 58, 1200-1211 doi: 10.1139/p80-159
24	Fast, P. L.; Corchado, J.; Sanchez, M. L.; Truhlar, D. G., J. Phys. Chem. A 1999, 103, 3139-3143 doi: 10.1021/jp9900382
25	Sundius T., MOLVIB: A program for harmonic force field calculations, QCPE program No. 807, 2002
26	Sundius, T., Vib. Spectrosc. 2002, 29, 89-95 doi: 10.1016/S0924-2031(01)00189-8
27	Keresztury, G.; Holly, S.; Varga, J.; Besenyei, G.; Wang, A. Y.; Durig, J. R., Spectrochimica Acta Part A. 1993, 49, 2007-2026 doi: 10.1016/S0584-8539(09)91012-1
28	Keresztury, G.; Chalmers, J. M.; Griffith, P. R., RamanSpectroscopy: Theory in Handbook of Vibrational Spectroscopy, vol. 1, John Wiley & Sons Ltd. , 2002, p127
29	Coates, J., in: Meyers R.A. (Ed.), Interpretation of Infrared Spectra, A Practical Approach, John Wiley and Sons Ltd., Chichester , 2000, p235
30	Roeges, N. P. G., A Guide to Complete Interpretation of Infrared Spectra of Organic Structures, Wiley, New York , 1994, p74
31	Socrates, G., Infrared Characteristic Group Frequencies, John Wiley, New York , 2000, p158
32	Chithambarathanu, T.; Umayourbaghan, V.; Krishnakumar, V., Indian J.Pure Appl. Phys . 2003, 41, 844
33	Nakkeeran, C., DissertationTip, Bharathidasan University, Tiruchirappalli, Tamil Nadu, India, 1997.
34	Parasuraman, M., DissertationTip, University of Madras, Chennai, India, 2001.
35	Krishnakumar, V.; John Xavier, R., Indian, J.Pure Appl. Phys. 2003, 41, 597
36	Mohan, S.; Sundaraganesan, N.; Mink, J., Spectrochimica Acta Part A. 1991, 47, 1111-1115 doi: 10.1016/0584-8539(91)80042-H
37	Panicker, C. Y.; Varghese, H. T.; Philip, D. P.; Nogueira, H. I. S.; Kastkova, K., Spectrochimica Acta Part A. 2007, 67, 1313-1320 doi: 10.1016/j.saa.2006.09.042
38	Barthes, M.; De Nunzio, G.; Riber, G., Synth. Met. 1996, 76, 337-340 doi: 10.1016/0379-6779(95)03484-2
39	Xavier Jesu Raja, S.; William, A.; Gunasekaran, S., Orient J. Chem. 1994, 10, 3
40	Marshell, J.; Gunasekaran, S.,Indian J. Phys. B 1996, 70, 505
41	Sato, H.; Dybal, J.; Murakami, R.; Noda, I.; Ozaki, Y., J. Mol. Struct. 2005, 35, 744

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