Abstract
The analyses of possible conformations, molecular structures, vibrational and electronic properties of 2-(methylthio)nicotinic acid molecule, C7H7NO2S, with the synonym 2-(methylsulfanyl)nicotinic acid have been first presented theoretically. At the same time, FT-IR and micro-Raman spectra of 2-(methylthio)nicotinic acid were recorded in the regions 400–4000 cm−1 and 100–4000 cm−1, respectively. In our calculations, the DFTB3LYP method with 6–311G(d, p) basis set was used to have the structural and spectroscopic data about the mentioned molecule in the ground state and the results obtained were compared with experimental values. Furthermore, gauge invariant atomic orbital (GIAO) 1H and 13C NMR chemical shifts in different solvents, UV-vis TD-DFT calculations, the highest occupied molecular orbitals (HOMO-2, HOMO-1, HOMO), lowest unoccupied molecular orbital (LUMO), molecular electrostatic potantial (MEP) surface, atomic charges and thermodynamic properties of molecule have been theoretically verified and simulated at the mentioned level. The energetic behavior of title molecule in different solvent media was investigated by using DFT/B3LYP method with 6–311G(d, p) basis set in terms of integral equation formalism polarizable continuum model (IEFPCM). In addition, the calculated infrared intensities, Raman activities, reduce masses and force constants of the compound under study have been also reported.
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D. Miklos, P. Segl’a, M. Palicova, M. Kopcova, M. Melnik, M. Valko, T. Glowiak, M. Korabik, and J. Mrozinski, Polyhedron 20, 1867 (2001).
P. Segl’a, J. Miklovic, D. Miklos, V. Mrazova, L. Krupkova, D. Hudecova, Z. Ondrusova, J. Svorec, J. Moncol, and M. Melnik, Transition Met. Chem. 34, 15 (2009).
S. Gao, J. Liu, J. Huo, Z. Sun, J. Gao, and S. Weng Ng, Acta Cryst. C 60, m363 (2004).
M. Karabacak, M. Čınar, and M. Kurt, J. Mol. Struct. 885, 28 (2008).
P. Koczon, T. Hrynaszkiewicz, R. Swislocka, M. Samsonowicz, and W. Lewandowski, Vibrational Spectrosc. 33, 215 (2003).
R. Swislocka, E. Regulska, M. Samsonowicz, and W. Lewandowski, Polyhedron 28, 2556 (2009).
N. K. Singh and D. K. Singh, Synth. React. Inorg. Met.-Org. Chem. 32, 203 (2002).
P. Segl’a, J. Miklovic, D. Miklos, J. Titis, R. Herchel, J. Moncol, B Kalinakova, D. Hudecova, V. Mrazova, T. Lis, and M. Melnik, Transition Met. Chem. 33, 967 (2008).
B. Dudova, D. Hudecova, R. Pokorny, M. Mikulasova, M. Palicova, P. Segl’a, and M. Melnik, Folia Microbiol. 46, 379 (2001).
S. Basavoju, C. M. Reddy, and G. R. Desiraju, Acta Cryst. E 61, 822 (2005).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, i J.V.Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03. Revision D. 01 (Gaussian Inc. Wallingford, 2004).
A. Frisch, A. B. Nielson, and A. J. Holder, GAUSS-VIEW User Manual (Gaussian Inc. Wallingford, 2003).
A. D. Becke, J. Chem. Phys. 98, 5648 (1993).
C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37, 785 (1988).
J. B. Foresman and E. Frisch, Exploring Chemistry with Electronic Structure Methods (Gaussian Inc. Pittsburgh, 1993).
J. P. Merrick, D. Moran, and L. Radom, J. Phys. Chem. A 111, 11683 (2007).
M. H. Jamr’oz, Vibrational Energy Distribition Analysis (VEDA4, Warsaw, 2004).
R. Ditchfield, Mol. Phys. 27, 789 (1974).
F. London, J. Phys. Radium 8, 397 (1937).
K. Wolinski, J. F. Himton, and P. Pulay, J. Am. Chem. Soc. 112, 8251 (1990).
A. Vlcek, Jr. and S. Zalis, Coord. Chem. Rev. 251, 258 (2007).
B. H. Stuart, Infrared Spectroscopy: Fundamentals and Applications (Wiley, England, 2004).
R. M. Silverstein and F. X. Webster, Spectroscopic Identification of Organic Compounds (Wiley, New York, 1998).
G. Varsanyi, Vibrational Spectra of Benzene Derivatives (Academic, New York, 1969).
D. L. Pavia, G. M. Lampman, G. S. Kriz, and J. R. Vyvyan, Introduction to Spectroscopy (BROOKS/COLE CENGAGE, Learing, 2009).
L. J. Bellamy, The Infrared Spectra of Complex Molecules (Wiley, New York, 1975).
N. B. Colthup, L. H. Daly, and E. Wiberley, Introduction to Infrared and Raman Spectroscopy (Academic, New York, 1964).
L. G. Wade, Jr., Organic Chemistry (Prentice Hall, New Jersey, 2006).
M. K. Rofouei, E. Fereyduni, N. Sohrabi, M. Shamsipur, J. A. Gharamaleki, and N. Sundaraganesan, Spectrochim. Acta Part A 78, 88 (2011).
V. Krishnakumar, G. Keresztury, T. Sundius, and R. Ramasamy, J. Mol. Struct. 702, 9 (2004).
R. J. Anderson, D. J. Bendell, and P. W. Groundwater, Organic Spectroscopic Analysis (The Royal Society of Chemistry, Sanderland, UK, 2004).
K. Fukui, Science 218, 747 (1982).
A. Pirnau, V. Chi, O. Oniga, N. Leopold, L. Szabo, M. Baias, and O. Cozar, Vibrational Spectrosc. 48, 289 (2008).
J. S. Murray and K. Sen, Molecular Electrostatic Potentials Concepts and Applications (Elsevier, Amsterdam, 1996).
R. S. Mulliken, J. Chem. Phys. 23, 1833 (1982).
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Gökce, H., Bahçeli, S. Molecular structure, spectroscopic properties and DFT calculations of 2-(methylthio)nicotinic acid. Opt. Spectrosc. 115, 469–483 (2013). https://doi.org/10.1134/S0030400X13100044
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DOI: https://doi.org/10.1134/S0030400X13100044