Abstract
By using the combination of density functional theory (DFT) B3LYP/6-311++G(d,g) within polarized continuum (PCM) model, solvent effects on 3-hydroxy-2-quinoxalinecarboxylic acid (3HQC) tautomers were investigated. Geometrical parameters, vibrational frequencies, electronic and energetic properties, and the nucleus-independent chemical shifts (NICS) were calculated in benzene, diethyl ether, and water. It has been seen that these molecular features of 3HQC are mostly solvent dependent.
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W. Yan, Y. Xue, H. Zhu, J. Zeng, and D. Xie, J. Comput. Chem. 25, 1833001839 (2004).
L. Onsager, J. Am. Chem. Soc. 58, 1486 (1936).
L. Rivail and D. Rinaldi, Theor. Chim. Acta 32, 57 (1973).
S. Miertuš, E. Scrocco, and J. Tomasi, Chem. Phys. 55, 117 (1981).
R. J. Hall, M. M. Davidson, N. A. Burton, and I. H. Hillier, J. Phys. Chem. 99, 921 (1995).
S. Badoǧlu and Ş. Yurdakul, Spectrochim. Acta A 101, 14 (2013).
U. Erez, H. Frenk, O. Goldberg, A. Cohen, and V. I. Teichberg, Eur. J. Pharm. 110, 31 (1985).
P. Frey, D. Bemey, P. L. Herrling, W. Mueller, and S. Urwyler, Neurosci. Lett. 91, 194 (1988).
K. Hatta, Y. Yamamoto, Y. Hori, M. Okuwa, and T. Moroji, Neurosci. Lett. 138, 53 (1992).
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, V. Bakken, 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, 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 09 Revision C. 01 (2009).
M. H. Jamróz, Vibrational Energy Distribution Analysis VEDA 4 (2004).
H. Watanabe, N. Hayazawa, Y. Inouye, and S. Kawata, J. Phys. Chem. B 109, 5012 (2005).
M. A. Palafox, G. Tardajos, A. Guerrero-Martinez, V. K. Rastogi, D. Mishra, S. P. Ojha, and W. Kiefer, Chem. Phys. 340, 17 (2007).
K. Fukui, Science 218, 747 (1987).
P. V. R. Schleyer and H. Jiao, Pure Appl. Chem. 68, 209 (1996).
T. M. Krygowski, M. Cyrański, A. Ciesielski, B. Swirska, and P. Leszczyński, J. Chem. Inf. Comput. Sci. 36, 1135 (1996).
P. V. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, and N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 118, 6317 (1996).
S. Badoǧlu and Ş. Yurdakul, Struct. Chem. 21, 1103 (2010).
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Badoǧlu, S., Yurdakul, Ş. DFT study of solvent effects on 3-hydroxy-2-quinoxalinecarboxylic acid tautomers. Opt. Spectrosc. 117, 201–212 (2014). https://doi.org/10.1134/S0030400X14080049
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DOI: https://doi.org/10.1134/S0030400X14080049