Theoretical study of the Solvent effects on Electronic properties of 2(1H)-quinoxalinone derivatives
Abstract
The structures and electronic spectra of three quinoxalinone derivatives have been investigated theoretically by performing DFT and TDDFT calculations with standard basis sets containing polarization and diffuse functions. The solvent effect was taken into account using self-consistent isodensity polarized continuum model (SCIPCM); three polar solvents were considered. The effect of the solvent polarity on the geometries, solvation energies, dipole moment, energy gap between HOMO and LUMO and UV-visible electronic transitions were examined for all studied compounds. The theoretical electronic spectrum of 2(1H)-quinoxalinone was compared with the experimental one. The experimental electronic spectrum recorded in ethanol exhibit three absorption bands respectively at 230, 280 and 220 nm. The existence of these bands has been confirmed by TDDFT calculations for the studied quinoxalinone derivatives. The effects of solvent polarity and the nature of the substituent of the quinoxalinone on the displacement of the calculated absorption bands are discussed.References
V. Krishnakumar, N. Prabavathi, Spectrochim. Acta Part A, 2010, 77, 238–247.
H. Kinashi, S.L. Otten, J.S. Duncan, C.R. Hutchinson, J. Antibiot. 41 (1988) 624–637.
R. Sarges, H.R. Howard, R.G. Browne, L.A. Lebel, P.A. Seymour, B.K. Koe, J. Med.
Chem. 33 (1990) 2240–2254.
W. Losher, H. Lehmann, B. Behl, W. Lubish, T. Hoger, H.G. Lemair, G. Gross, Eur.
J. Neurosci. 11 (1999) 250–262.
P. Sanna, A. Carta, M. Loriga, S. Zanetti, L. Sechi, II Farmaco 53 (1998) 455-461.
Y.B. Kim, Y.H. Kim, J.Y. Park, S.K. Kim, Bioorg. Med. Chem. Lett. 14 (2004) 541-544.
S.T. Hazeldine, L. Polin, J. Kushner, K. White, T.H. Corbett, J. Biehl, J.P. Horwitz,
Bioorg. Med. Chem. 13 (2005) 1069-1081
S.T. Hazeldine, L. Polin, J. Kushner, K. White, T.H. Corbett, J. Biehl, J.P. Horwitz,
Bioorg. Med. Chem. 13 (2005) 3910-3920.
S.T. Hazeldine, L. Polin, J. Kushner, K. White, N.M. Bouregeois, B. Crantz, E. Palomino, T.H. Corbett, J. Biehl, J.P. Horwitz, Bioorg. Med. Chem. 45 (2002) 3130-3137.
S.T. Hazeldine, L. Polin, J. Kushner, J. Paluch, K. White, M. Edelstein, E. Palomino, T.H. Corbett, J.P. Horwitz, Bioorg. Med. Chem. 44 (2001) 1758-1776.
Y. Ikeda, E. Kuwano, M. Eto, J. Fac. Agric. 37 (1992) 81–92.
Y. Ura, G. Sakata, K. Makino, T. Ikai, Y. Kawamura, German Offenlegungschrift DE, 3004770.
N.T. Ghomsi, N.H. Ahabchane, N. Es-Safi, B. Garrigues, E.M. Essasi, Spectrosc. Lett. 40 (2007) 741–751.
D. Rose, E. Liesk, H. Hoeffkes, K.-G. A. Hengel, German Offenlegungschrift DE, 3 (1999) 212.
K. Toshima, R. Takano, T. Ozawa, S. Matsumura, J. Chem. Soc. Chem. Commun.(2002) 212.
G. Ughetto, A.H.J. Wang, G.J. Quigley, G.A. Van Der Marel, J.H. Van Boom, A. Rich, Nucleic Acids Res. 13 (1985) 2305-2323.
M.A. Viswamitra, O. Kennard, W.B.T. Cruse, E. Egert, G.M. Sheldrick, P.G. Jones, M.J. Waring, L.P.G. Wakelin, R.K. Olsen, Nature (London) 289 (1981) 817.
M.A. Palafox, G. Tardajos, A.G. Martines, V.K. Rastogi, D. Mishra, S.P. Ojha, W. Kiefer, Chem. Phys. 340 (2007) 17-31.
N.C. Handy, P.E. Masley, R.D. Amos, J.S. Andrews, C.W. Murray, G. Laming, Chem. Phys. Lett. 197 (1992) 506-515.
N.C. Handy, C.W. Murray, R.D. Amos, J. Phys. Chem. 97 (1993) 4392-4396.
P.J. Stephens, F.J. Devlin, C.F. Chavalowski, M.J. Frisch, J. Phys. Chem. 98 (1994) 11623-11627.
F.J. Devlin, J.W. Finley, P.J. Stephens, M.J. Frisch, J. Phys. Chem. 99 (1995) 16883-16902.
J.-P. Cornard, C. Lapouge, Chem. Phys. Lett. 438 (2007) 41-47.
J.-P. Cornard, C. Lapouge, J.-C. Merlin, Chem. Phys. 340 (2007) 273-282.
Ş. Yurdakul, T. Polat , Journal of Molecular Structure 963 (2010) 194–201
N. Padjama, S. Ramakumar, M.A. Viswamitra, Acta Cryst. C 43 (1987) 2239-2240.
N. Prabavathi, A. Nilufer, V. Krishnakumar, Spectrochimica Acta Part A 92 (2012) 325– 335.
S.M. Soliman, J. Albering, M.A.M. Abu-Youssef, Journal of Molecular Structure 1053 (2013) 48–60.
S. Badoğlu, Ş. Yurdakul, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 101 (2013) 14–21.
Y.S. Hong, H.M. Kim, Y.T. Park, H.S. Kim, Bull. Korean Chem. Soc. 21 (2000) 133-136.
A.D. Becke, J. Chem. Phys. 96 (1992) 9489–9495.
A.D. Becke, J. Chem. Phys. 98 (1993) 1372–1377.
C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785–789.
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, 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, J.A. Pople, Gaussian 03, Revision B.01, Gaussian, Inc., Pittsburgh, PA, 2003.
J.B. Foresman, T.A. Keith, K.B. Wiberg, J. Snoonian, M.J. Frisch, J. Phys. Chem. 100 (1996) 16098-16104.
G.A. Jaffrey, an Introduction to Hydrogen Bonding, Oxford University Press, (1997) 32.
S. Sudha, N. Sundaraganesan, K. Vanchinathan, K. Muthu, SP. Meenakshisundaram, Journal of Molecular Structure 1030 (2012) 191–203.
R.M. Issa, M.K. Awad, F.M. Atlam, Appl. Surf. Sci. 255 (2008) 2433–2441.
D. Jacquemin, J. Preat, E.A. Perpete, Chem. Phys. Lett. 410 (2005) 254-259.
D. Jacquemin, J. Preat, M. Charlot, V. Wathelet, J.M. Andre, E.A. Perpete, J. Chem. Phys. 121 (2004) 1736-1743.
M. Cossi, V. Barone, J. Chem. Phys. 115 (2001) 4708-4717.
N. Prabavathi, A. Nilufer, V. Krishnakumar, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 121 (2014) 483–493.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).
