Theoretical Studies on the Isomers of Quinazolinone by first Principles
Author Affiliations
- 1Physics Department, University of Lucknow, Lucknow, INDIA
Res. J. Recent Sci., Volume 1, Issue (3), Pages 11-18, March,2 (2012)
Abstract
The present communication is aimed at comparing the molecular structural properties, vibrational and energetic data of 2- and 4- quinazolinone, the two isomers of Quinazolinone, a biologically active hetrocyclic compound, in gas phase, due to their pharmacological activities and applications. The ground state properties of the two isomers have been calculated employing DFT/ B3LYP level of theory using the basis sets 6-311G(d), 6-311+G(d,p), 6-311++G(d,p). The dipole moment and mean polarizability are calculated to be 6.4687 Debye and 110.202/a.u. in case of 2- quinazolinone and for 4-quinazolinone these values are 1.4611 Debye and 107.663/a.u. at B3LYP/ 6-311++G(d,p) level of theory. MESP surfaces have also been drawn and compared. In order to obtain a complete description of molecular dynamics, vibrational wavenumber calculation along with the normal mode analysis, have been carried out at the DFT level.
References
- Prasad K.S., Kumar L.S., Chandan S., Jayalakshmi B., Revanasiddappa H.D., Diorganotin(IV) complexes of biologically potent 4(3H)-quinazolinone derived Schiff bases: synthesis, spectroscopic characterization, DNA interaction studies and antimicrobial activity, Spectrochim Acta A Mol Biomol Spectrosc., 81(1), 276-82 (2011)
- Kohli D., Hashim S.R., Vishal S., Sharma M. and Singh A.K., Synthsis and antibacterial activity of quinazolinone derivatives, International Journal of Pharmacy and Pharmaceutical Sciences, 1(1) , (2009)
- Singh T., Sharma S., Srivastava V.K. and Kumar A., Synthesis, insecticidal and antimicrobial activities of some heterocyclic derivatives of Quinazolinone, Indian Journal of chemistry, 45 (B) 2558-2565 (2006)
- Alagarsamy V., Muthukumar V., Pavalarani N., Vasanthanathan P., and Revathi R. , Synthesis, Analgesic and Anti- inflammatory Activities of Some Novel 2,3- Disubstituted Quinazolinone-4 (3H)-one, Biol. Pharm. Bull., 26(4) 557-559 (2003)
- Ouyang G., Zhang P., Xu G., Song B., Yang S., Jin L., Xue Wu, Hu D., Lu P. and Chen. Z. Synthesis and Antifungal Bioactivities of 3-Alkylquinazolin-4-one Derivatives, Molecules,(11) 383-392 (2006)
- Nanda A.K., Ganguli S. and Chakraborty R., Antibacterial Activity of Some 3-(Arylideneamino)-2-phenylquinazoline-4(3H)-one: Synthesis and Preliminary QSAR Studies, Molecules,(12) 2413-2426 (2007)
- Chandrika P.M., Yakaiah T., Rao A.R.R., Narsaiah B., ChakraReddy N., Sridhar V., Rao J.V., Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity (cytotoxic) against U937 leukemia cell lines, European Journal of Medicinal Chemistry, 147-152 (2007)
- Priya M.G.R., Girijaand K., Ravichandran N. Invitro Study of Anti -inflammatory and Antioxidant Activity of 4-(3H)-Quinazolinone Derivatives, Centre for Advanced Research in Indian System of Medicine, 4(2), 418-424 (2011)
- Alagarsamy V., Giridhar R., Yadav M.R., Revathi R., Ruckmani K., Clercq E.D., AntiHIV, antibacterial and antifungal activities of some novel 1,4-disubstituted-1,2,4-triazolo[4,3-a] quinazolin-5(4 h )-ones Indian Journal of Pharm. Sci., Year, 68(4), 532-535 (2006)
- Jing X., Zhen Li, Xin Pan and Yao-Cheng Shi, A Novel Method for the Synthesis of 4(3)-Quinazolinones, Journal of the Chinese Chemical Society, (55), 1145-1149 (2008)
- Kohn W., Sham L.J., Self-consistent equations including exchange and correlation effects, Phys. Rev., (140)1133–1138 (1965)
- Becke A.D., Density functional thermochemistry. III. The role of exact exchange, J. Chem. Phys.,(98) 648– 5652 (1993)
- Lee C.,Yang W. , Parr R.G., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. (37) 785–789 (1998)
- Miehlich B., Savin A., Stoll A., Preuss H., Results obtained with the correlation energy density functional of Becke and Lee,Yang and Parr,Chem. Phys. Lett.(157)200–206 (1989)
- Frisch M.J. et. al. Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford CT, ( 2009)
- Scott A.P. and Random L., Harmonic vibrational frequencies: An evaluation of Hartree–Fock, Møller–Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors, J. Phys. Chem.-US, (100), 16502-16513 (1996)
- Denington II, Roy, Keith T., Millam J., Eppinnett K. Hovell W.L. and Gilliland, R., Gauss View, Version 3.07 Semichem, Inc., Shawnee Mission, KS, (2003)
- Jamroz M.H., Vibrational Energy Distribution Analysis: VEDA 4 program, Warsaw (2004)
- Ladd M., Introduction to Physical Chemistry, third ed., Cambridge University Press, Cambridge, (1998)
- Fleming I., Frontier Orbitals and Organic Chemical Reactions, John Wiley and Sons, New York, 5-27 (1976)
- Ggadre S.R. and Pathak R.K., Miximal and minimal characteristics of molecular electrostatic potentials, J. Chem. Phys. ( 93) 1770–1774 (1990)
- Ggadre S.R. and Shrivastava I.H., Shapes and sizes of molecular anions via topographical analysis of electrostatic potential, J. Chem. Phys. (94) 4384–4390 (1991)
- Murray J.S. and Sen K., Molecular Electrostatic Potentials, Concepts and Applications, Elsevier, Amsterdam, (1996)
- Alkorta I. and Perez J.J. , Molecular polarization potential maps of the nucleic acid bases, Int. J. Quant. Chem., (57) 123–135 (1996)
- Scrocco E. and Tomasi J., Advances in Quantum Chemistry, ( 2),P. Lowdin, ed., Academic Press, New York (1978)
- Luque F.J., Orozco M., Bhadane P.K., and Gadre S.R., SCRF calculation of the effect of water on the topology of the molecular electrostatic potential, J. Phys. Chem., ( 97) 9380–9384 (1993)
- Prasad O., Sinha L., and Kumar N.,Theoretical Raman and IR spectra of tegafur and comparison of molecular electrostatic potential surfaces, polarizability and hyerpolarizability of tegafur with 5-fluoro-uracil by density functional theory, J. At. Mol. Sci.,(1) 201-214(2010)