Abstract
Density functional theory (DFT) method at the level of B3LYP with 6–311G(d) basis set was used to investigate the effects of a variety of substituents (H, NH2, NMe2, OCH3, CH3, Cl, Br, CN, NO2) on the electronic and structural properties of 2,4-diamino-5-p-substituted-phenyl-6-ethyl-pyrimidines. The investigation showed that the atomization energy was affected by substitution. Likewise, the molecular orbitals HOMO and LUMO and energy gap ΔE were affected by the substituent. Dipole moment was also affected by the introduction of the substituent. On the other hand, the Mulliken charges at only C1′, C2 and N7, were correlated with both MSP and DSP models.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B.A. Saleh, J. Mol. Struct. THEOCHEM 915 (2009) 47.
J. Shorte, Correlation Analysis of Organic Reactivity, Chaps. 3 and 4, Research Studies Press, Wiley, Chichester, 1982.
L.P. Hammett, Physical Organic Chemistry, 2nd ed., Chap. 11, McGraw-Hill, New York, 1970.
J. Shorter, Prog. Phys. Org. Chem. 17 (1990) 1.
J. Shorter, Chem. Intelligencer 2 (1996) 39.
O. Exner, Correlation Analysis of Chemical Data, Plenum, New York and SNTL, Prague, 1988.
O. Exner, in: N.B. Chapman, J. Shorter (Eds.), Correlation Analysis in Chemistry, Recent Advances Plenum, New York, 1978.
B.A. Saleh, A.H. Essa, S.A.O. Al-Shawi, A.F. Jalbout, J. Mol. Struct. THEOCHEM 909 (2009) 107.
B.A. Saleha, S.A. Al-Shawia, G.F. Fadhil, J. Phys. Org. Chem. 21 (2008) 96.
A.H. Essa, B.A. Saleh, A.J. Hameed, J. Comput. Theoret. Nanosci. 6 (2009) 706.
V. Wiwanitkit, Malaria Research in Southeast Asia, Nova Science Publishers, Inc., 2007, p. 47.
National Center for Infectious Diseases, Division of Parasitic Diseases (2007) Internet references. Retrieved from http://www.cdc.gov/malaria/facts.htm
E.B. Burgina, V.P. Baltakhinov, E.V. Boldyreva, T.P. Shakhtschneider, J. Struct. Chem. 45 (2004) 64.
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, J.A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, 2004.
R. Krishnan, J.S. Kinkley, R. Seeger, J.A. Pople, J. Chem. Phys. 72 (1980) 650.
C. Hansch, A. Leo, R.W. Taft, Chem. Rev. 91 (1991) 165.
S. Ehrensons, R.T.C. Brownlee, R.W. Taft, Prog. Phys. Org. Chem. 10 (1973) 1.
K. Tuppurainen, S. Lötjönen, R. Laatikainen, T. Vartiainen, U. Maran, M. Strandberg, T. Tamm, Mutat. Res. 247 (1991) 97.
D.F.V. Lewis, C. Ioannides, D.V. Parke, Xenobiotica 24 (1994) 401.
M. Karelson, V.S. Lobanov, A.R. Katritzky, Chem. Rev. 96 (1996) 1027.
G.K. Hamer, I.R. Peat, W.F. Reynolds, Can. J. Chem. 51 (1973) 897
G.K. Hamer, I.R. Peat, W.F. Reynolds, Can. J. Chem. 51 (1973) 915.
J. Bromilow, R.T.C. Brownlee, D.J. Craik, P.R. Fiske, J.E. Rowe, M. Sadek, J. Chem. Soc., Perkin Trans. 2 (1981) 753
R.T.C. Brownlee, D.J. Craik, J. Chem. Soc., Perkin Trans. 2 (1981) 760
R.T.C. Brownlee, D.J. Craik, J. Org. Magn. Reson. 15 (1981) 248.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Saleh, B.A., Abood, H.A., Miyamoto, R. et al. Theoretical study of substituent effects on electronic and structural properties of 2,4-diamino-5-para-substituted-phenyl-6-ethyl-pyrimidines. JICS 8, 653–661 (2011). https://doi.org/10.1007/BF03245897
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF03245897