Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Theoretical Investigation of 5-(4-Dimethylaminobenzylidene)thiobarbituric Acid
Corresponding Author(s) : Karrar A.S. Al-Ameed
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
In this study, synthesis of 5-benzylidene thiobarbituric acid derivative has been described. The route of preparation involved the uses of thiobarbituric acid as starting material and treated with 4-dimethylaminobenzaldehyde compound to give required derivative. This compound was identified by spectroscopic methods; H NMR, FTIR and CHNS analysis and also by measuring its melting point. A theoretical investigation is performed using hybrid Beck model (B3LYP), ESP showed regular distribution of charge density of whole molecule when one of the two proton is removed from a-carbon, the ESP for HOMO electron density is heavily localized on a negative carbon, reflect the reactivity of thiobarbituric molecule and show it as highly effective nucleophile when act into nucleophilic substitution reactions.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- N. Tavakoli-Hoseini, M.M. Heravi and F.F. Bamoharram, Asian J. Chem., 22, 7208 (2010).
- A.I.D. Yachkov, B.A. Ivin, N.A. Smorygo and E.G. Sochilin, Zh. Org. Khim., 12, 1115 (1976).
- B.Q. Yang, J. Lu and M. Tian, Chinese Chem. Lett., 14, 1240 (2003).
- M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian,A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr. J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, 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, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian, Inc., Wallingford CT (2009).
- A.D. Becke, J. Chem. Phys., 98, 1372 (1993).
- N.T. Fan, Examples of Organic Synthesis, Beijing University of Science and Technology Press, Beijing,, p. 215 (1995).
References
N. Tavakoli-Hoseini, M.M. Heravi and F.F. Bamoharram, Asian J. Chem., 22, 7208 (2010).
A.I.D. Yachkov, B.A. Ivin, N.A. Smorygo and E.G. Sochilin, Zh. Org. Khim., 12, 1115 (1976).
B.Q. Yang, J. Lu and M. Tian, Chinese Chem. Lett., 14, 1240 (2003).
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian,A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr. J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, 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, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian, Inc., Wallingford CT (2009).
A.D. Becke, J. Chem. Phys., 98, 1372 (1993).
N.T. Fan, Examples of Organic Synthesis, Beijing University of Science and Technology Press, Beijing,, p. 215 (1995).