Theoretical Study on Imidazopyridinyl-chalcones based Dimers Mechanism of Formation Using Quantum Chemistry Methods

Bibata KONATE¹, Sopi Thomas AFFI^1, , Doh Soro¹, Kafoumba BAMBA¹ and Nahossé ZIAO¹

¹Laboratoire de Thermodynamique et de Physico-Chimie du Milieu (LTPCM), Unité de Formation et de Recherche- Sciences Fondamentales et Appliquées (UFR-SFA), Université NANGUI ABROGOUA (UNA), Abidjan, Côte d’Ivoire

Cite this paper:
Bibata KONATE, Sopi Thomas AFFI, Doh Soro, Kafoumba BAMBA and Nahossé ZIAO. Theoretical Study on Imidazopyridinyl-chalcones based Dimers Mechanism of Formation Using Quantum Chemistry Methods. Journal of Materials Physics and Chemistry. 2022; 10(1):1-9. doi: 10.12691/jmpc-10-1-1

Abstract

Imidazo[1,2-a]pyridinyl-chalcones (IPCs) offer a broad spectrum of biological activities with molecular diversity possible by synthesis. Two potential reactive sites were identified within their basic molecular skeleton from which obtaining dimers by synthesis is possible. In this study, at the level B3LYP/6-311G(d), work focused on elucidating both the mode of bond formation between the two reactive sites and the concerted course of dimerization reaction in the IPC series according to the concepts and tools of transition state theory. Four substituted IPC molecules with stronger nematicidal activity were used in addition to the unsubstituted IPC molecule as monomers. Calculations performed on each initial reactive system modelled using two IPCs led to a unique transition structure in each case. Molecular dimerization in IPC series was found to follow a one-step reaction mechanism. It involved the formation of two covalent bonds, C₅–C₁₄׳, and C₁₄–C₂₉׳. The stabilization of the second bond was faster than the first which, moreover, required less energy for establishment. Analysis of bond lengths confirmed the stability of the bonds formed. The energy parameters and the characteristics of the reaction path proved the stability of the dimers envisaged with respect to the reagents used. The path of dimerization reaction in the IPC series was found to be substitution independent but the activation energies depended on the overall nucleophilicity of monomers.

Keywords:
Quantum chemistry Dimerization Imidazopyridinyl-chalcone Reaction mechanism DFT method

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References:

[1]	Kuthyala, S., Nagaraja, G.K., Sheik, S., Hanumanthappa, M. and Kumar, M.S. Synthesis of Imidazo[1, 2-a]pyridine-chalcones as Potent Inhibitors against A549 Cell Line and Their Crystal Studies, Journal of Molecular Structure 1177, 381-390, September 2018.
[2]	Rao, N.S., Kistareddy, C., Balram, B. and Ram, B. Synthesis and Antibacterial Activity of Novel Imidazo[1,2-a]pyrimidine and Imidazo[1,2-a]pyridine Chalcones Derivatives. Der Pharma Chemica 4, 2408-2415, January 2012.
[3]	Sissouma, D., Ouattara, M., Koné, M.W., Menan, H.E., Adjou, A. and Ouattara, L. Synthesis and in Vitro Nematicidal Activity of New Chalcones Vectorised by Imidazopyridine. Africa Journal of Pharmacy and Pharmacology, 5, 2086-2093. October, 2011.
[4]	Thomas, A.S., Nahossé, Z. and Kafoumba, B. Determination, par des méthodes ab initio et DFT, des sites et énergies de protonation d’une série de molécules d’imidazopyridinyl-chalcones substituées. European Scientific Journal,11, 148-158, November 2015.
[5]	Affi, T.S., Ziao, N., Ouattara, M., Sissouma, D. and Yapo, K) Caractérisation théorique des sites d’interaction par liaison hydrogène de 3-(4-isopropylphenyl)-1-(2-méthylimidazopyridin-3-yl)prop-2-en-1-one et de 3-(2-méthoxyphenyl)-1-(2-méthylimidazopyridin-3-yl)prop-2-en-1-one. European Journal of Scientific Research,123, 340-347, June 2014.
[6]	Gadkari, S., Choudhari, P., Bhatia, M., Khetmar, S. and Jadhav, S. 3D QSAR, Pharmacophore Identification Studies on Series of Imidazopyridine Analogs as Nematicidal Activity. Pharmacophore, 3, 199-208, 2012.
[7]	B. Meunier, “Les molécules hybrides comme stratégie de création de nouveaux agents anti-infectieux,” Comptes Rendus Chim., vol. 14, no. 4, pp. 400-405, March 2011.
[8]	B. Konate, S. T. Affi, and N. Ziao, “DFT Study of Dimerization Sites in Imidazo [1, 2-a] pyridinyl-chalcone Series,” pp. 1-17, December 2020.
[9]	Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J. and Fox, D. J. (2009). Gaussian 09
[10]	H. Eyring, “The Activated Complex in Chemical Reactions,” J. Chem. Phys., vol. 3, no. 2, pp. 107-115, November 1934.
[11]	S. H. B. Chunyang P., “Combining ST and QN Methods to Find Transition States,” Isr. J. Chem., vol. 33, pp. 449-454, July 1993.
[12]	C. Peng, P. Y. Ayala, H. B. Schlegel, and M. J. Frisch, “to Optimize Equilibrium Geometries and Transition States,” J. Comput. Chem., vol. 17, no. 1, pp. 49-56, January 1996.
[13]	V. Barone, M. Cossi, and J. Tomasi, “A new definition of cavities for the computation of solvation free energies by the polarizable continuum model,” J. Chem. Phys., vol. 107, no. 8, pp. 3210-3221, May 1997.
[14]	E. Cancès, B. Mennucci, and J. Tomasi, “A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to Isotropic and anisotropic dielectrics,” J. Chem. Phys., vol. 107, no. 8, pp. 3032-3041, May 1997.
[15]	M. Cossi, V. Barone, R. Cammi, and J. Tomasi, “Ab initio study of solvated molecules: A new implementation of the polarizable continuum model,” Chem. Phys. Lett., vol. 255, no. 4-6, pp. 327-335, Fabruary 1996.
[16]	M. Cossi, G. Scalmani, N. Rega, and V. Barone, “New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution,” J. Chem. Phys., vol. 117, no. 1, pp. 43-54, April 2002.
[17]	J. Tomasi and M. Persico, “Molecular Interactions in Solution : An Overview of Methods Based on Continuous Distributions of the Solvent An Overview of Different Approaches to,” pp. 2027-2094, August 1994.