A Computational Study on Structural and Electronic Properties of 1-(4-Chlorophenyl)-2-{[5-(4-Chlorophenyl)-1,2,3-Oxadiazol-2-Yl]Sulfanyl}Ethanone

Abstract:

In this paper, a first principle Density Functional Theory (DFT) method was conducted to study the geometric and electronic structures of 1-(4-chlorophenyl)-2-{[5-(4-chlorophenyl) -1,3,4-oxadiazol-2-yl] sulfanyl} ethanone, C₁₆H₁₀C_l2N₂O₂S. Using B3LYP level of theory with four basis sets of 6-31G**, 6-31++G**, 6-311G**, and 6-311++G**, the equilibrium structure of the title molecule was used to determine the total energies, Frontier molecular orbital’s energies, Mulliken atomic charges, and others. The computed findings present that four total energies obtained are close to each other, with the corresponding values of-59716.06 eV, -59709.42 eV, -59708.56 eV, and-59716.51 eV, respectively for B3LYP/6-31G**, B3LYP/6-31++G**, B3LYP/6-311G**, and B3LYP/6-311++G** methods. The calculated HOMO-LUMO energy gaps were predicted in the range of 4.001 eV - 4.089 eV. In this study, the atomic charge values of molecular system were also determined using Mulliken Population Analysis (MPA) approach. For DFT/B3LYP/6-311G** level of calculation, the computed results show that the atom of C₈ accommodates the highest negative charge in the title molecular system. All the oxygen, nitrogen, and chloride atoms are having negative charges, whereas all the hydrogen atoms are having positive charges. In addition, the dipole moment value was also determined to be 1.4758 Debye by employing DFT/B3LYP/6-311G** level of theory.

• Periodical: Applied Mechanics and Materials (Volume 892)
• Pages: 1-7
• DOI: https://doi.org/10.4028/www.scientific.net/AMM.892.1
• Online since: June 2019
• Authors: Pek Lan Toh*, Montha Meepripruk, Rosfayanti Rasmidi
• Keywords: 1-(4-Chlorophenyl)-2-{[5-(4-Chlorophenyl)-1,3,4-Oxadiazol- 2-Yl]Sulfanyl}Ethanone, Density Functional Theory, Electronic Structures, Geometrical Parameters

References

[1] A. Husain, M. Ajmal, Synthesis of novel 1,3,4-oxadiazole derivatives and their biological properties, Acta Pharm. 59 (2009) 223-233.

[2] S. Kumar, Synthesis of some 2-amino-5-substituted-1,3,4-oxadiazole derivatives in the acetic acid, E-J. Chem. 8 (2011) S448-S454.

DOI: 10.1155/2011/757381

[3] M. Malhotra, M. Sanduja, A. Samad and A. Deep, A. New oxadiazole derivatives of isonicotinohydrazide in the search for antimicrobial agents: Synthesis and in vitro evaluation, J. Serb. Chem. Soc. 77(1) (2012) 9-16.

DOI: 10.2298/jsc110123155m

[4] S. Bala, S. Kamboj, V. Saini, and D. N. Prasad, 1,3,4-Oxadiazole Derivatives: Synthesis, Characterization, Antimicrobial Potential, and Computational Studies, BioMed Research International 2014 (2014) 172791-1-18.

DOI: 10.1155/2014/172791

[5] K. V. Vani, G. Ramesh, C. V. Rao, Synthesis of new triazole and oxadiazole derivatives of quinazolin-4(3H)-one and their antimicrobial activity, J. Heterocyclic Chem. 53 (2016) 719-726.

DOI: 10.1002/jhet.2353

[6] Y. Luo, Z. J. Liu, G. Chen, J. Shi, J. R. Li, H. L. Zhu, 1,3,4-. Oxadiazole derivatives as potential antitumor agents: Discovery, optimization and biological activity valuation. MedChemComm 7(2) (2016) 263-271.

DOI: 10.1039/c5md00371g

[7] R. Kumar, S. Hussain, K. M. Khan, S. Perveen, S. Yousuf, Crystal structure and Hirshfeld surface analysis of 1-(4-chloro­phen­yl)-2-{[5-(4-chloro­phen­yl)-1,3,4-oxa­diazol-2-yl]sulfan­yl}ethanone, ActaCryst. E. 73 (2017) 524-527.

[8] M. Soleiman-Beigi, R. Aryan, M. Yousofizadeh, and Sh. Khosravi, A combined synthetic and DFT study on the catalyst-free and solvent-assisted synthesis of 1,3,4-oxadiazole-2-thiol derivatives, J. Chem. (2013) 476358-1-6.

DOI: 10.1155/2013/476358

[9] H. Wang, F. Q. Bai, X. Jia, D. Cao, R. M. Kumar, J. L. Brédas, S. Qu, B. Bai, H. X. Zhang and M. Li, Theoretical study on molecular packing and electronic structure of bi-1,3,4-oxadiazole derivatives, RSC Adv. 4 (2014) 51942-51949.

DOI: 10.1039/c4ra06405d

[10] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian 09, Revision E.01, Gaussian, Inc., Wallingford CT, (2016).