3-Metil-4-(4-karboksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on Üzerine Bazı Teorik Hesaplamalar

Hilal Medetalibeyoğlu; Onur Akyıldırım; Haydar Yüksek

Research Article

Some Theoretical Calculations on 3-Methyl-4-(4-carboxybenzylidenamino)- 4,5-dihydro-1H-1,2,4-triazol-5-one

Year 2019, Volume: 6 Issue: 1, 13 - 27, 30.06.2019

Hilal Medetalibeyoğlu , Onur Akyıldırım , Haydar Yüksek

Abstract

In this paper, the optimization of 3-methyl-4-(4-carboxybenzylidenamino)-4,5-dihydro-1H-1,2,4- triazol-5-one was performed by using DFT (B3LYP/B3PW91) and 6-31++G(d,p) basis set. Starting with optimized structure, 1H-NMR chemical shift values of the compound were calculated in DMSO and CCl4 solvents media by using GIAO and CSGT methods. UV-vis and IR frequency values of the molecule were calculated and the relationship between experimental and theoretical results were evaluated. Also, the bond angles, dihedral angles, bond lengths, electronic properties, mulliken atomic charges, HOMO-LUMO energies and MEP maps of the molecule were measured by using the same basis set and method.

Keywords

1H-1.2.4-triazol-5-on, Gaussian09W, 6-31++G(d, p), GIAO, CSGT, B3LYP

References

Adam, MSS, Elsawy, H, (2018). “Biological potential of oxo-vanadium salicylediene amino-acid complexes as cytotoxic, antimicrobial, antioxidant and DNA interaction”, J. Photochem. Photobiol., B 184, 34-43.
Akyıldırım, O, (2005). “3-Alkil(Aril)-4-(4-karboksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin Sentezi, Yapılarının Aydınlatılması ve Susuz Ortam Titrasyonları”, Yüksek Lisans Tezi, Kafkas Üniversitesi, Fen Bilimleri Enstitüsü.
Becke, AD, (1988). “Density-functional exchange-energy approximation with correctasymptotic behavior”, Phys. Rev. A: General physics, 38(6), 3098-3100.
Becke, AD, (1993). “Density‐functional thermochemistry. III. The role of exact Exchange”, J. Chem. Phys, 98, 372-377.
Chandramouli, C, Shivanand, M, Nayanbhai, T, Bheemachari, B, Udupi, R, (2012).“Synthesis and biological screening of certain new triazole Schiff bases and their derivatives bearing substituted benzothiazole moiety”, J. Chem. Pharmaceut. Res. 4 (2), 1151-1159.
Cramer, CJ, (2004). Essentials of Computational Chemistry: Theories and Models Computational Chemistry, 596.
Dehkhodaei, M, Sahihi, M, Rudbari, HA, Ariaeefar, M, Gharaghani, S, Azadbakht, R, Taheri, S, Abbasi Kajani, A, (2018). “Multi experimental and computational studies for DNA and HSA interaction of new nano-scale ultrasoundassisted synthesized Pd(II) complex as a potent anticancer drug”, J. Mol. Liq. 264, 386-397.
Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, Scalmani, G, Barone, V, Mennucci, B, Petersson, GA, Nakatsuji, H, Caricato, M, Li, X, Hratchian, HP, Izmaylov, AF, Bloino, J, Zheng, G, Sonnenberg, JL, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Vreven, T, Montgomery, JA, Vreven, TJr, Peralta, JE, Ogliaro, F, Bearpark, M, Heyd, JJ, Brothers, E, Kudin, N, Staroverov, VN, Kobayashi, R, Normand, J, Raghavachari, K, Rendell, A, Burant, JC, Iyengar, SS, Tomasi, J, Cossi, M, Rega, N, Millam, JM, Klene, M, Knox, JE, Cross, JB, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, RE, Yazyev, O, Austin, AJ, Cammi, R, Pomelli, CJ, Ochterski, W, Martin, LR, Morokuma, K, Zakrzewski, VG, Voth, GA, Salvador, P, Dannenberg, JJ, Dapprich, S, Daniels, AD, Farkas, O., Foresman, J. B., Ortiz, J. V, Cioslowski, J, and Fox, DJ, 2009. Gaussian Inc. (Wallingford, CT).
Gans P, (1971). Vibrating Molecules. Chapman and Hall, 18-59.
Jamroz, MH, (2004). Vibrational Energy Distribution Analysis VEDA4 (Warsaw).
Keith, T, Millam, J, (2009). GaussView, Version 5, R Dennington, Semichem Inc, Shawnee Mission, KS.
Kumar, G, Devi, S, Kumar, D, (2016). “Synthesis of Schiff base 24-membered trivalent transition metal derivatives with their anti-inflammation and antimicrobial evaluation”, J. Mol. Struct. 1108, 680-688.
Lee, C, Yang, W, Parr, RG, (1988). “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”, Phys. Rev. B , 37, 785-789.
Levine, IN. (2000). Many‐Electron Atoms. Quantum chemistry. Prentice‐ Hall Inc, 739s. New Jersey.
Luszczki, JJ, Plech, T, Wujec, M, (2012). “Effect of 4-(4-bromophenyl)-5-(3- chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione on the anticonvulsant action of different classical antiepileptic drugs in the mouse maximal electroshock-induced seizure model”, Eur. J. Pharmacol. 690, 99-106.
Mulliken RS, (1955). “Electronic Population Analysis on LCAO–MO Molecular Wave Functions” J. Chem. Phys, 23; 1833–1840.
Perdew, JP, (1986a). “Density-functional approximation for the correlation energy of the inhomogeneous electron gas”. Phys. Rev. B, 33, 8822. (b) Perdew, JP, (1986b). Phys. Rev. B, 34, 7406.
Perdew, JP, Wang, Y. (1992). “Accurate and simple analytic representation of the electron-gas correlation energy”, Phys. Rev. B, 45, 13244.
Plech, T, Wujec, M, Kosikowsk, U, Malm, A, Rajtar, B, Polz-Dacewicz, M, (2013). “Synthesis and in vitro activity of 1,2,4-triazole-ciprofloxacin hybrids against drug-susceptible and drug-resistant bacteria”, Eur. J. Med. Chem. 60, 128-134.
Reed, AE, Curtiss, LA, Weinhold, F, (1988). “Intermolecular interactions from a natural bond orbital, donoracceptor viewpoint”, Chem Rev, 899.
Sumrra, SH, Kausar, S, Raza, MA, Zubair, M, Zafar, MN, Nadeem, MA, Mughal, EU, Chohan, ZH, Mushtaq, F, Rashid, U, (2018). “Metal based triazole compounds: their synthesis, computational, antioxidant, enzyme inhibition and antimicrobial properties”, J. Mol. Struct. 1168, 202-211.
Zhan, P, Li, D, Chen, X, Liu, X, De Clercq, E, (2011). “Functional roles of azoles motif in anti-HIV agents”, Curr. Med. Chem. 18, 29-46.