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Molecular Conformational Analysis, Spectroscopic Characterization, Intramolecular Hydrogen Bonding and Natural Bond Analysis of (E,Z)-2-(4- Amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-triazole-1-yl)-N'- (thiophene-2-ylmethylene) Acetohydrazide

[ Vol. 16 , Issue. 3 ]

Author(s):

Abdurrahman Atalay*, Fatih Çelik, Yasemin Ünver, Kemal Sancak and Kamil Kaygusuz   Pages 215 - 225 ( 11 )

Abstract:


The optimized structural parameters and electronic properties including frontier molecular orbital (FMO) analysis, molecular electrostatic potential and NBO charge analysis of (E,Z)-2-(4- amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-triazole-1-yl)-N'-(thiophene-2-ylmethylene) acetohydrazide were investigated by using density functional theory (DFT) at B3LYP/6-311++G(d,p) level. The global reactivity parameters were evaluated in accordance with the energy values of HOMO and LUMO of each determined conformer. The molecule was experimentally characterized by means of FT-IR and NMR spectroscopic methods and also theoretically by B3LYP/6-311++G(d,p) and B3LYP/cc-pVTZ method (FT-IR and NMR, respectively). The theoretical results of spectroscopic analysis show good agreement with experimental outcomes. The natural bond orbital (NBO) analyses for studied conformers were performed at B3LYP/6-311++G(d,p) level to find hyperconjugative interactions as well as intramolecular hydrogen bond interaction. Besides, theoretical results indicate that the optimized structure of conformer E and Z possesses N‒H···N and N‒H···S weak hydrogen bonding, respectively.

Keywords:

DFT, conformational analysis, 1, 2, 4-triazole, NBO, intramolecular hydrogen bonding, NMR.

Affiliation:

Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080 Trabzon, Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080 Trabzon, Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080 Trabzon, Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080 Trabzon, Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080 Trabzon

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