STRUCTURAL FEATURES OF 2-(4,5-DIPHENYL-4H-1,2,4-TRIAZOL-3-YL)THIO)-1-(3-METHYL-3-PHENYLCYCLOBUTYL) ETHANONE: X-RAY DIFFRACTION AND DFT CALCULATIONS

Abstract

ABSTRACT This paper reported that the combined X-ray diffraction and DFT computational study on molecular structure of the title compound, [C 27 H 25 N 3 O 2 S]. The com -pound contains a cyclobutane, a triazole and three phenyl rings. The molecular geometry of the compound was brought to light by X-ray single crystal structure de -termination. X-ray study shows that the title compound has a weak intermolecular C—O ···π interaction as well as many D—H ···A and D—H ···π hydrogen bonds. The initial guess on the compound was first obtained from the X-ray coordinates which were optimized by Density Functional Theory (DFT)/B3LYP method with 6-31G(d, p) and 6-31G+(d, p) as basis sets. DFT electronic structures were compared to the experimentally determined molecular structure in the solid state.e-mail: fatihsen55@gmail.com ) INTRODUCTION In recent years, the synthesis and structural investigation 1,2,4-triazole derivatives have attracted considerable attention because of their pharmacological and biological properties such as antibacterial [1-3], antidepressant [4], antitubercular [5], analgesic [6], antiviral [7], etc. Cyclobutane itself is of no commercial or biological significance, but more complex derivatives are important in biology and biotechnology [8]. It is well known that 3-substituted cyclobutane carboxylic acid derivatives exhibit anti-inflammatory and anti-depressant activity [9], and also liquid crystal properties [10]. When these effects are taken into account, compounds containing 1,2,4-triazole and cyclobutane rings has become more remarkable. In this study, a novel compound named as 2-((4,5-diphenyl-4H-1,2,4-triazol-3-yl)thio)-1-(3-methyl-3-phenylcyclobutyl)ethanone is firstly synthesized in our laboratories by us. Previously, we have reported the cyclobutane derivatives compound [11-12]. The difference of this study from the other studies, the molecular structure of the compound is supported by theoretical studies. Because it is given good results in the calculation of the molecular geometry, density functional theory (DFT) method was used in the theoretical calculations.Our work makes up of the synthesis, X-ray molecular structure analysis and Density Functional Theory (DFT) studies of the title compound.The molecular structure of the title compound brought to light by X-ray diffraction. The initial guess of the compound was first obtained from the X-ray coordinates was optimized by DFT/B3LYP method with 6-31G(d, p) and 6-31G+(d, p) as basis sets. The calculated geometric parameters (bond lengths, bond angles and torsion angles) of theoretical structures were compared with their experimental data.