Synthesis, crystal structure, spectral characterization, and DFT studies on 4-((1-phenyl-1H-tetrazol-5-ylthio)methyl)benzoic acid

Abstract

A new thiotetrazole compound, 4-((1-phenyl-1H-tetrazol-5-ylthio)methyl) benzoic acid (1), has been synthesized and characterized by elemental analysis, 1H and 13C NMR, ESI-MS, FT-IR, UV–vis, fluorescence spectra, and single-crystal X-ray diffraction analysis. The structural analysis reveals that compound 1 adopts a nonplanar geometric structure and exhibits an extensive but not uniform π delocalization with all members of the tetrazolyl ring and the exocyclic sulfur atom. A density functional theory (DFT) calculation at B3LYP/6-31G** level of theory was performed to elucidate the structure of this thiotetrazole system. And the time-dependent DFT (TD-DFT) calculations of absorption spectra reveal two electron-transition bands derived from the contribution of π → π* transitions, which are in agreement with experimental results. Moreover, compound 1 exhibits a blue-light emission (λem = 441 nm) in the solid state at room temperature. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:435–443, 2012; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21034