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

A one-dimensional silver(I) coordination polymer based on an asymmetric flexibleN-donor carboxylate ligand:catena-poly[(μ3-4-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}benzoato-κ3O:O′:N4)silver(I)]

“…angle between the planes of the central tetrazole ring and the attached phenyl ring is 41.16 16, which is smaller than that found in free Hptmba [61.66 11; Zhang et al, 2012], but which still indicates that interannular conjugation is insignificant or absent. As shown in Fig.…”

“…All chemicals were purchased from commercial sources (Alfa-Aesar) and were used without further purification. 4-{[(1-Phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}benzoic acid (Hptmba) was synthesized according to our previously reported method (Zhang et al, 2012). For the preparation of (I), a solution of silver nitrate (0.085 g, 0.5 mmol) in aceto-nitrile (5 ml) was carefully layered onto an aqueous solution (5 ml) of Hptmba (0.156 g, 0.5 mmol) and triethylamine (0.051 g, 0.5 mmol).…”

“…However, less attention has hitherto been focused on flexible ligands, especially on asymmetric flexible bridges (Wei et al, 2009). In this work, we selected the asymmetric flexible N-donor ligand 4-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}benzoate (ptmba À ; Zhang et al, 2012), which has at least three expected advantages: (i) a strong coordination ability from the combination of carboxylate and tetrazole groups; (ii) a flexible conformation (due to the -SCH 2 -group) and an asymmetric character; (iii) potentially rich supramolecular interactions, such as hydrogen bonds,stacking and/or C-HÁ Á Á interactions etc. Herein, we report the synthesis and crystal structure of the resulting one-dimensional silver(I) coordination polymer, [Ag(ptmba)] n , (I), and discuss its thermal stability and luminescence properties.…”

A new one-dimensional nickel metal–organic framework:catena-poly[[[diaquabis(4-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}benzoato-κO)nickel(II)]-μ-4,4′-bipyridine-κ2N:N′] monohydrate]

“…(1-Phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}benzoic acid (HL) was prepared according to our previously reported method (Zhang et al, 2012). For the synthesis of (I), a mixture of NiCl 2 Á6H 2 O (23.8 mg, 0.1 mmol), HL (62.4 mg, 0.2 mmol) and 4,4 0 -bipyridine (15.6 mg, 0.1 mmol) in H 2 O (10 ml) was placed in a Teflon-lined stainless steel vessel, heated at 393 K for 3 d and then cooled to room temperature.…”