N-substituted bis(tetrazol-5-yl)diazenes: Synthesis, spectra, X-ray molecular and crystal structures, and quantum-chemical DFT calculations

✍ Scribed by Tatiyana V. Serebryanskaya; Vadim E. Matulis; Alexander S. Lyakhov; Sergei V. Voitekhovich,; Pavel N. Gaponik; Oleg A. Ivashkevich

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 477 KB
• Volume: 21
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20574

✦ Synopsis

Abstract

N‐Substituted bis(tetrazol‐5‐yl)diazenes (substituents are 1‐CH~3~ (3a), 1‐Ph (3b), 2‐CH~3~ (3c), and 2‐^t^Bu (3d)) were synthesized by oxidative coupling of corresponding 5‐aminotetrazoles. All compounds were characterized with ^1^H and ^13^C NMR, IR‐ and UV‐spectroscopy, and thermal analysis. Crystal and molecular structures of bis(1‐phenyltetra‐ zol‐5‐yl)diazene (3b) and bis(2‐tert‐butyltetrazol‐5‐yl)diazene (3d) were determined by single crystal X‐ray diffraction. Molecules of these compounds are trans‐isomers in solid. According to X‐Ray data, 3b molecule is S‐trans‐S‐trans conformer, however 3d is S‐cis‐S‐cis one. Quantum‐chemical investigation of geometry and relative stability of cis‐ and trans‐isomers and stable conformations of compounds 3a–d was carried out. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:24–35, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20574