Mesoionic tetrazolium-5-aminides: Synthesis, Molecular and Crystal Structures, UV-Vis Spectra, and DFT Calculations

  1. Vladislav A. BudevichORCID Logo,
  2. Sergei V. VoitekhovichORCID Logo,
  3. Alexander V. ZuraevORCID Logo,
  4. Vadim E. Matulis,
  5. Vitaly E. MatulisORCID Logo,
  6. Alexander S. Lyakhov,
  7. Ludmila S. Ivashkevich and
  8. Oleg A. Ivashkevich

Submitting author affiliation: Research Institute for Physical Chemical Problems of Belarusian State University, Minsk, Belarus

Beilstein Arch. 2020, 2020122. https://doi.org/10.3762/bxiv.2020.122.v1

Published 22 Oct 2020

  • Preprint

Abstract

Tetrazolium-5-aminides have been prepared by tert-butylation of 5-aminotetrazole and its N-methyl derivatives by t-BuOH/HClO4 system followed by treatment of tetrazolium salts by alkali. These mesoionic compounds have been found to show higher reactivity of exocyclic N atom in comparison with 5-aminotetrazoles. They react with 1,2-dibromoethane and 5-(methylsulfonyl)-1-phenyl-1H-tetrazole and substitute bromine and methylsulfonyl groups giving tetrazolium salts or conjugate aminides. Obtained mesoionic tetrazoles have been characterized by elemental analysis, FT-IR, NMR and UV-Vis spectroscopy, TGA/DSC analysis and for 1,3-di-tert-butyltetrazolium-5-aminide, it’s N,N’-ethylene bridged bis-derivative and (1,3-di-tert-butyl-1H-tetrazol-3-ium-5-yl)(1-phenyl-1H-tetrazol-5-yl)amide by single crystal X-ray analysis. Structural and spectral features of tetrazolium-5-aminides are discussed by using quantum-chemical calculations.

Keywords: Aminotetrazoles; DFT; Mesoionic compounds; UV-Vis spectra; X-ray analysis

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Budevich, V. A.; Voitekhovich, S. V.; Zuraev, A. V.; Matulis, V. E.; Matulis, V. E.; Lyakhov, A. S.; Ivashkevich, L. S.; Ivashkevich, O. A. Beilstein Arch. 2020, 2020122. doi:10.3762/bxiv.2020.122.v1

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