An experimental and computational investigation of the formation and structures of N-hydro and N,N'-dihydro-benzo-2,1,3-chalcogenadiazolium chlorides

Lucia M. Lee, Philip J.W. Elder, Anthony F. Cozzolino, Qin Yang, Ignacio Vargas-Baca

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

The conjugate acids of benzo-2,1,3-selena- and benzo-2,1,3-telluradiazole are the simplest members of the family of N-substituted chalcogenadiazolium cations. Four crystalline phases that in principle contain such molecular ions were isolated and structurally characterized: C6H4(NH) 2TeCl2, [C6H5(NH)] 3[C6H4(NH)2TeCl4]Cl, C6H4N(NH)SeCl and C6H4N(NH)SeCl · 1/2 [H5O2]Cl. The stepwise protonation of benzo-2,1,3-teluradiazole in DMSO solution was monitored by 1H NMR, providing an estimate of the basicity of this molecule relative to pyridine. While most of the structures are consistent with the chalcogen in oxidation state II, the molecular geometry of C6H4(NH) 2TeCl4 is suggestive of oxidation state IV. The relationship between the two structural types was examined with DFT calculations.

Original languageEnglish
Pages (from-to)117-133
Number of pages17
JournalMain Group Chemistry
Volume9
Issue number1-2
DOIs
StatePublished - 2010

Keywords

  • DFT calculations
  • Heterocycles
  • acid-base properties
  • chalcogens
  • heterocyclic cations
  • molecular structure

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