1,6;2,3-Bis-BN Cyclohexane: Synthesis, Structure, and Hydrogen Release

J Am Chem Soc. 2022 May 18;144(19):8434-8438. doi: 10.1021/jacs.1c13581. Epub 2022 Apr 21.

Abstract

BN/CC isosterism has been widely investigated as a strategy to expand carbon-based compounds. The introduction of BN units in organic molecules always results in novel properties. In this work, we reported the first synthesis and characterization of 1,6;2,3-bis-BN cyclohexane, an isostere of cyclohexane with two adjacent BN pairs. Its ring flipping barrier is similar to that of cyclohexane. Protic hydrogens on N in 1,6;2,3-bis-BN cyclohexane show higher reactivity than its isomeric bis-BN cyclohexane. This compound exhibits an appealing hydrogen storage capability of >9.0 wt %, nearly twice as much as the 1,2;4,5-bis-BN cyclohexane.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclohexanes*
  • Hydrogen*

Substances

  • Cyclohexanes
  • Hydrogen