Activation of Ammonia by a Carbene-Stabilized Dithiolene Zwitterion

J Am Chem Soc. 2022 Sep 14;144(36):16325-16331. doi: 10.1021/jacs.2c07920. Epub 2022 Aug 29.

Abstract

A carbene-stabilized dithiolene zwitterion (3) activates ammonia, affording 4 and 5, through both single-electron transfer (SET) and hydrogen atom transfer (HAT). Reaction products were characterized spectroscopically and by single-crystal X-ray diffraction. The mechanism of the formation of 4 and 5 was probed by experimental and computational methods. This discovery is the first example of metal-free ammonia activation via HAT.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Ammonia*
  • Electron Transport
  • Hydrogen* / chemistry
  • Methane / analogs & derivatives

Substances

  • carbene
  • Ammonia
  • Hydrogen
  • Methane