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

Activation of Ammonia by a Carbene-Stabilized Dithiolene Zwitterion

Yuzhong Wang  1 , Phuong M Tran  1 , Mitchell E Lahm  1 , Yaoming Xie  1 , Pingrong Wei  1 , Earle R Adams  1 , John N Glushka  1 , Zichun Ren  1 , Vladimir V Popik  1 , Henry F Schaefer 3rd  1 , Gregory H Robinson  1
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Activation of Ammonia by a Carbene-Stabilized Dithiolene Zwitterion

Yuzhong Wang et al. J Am Chem Soc. .

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.

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