The Influence of C(sp3 )H-Selenium Interactions on the 77 Se NMR Quantification of the π-Accepting Properties of Carbenes

Angew Chem Int Ed Engl. 2020 Dec 1;59(49):22028-22033. doi: 10.1002/anie.202010744. Epub 2020 Sep 28.

Abstract

Selenium NMR has become a standard tool for scaling the π-accepting character of carbenes. Herein, we highlight that non-classical hydrogen bonding (NCHB), likely resulting from hyperconjugation, can play a significant role in the carbene-selenium 77 Se NMR chemical shift, thus triggering a non-linear behavior of the Se-Scale.

Keywords: N-heterocyclic carbenes; carbenes; cyclic alkyl amino carbenes; hydrogen bonding; selenium scale.