Assessing the proton affinities of N, N′-diamidocarbenes

…, JP Moerdyk, GA Blake, CW Bielawski…

Index: Chen, Mu; Moerdyk, Jonathan P.; Blake, Garrett A.; Bielawski, Christopher W.; Lee, Jeehiun K. Journal of Organic Chemistry, 2013 , vol. 78, # 20 p. 10452 - 10458

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Citation Number: 7

Abstract

The gas-phase proton affinities (PAs) of a series of novel diamidocarbenes (DACs) were assessed and compared to various imidazolylidene-based N-heterocyclic carbenes (NHCs) through experimental and computational methods. Apart from a perfluorinated-phenyl derivative (PA= 233 kcal/mol), the calculated and measured PAs for a range of DACs (256– 261 kcal/mol) were comparable to those of the NHCs (260–266 kcal/mol). Proton transfer ...