Proton affinities of N-heterocyclic carbene super bases

Hao Chen, Dina R. Justes, R. Graham Cooks

Research output: Contribution to journalArticlepeer-review

89 Scopus citations


(Chemical Equation Presented) The gas-phase proton affinity of the N-heterocyclic carbene, 1-ethyl-3-methylimidazol-2-ylidene, was determined to be 251.3 ± 4 kcal/mol using the kinetic method, a value which makes the carbene one of the strongest bases reported thus far. Density functional theory calculations have been carried out at the B3LYP/6-31+G(d) level to compare the high experimental value with that estimated theoretically. Experimental results also show that two other N-heterocyclic carbenes with larger substituents have even higher proton affinities.

Original languageEnglish (US)
Pages (from-to)3949-3952
Number of pages4
JournalOrganic Letters
Issue number18
StatePublished - Sep 1 2005
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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