Abstract
(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 language | English (US) |
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Pages (from-to) | 3949-3952 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 7 |
Issue number | 18 |
DOIs | |
State | Published - Sep 1 2005 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry