Proton affinities of N-heterocyclic carbene super bases

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

doi:10.1021/ol0514247

Proton affinities of N-heterocyclic carbene super bases

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

Research output: Contribution to journal › Article › peer-review

91 Scopus citations

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)
Pages (from-to)	3949-3952
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	18
DOIs	https://doi.org/10.1021/ol0514247
State	Published - Sep 1 2005
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol0514247

Cite this

@article{7d076cd9f7c34d6fad2753535a0d9c09,

title = "Proton affinities of N-heterocyclic carbene super bases",

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.",

author = "Hao Chen and Justes, \{Dina R.\} and Cooks, \{R. Graham\}",

year = "2005",

month = sep,

day = "1",

doi = "10.1021/ol0514247",

language = "English (US)",

volume = "7",

pages = "3949--3952",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Proton affinities of N-heterocyclic carbene super bases

AU - Chen, Hao

AU - Justes, Dina R.

AU - Cooks, R. Graham

PY - 2005/9/1

Y1 - 2005/9/1

N2 - (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.

AB - (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.

UR - https://www.scopus.com/pages/publications/24944586038

UR - https://www.scopus.com/inward/citedby.url?scp=24944586038&partnerID=8YFLogxK

U2 - 10.1021/ol0514247

DO - 10.1021/ol0514247

M3 - Article

C2 - 16119939

AN - SCOPUS:24944586038

SN - 1523-7060

VL - 7

SP - 3949

EP - 3952

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Proton affinities of N-heterocyclic carbene super bases

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this