On the interaction between N-heterocyclic carbenes and organic acids: Structural authentication of the first N-H···C hydrogen bond and remarkably short C-H···O interactions

John A. Cowan; Jason A.C. Clyburne; Matthew G. Davidson; R. Luke W. Harris; Judith A.K. Howard; Patrick Küpper; Michael A. Leech; Stephen P. Richards

doi:10.1002/1521-3773(20020415)41:8<1432::AID-ANIE1432>3.0.CO;2-M

On the interaction between N-heterocyclic carbenes and organic acids: Structural authentication of the first N-H···C hydrogen bond and remarkably short C-H···O interactions

John A. Cowan, Jason A.C. Clyburne, Matthew G. Davidson, R. Luke W. Harris, Judith A.K. Howard, Patrick Küpper, Michael A. Leech, Stephen P. Richards

Department of Chemistry

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

102 Citations (SciVal)

Abstract

Two unprecedented hydrogen bonds were observed in the adducts obtained by the reactions of an N-heterocyclic carbene with a bulky phenol and with diphenylamine. In the former case, proton transfer yields an imidazolium aryloxide (1) containing the shortest C-H···O interaction seen to date and in the latter, the hydrogen atom remains bound to the organic acid but forms a unique N-H···C hydrogen bond (2).

Original language	English
Pages (from-to)	1432-1434
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	8
DOIs	https://doi.org/10.1002/1521-3773(20020415)41:8<1432::AID-ANIE1432>3.0.CO;2-M
Publication status	Published - 15 Apr 2002

Keywords

Carbenes
Hydrogen bonds
Pi interactions
Structure elucidation

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/1521-3773(20020415)41:8<1432::AID-ANIE1432>3.0.CO;2-M

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Cowan, J. A., Clyburne, J. A. C., Davidson, M. G., Harris, R. L. W., Howard, J. A. K., Küpper, P., Leech, M. A., & Richards, S. P. (2002). On the interaction between N-heterocyclic carbenes and organic acids: Structural authentication of the first N-H···C hydrogen bond and remarkably short C-H···O interactions. Angewandte Chemie - International Edition, 41(8), 1432-1434. https://doi.org/10.1002/1521-3773(20020415)41:8<1432::AID-ANIE1432>3.0.CO;2-M

On the interaction between N-heterocyclic carbenes and organic acids: Structural authentication of the first N-H···C hydrogen bond and remarkably short C-H···O interactions. / Cowan, John A.; Clyburne, Jason A.C.; Davidson, Matthew G. et al.
In: Angewandte Chemie - International Edition, Vol. 41, No. 8, 15.04.2002, p. 1432-1434.

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

Cowan, JA, Clyburne, JAC, Davidson, MG, Harris, RLW, Howard, JAK, Küpper, P, Leech, MA & Richards, SP 2002, 'On the interaction between N-heterocyclic carbenes and organic acids: Structural authentication of the first N-H···C hydrogen bond and remarkably short C-H···O interactions', Angewandte Chemie - International Edition, vol. 41, no. 8, pp. 1432-1434. https://doi.org/10.1002/1521-3773(20020415)41:8<1432::AID-ANIE1432>3.0.CO;2-M

Cowan JA, Clyburne JAC, Davidson MG, Harris RLW, Howard JAK, Küpper P et al. On the interaction between N-heterocyclic carbenes and organic acids: Structural authentication of the first N-H···C hydrogen bond and remarkably short C-H···O interactions. Angewandte Chemie - International Edition. 2002 Apr 15;41(8):1432-1434. doi: 10.1002/1521-3773(20020415)41:8<1432::AID-ANIE1432>3.0.CO;2-M

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abstract = "Two unprecedented hydrogen bonds were observed in the adducts obtained by the reactions of an N-heterocyclic carbene with a bulky phenol and with diphenylamine. In the former case, proton transfer yields an imidazolium aryloxide (1) containing the shortest C-H···O interaction seen to date and in the latter, the hydrogen atom remains bound to the organic acid but forms a unique N-H···C hydrogen bond (2).",

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AU - Davidson, Matthew G.

AU - Harris, R. Luke W.

AU - Howard, Judith A.K.

AU - Küpper, Patrick

AU - Leech, Michael A.

AU - Richards, Stephen P.

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AB - Two unprecedented hydrogen bonds were observed in the adducts obtained by the reactions of an N-heterocyclic carbene with a bulky phenol and with diphenylamine. In the former case, proton transfer yields an imidazolium aryloxide (1) containing the shortest C-H···O interaction seen to date and in the latter, the hydrogen atom remains bound to the organic acid but forms a unique N-H···C hydrogen bond (2).

KW - Carbenes

KW - Hydrogen bonds

KW - Pi interactions

KW - Structure elucidation

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On the interaction between N-heterocyclic carbenes and organic acids: Structural authentication of the first N-H···C hydrogen bond and remarkably short C-H···O interactions

Abstract

Keywords

ASJC Scopus subject areas

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