Stabilisation of alkylcarbamate anions using neutral hydrogen bond donors
Stabilisation of alkylcarbamate anions using neutral hydrogen bond donors
The interactions of a series of urea-based anion receptors and alkylcarbamate species formed by the reaction of carbon dioxide with primary amines have been investigated by 1H NMR. Significant downfield shifts in the NH proton signals of the receptors in the presence of the alkylcarbamates were observed, consistent with classical host:anion hydrogen-bonding. This observation demonstrates that neutral hydrogen bond donor receptors can compete with ammonium cations to bind carbamates in DMSO-d6 solution.
carbamate, carbon dioxide, anion binding, hydrogen-bonding
4922-4924
Edwards, Peter R.
aaa0f75a-0fd5-490a-ba73-a420189e4695
Hiscock, Jennifer R.
99a8a34c-a869-48e2-b713-1e69e4741032
Gale, Philip A.
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26 August 2009
Edwards, Peter R.
aaa0f75a-0fd5-490a-ba73-a420189e4695
Hiscock, Jennifer R.
99a8a34c-a869-48e2-b713-1e69e4741032
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Edwards, Peter R., Hiscock, Jennifer R. and Gale, Philip A.
(2009)
Stabilisation of alkylcarbamate anions using neutral hydrogen bond donors.
Tetrahedron Letters, 50 (34), .
(doi:10.1016/j.tetlet.2009.06.058).
Abstract
The interactions of a series of urea-based anion receptors and alkylcarbamate species formed by the reaction of carbon dioxide with primary amines have been investigated by 1H NMR. Significant downfield shifts in the NH proton signals of the receptors in the presence of the alkylcarbamates were observed, consistent with classical host:anion hydrogen-bonding. This observation demonstrates that neutral hydrogen bond donor receptors can compete with ammonium cations to bind carbamates in DMSO-d6 solution.
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Published date: 26 August 2009
Keywords:
carbamate, carbon dioxide, anion binding, hydrogen-bonding
Identifiers
Local EPrints ID: 144911
URI: http://eprints.soton.ac.uk/id/eprint/144911
ISSN: 0040-4039
PURE UUID: 4424394c-3e49-441f-b7aa-fd2c4ae03b01
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Date deposited: 15 Apr 2010 12:51
Last modified: 14 Mar 2024 02:44
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Author:
Peter R. Edwards
Author:
Jennifer R. Hiscock
Author:
Philip A. Gale
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