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Stabilisation of alkylcarbamate anions using neutral hydrogen bond donors

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
0040-4039
4922-4924
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.
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), 4922-4924. (doi:10.1016/j.tetlet.2009.06.058).

Record type: Article

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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More information

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
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

Catalogue record

Date deposited: 15 Apr 2010 12:51
Last modified: 26 Nov 2019 01:53

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