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Carbamate complexation by urea-based receptors: studies in solution and the solid state

Carbamate complexation by urea-based receptors: studies in solution and the solid state
Carbamate complexation by urea-based receptors: studies in solution and the solid state
The interactions of a series of urea based neutral hydrogen bond donor anion receptors have been investigated with i) alkylcarbamate anions formed by the reaction of carbon dioxide with primary aliphatic amines and ii) the zwitterionic species formed by the reaction of carbon dioxide with 1,4,5,6-tetrahydropyrimidine. Significant downfield chemical shift changes were observed for the urea NH protons in many cases, consistent with host:anion hydrogen bonding interactions, and thus stabilisation of the carbon dioxide bound species. In the case of the alkylammonium-alkylcarbamate salts, this represents successful competition with electrostatic interactions between the alkylcarbamate and alkylammonium components of the salt. A synchrotron structure of a ternary complex formed by an amide appended diindolylurea, the ammonium carbamate salt formed by 1,3-diaminopropane and CO2 and 18-crown-6, was elucidated and shows the carbamate group bound by six hydrogen bonds (accepting five and donating one) to the functionalised diindolylurea.
1477-0520
100-106
Edwards, Peter R.
aaa0f75a-0fd5-490a-ba73-a420189e4695
Hiscock, Jennifer R.
99a8a34c-a869-48e2-b713-1e69e4741032
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Edwards, Peter R.
aaa0f75a-0fd5-490a-ba73-a420189e4695
Hiscock, Jennifer R.
99a8a34c-a869-48e2-b713-1e69e4741032
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161

Edwards, Peter R., Hiscock, Jennifer R., Gale, Philip A. and Light, Mark E. (2010) Carbamate complexation by urea-based receptors: studies in solution and the solid state. Organic & Biomolecular Chemistry, 8 (1), 100-106. (doi:10.1039/b917140a).

Record type: Article

Abstract

The interactions of a series of urea based neutral hydrogen bond donor anion receptors have been investigated with i) alkylcarbamate anions formed by the reaction of carbon dioxide with primary aliphatic amines and ii) the zwitterionic species formed by the reaction of carbon dioxide with 1,4,5,6-tetrahydropyrimidine. Significant downfield chemical shift changes were observed for the urea NH protons in many cases, consistent with host:anion hydrogen bonding interactions, and thus stabilisation of the carbon dioxide bound species. In the case of the alkylammonium-alkylcarbamate salts, this represents successful competition with electrostatic interactions between the alkylcarbamate and alkylammonium components of the salt. A synchrotron structure of a ternary complex formed by an amide appended diindolylurea, the ammonium carbamate salt formed by 1,3-diaminopropane and CO2 and 18-crown-6, was elucidated and shows the carbamate group bound by six hydrogen bonds (accepting five and donating one) to the functionalised diindolylurea.

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Published date: January 2010

Identifiers

Local EPrints ID: 144899
URI: http://eprints.soton.ac.uk/id/eprint/144899
ISSN: 1477-0520
PURE UUID: 368fd6c1-063a-44cd-8b1a-fa28148b0797
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 15 Apr 2010 13:55
Last modified: 07 Oct 2020 07:25

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