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

Edwards, Peter R., Hiscock, Jennifer R., Gale, Philip A., Light, Mark E. (2010) Carbamate complexation by urea-based receptors: studies in solution and the solid state. Organic & Biomolecular Chemistry, 8 (1). pp. 100-106. ISSN 1477-0520. (doi:10.1039/B917140A) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided) (KAR id:70818)

The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided. (Contact us about this Publication)
Official URL
http://dx.doi.org/10.1039/B917140A

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.

Item Type: Article
DOI/Identification number: 10.1039/B917140A
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Sciences > School of Physical Sciences
Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Jennifer Hiscock
Date Deposited: 07 Dec 2018 16:06 UTC
Last Modified: 23 Jan 2020 04:15 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/70818 (The current URI for this page, for reference purposes)
Hiscock, Jennifer R.: https://orcid.org/0000-0002-1406-8802
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