Carboxylate binding in polar solvents using pyridylguanidinium salts
Carboxylate binding in polar solvents using pyridylguanidinium salts
A series of thiourea and guanidinium derivatives have been prepared and their ability to bind a carboxylate group has been investigated. Guanidinium 33, featuring two additional amides and a pyridine moiety, proved to be the most potent carboxylate binding site and was able to bind acetate in aqueous solvent systems (Kass = 480 M?1 in 30% H2O DMSO). The pyridine moiety is critical to obtaining strong binding, and comparison with the binding properties of analogous compounds in which the pyridine is replaced by a benzene ring provides a striking example of enthalpy–entropy compensation.
artificial receptors, water, enthalpy-entropy compensation, anion recognition, ligand-binding, aqueous solvents, amino-acid carboxylates, synthetic receptors, ala-d-ala, thermodynamic analysis
1706-1714
Fitzmaurice, R.J.
8901d558-95a8-4131-b903-c827c9686dd3
Gaggini, F.
d1bd5260-323b-4989-bab9-ee9404913901
Srinivasan, N.
ec85721a-8212-4f44-a230-b16e4b0664c2
Kilburn, J.D.
266a563a-6076-4109-9436-1c66d0b02383
2007
Fitzmaurice, R.J.
8901d558-95a8-4131-b903-c827c9686dd3
Gaggini, F.
d1bd5260-323b-4989-bab9-ee9404913901
Srinivasan, N.
ec85721a-8212-4f44-a230-b16e4b0664c2
Kilburn, J.D.
266a563a-6076-4109-9436-1c66d0b02383
Fitzmaurice, R.J., Gaggini, F., Srinivasan, N. and Kilburn, J.D.
(2007)
Carboxylate binding in polar solvents using pyridylguanidinium salts.
Organic & Biomolecular Chemistry, 5 (11), .
(doi:10.1039/b700988g).
Abstract
A series of thiourea and guanidinium derivatives have been prepared and their ability to bind a carboxylate group has been investigated. Guanidinium 33, featuring two additional amides and a pyridine moiety, proved to be the most potent carboxylate binding site and was able to bind acetate in aqueous solvent systems (Kass = 480 M?1 in 30% H2O DMSO). The pyridine moiety is critical to obtaining strong binding, and comparison with the binding properties of analogous compounds in which the pyridine is replaced by a benzene ring provides a striking example of enthalpy–entropy compensation.
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Published date: 2007
Keywords:
artificial receptors, water, enthalpy-entropy compensation, anion recognition, ligand-binding, aqueous solvents, amino-acid carboxylates, synthetic receptors, ala-d-ala, thermodynamic analysis
Identifiers
Local EPrints ID: 54296
URI: http://eprints.soton.ac.uk/id/eprint/54296
ISSN: 1477-0520
PURE UUID: 5d1cd976-1b2d-4098-aa29-89b9e7f06486
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Date deposited: 31 Jul 2008
Last modified: 15 Mar 2024 10:46
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Contributors
Author:
R.J. Fitzmaurice
Author:
F. Gaggini
Author:
N. Srinivasan
Author:
J.D. Kilburn
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