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Fluoride binding by an anionic receptor: Tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition

Fluoride binding by an anionic receptor: Tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition
Fluoride binding by an anionic receptor: Tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition

Here we report a family of bis-amide receptors for anion binding that contain carboxylic acid groups vicinal to the amide function. Deprotonation of the carboxylic acids decreases the acidity of amide NHs, switching on the anion binding ability of the deprotonated receptors with selectivity for fluoride complexation. The proposed systems represent a unique example of anionic receptors able to bind anions via H-bonding.

1359-7345
2745-2748
Montis, Riccardo
2d2d60eb-b455-414a-80d8-d5a58002bd92
Bencini, Andrea
71efef4c-46b3-4f0c-9520-9b001adedb08
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Conti, Luca
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Fusaro, Luca
c5263aa2-8b1b-4aaf-9469-68570e26d4a0
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Giorgi, Claudia
7451d537-a1c0-4b5c-b76c-dea547ad61f9
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Lippolis, Vito
d9833a14-4aab-4827-a2ba-be818871dcf5
Mapp, Lucy K.
b90136ce-37b0-464a-8934-d44a8c2d7e48
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0
Montis, Riccardo
2d2d60eb-b455-414a-80d8-d5a58002bd92
Bencini, Andrea
71efef4c-46b3-4f0c-9520-9b001adedb08
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Conti, Luca
047948a4-b543-4c1f-be36-8f59690917ed
Fusaro, Luca
c5263aa2-8b1b-4aaf-9469-68570e26d4a0
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Giorgi, Claudia
7451d537-a1c0-4b5c-b76c-dea547ad61f9
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Lippolis, Vito
d9833a14-4aab-4827-a2ba-be818871dcf5
Mapp, Lucy K.
b90136ce-37b0-464a-8934-d44a8c2d7e48
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0

Montis, Riccardo, Bencini, Andrea, Coles, Simon J., Conti, Luca, Fusaro, Luca, Gale, Philip A., Giorgi, Claudia, Horton, Peter N., Lippolis, Vito, Mapp, Lucy K. and Caltagirone, Claudia (2019) Fluoride binding by an anionic receptor: Tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition. Chemical Communications, 55 (19), 2745-2748. (doi:10.1039/c8cc09962f).

Record type: Article

Abstract

Here we report a family of bis-amide receptors for anion binding that contain carboxylic acid groups vicinal to the amide function. Deprotonation of the carboxylic acids decreases the acidity of amide NHs, switching on the anion binding ability of the deprotonated receptors with selectivity for fluoride complexation. The proposed systems represent a unique example of anionic receptors able to bind anions via H-bonding.

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More information

Accepted/In Press date: 14 January 2019
e-pub ahead of print date: 14 January 2019
Published date: 7 March 2019

Identifiers

Local EPrints ID: 430136
URI: https://eprints.soton.ac.uk/id/eprint/430136
ISSN: 1359-7345
PURE UUID: 7b8379fe-2ad6-4ae6-8c58-6ed3f51756f0
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

Catalogue record

Date deposited: 12 Apr 2019 16:30
Last modified: 17 Sep 2019 01:03

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Contributors

Author: Riccardo Montis
Author: Andrea Bencini
Author: Simon J. Coles ORCID iD
Author: Luca Conti
Author: Luca Fusaro
Author: Philip A. Gale ORCID iD
Author: Claudia Giorgi
Author: Peter N. Horton ORCID iD
Author: Vito Lippolis
Author: Lucy K. Mapp
Author: Claudia Caltagirone

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