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

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

doi:10.1039/C8CC09962F

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

Riccardo Montis,

‡*^a Andrea Bencini,

^b Simon J. Coles,

^c Luca Conti,

^b Luca Fusaro,

^d Philip A. Gale,

^e Claudia Giorgi,

^b Peter N. Horton,^c Vito Lippolis,

^a Lucy K. Mapp

^cf and Claudia Caltagirone

*^a

Author affiliations

* Corresponding authors

^a Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, S.S. 554 Bivio per Sestu, 09042 Monserrato (CA), Italy
E-mail: ccaltagirone@unica.it

^b Dipartimento di Chimica ‘Ugo Schiff’ Via della Lastruccia, 3-13 50019 Sesto Fiorentino (FI), Italy

^c Chemistry University of Southampton Highfield,, Southampton SO17 1BJ, UK

^d Université de Namur, rue de Bruxelles 61, B-5000 Namur, Belgium

^e F11 – School of Chemistry, The University of Sydney, NSW 2006, Australia

^f Johnson Matthey, 250 Cambridge Science Park, Cambridge CB4 0WE, UK

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.

Chemical Communications

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

Abstract

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

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