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Systematic experimental charge density analysis of anion receptor complexes

Systematic experimental charge density analysis of anion receptor complexes
Systematic experimental charge density analysis of anion receptor complexes
The first systematic electronic resolution study of a series of urea-based anion receptor complexes is presented. The hydrogen bonding in these multi-component systems was fully characterised using Bader’s Quantum Theory of Atoms In Molecules (QTAIM) with the strength of the various N?H…anion hydrogen bonds quantified and the individual contributions of different intermolecular forces to the overall receptor: anion interaction derived by comparison of the charge densities in the related complexes. The strength of the N?H…anion hydrogen bonds was correlated to the basicity of the anion and related to modifications applied to the structure of the receptors. The geometric criteria used to identify hydrogen bonding interactions in standard resolution X-ray diffraction studies were shown to be valid for stronger interactions. However, these geometric criteria are less reliable and lead to assumptions that are not necessarily upheld when applied to weaker intermolecular interactions and the presence of these could only be confirmed by charge density studies. The effect that changes to the receptor substitution pattern have on the entire supramolecular system is illustrated by the differences in the electrostatic potential distributions and atomic charges across the series. The application of systematic high resolution studies to rationalise a variety of host-guest systems has been demonstrated.
1463-9076
10943-10958
Kirby, Isabelle L.
5839d488-f346-4741-b757-9ecf30777938
Brightwell, Mark
3a48f3d5-dafa-4272-a505-4266f6e099c2
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Wilson, Claire
6be18134-9a9f-4d19-8197-0593a648773f
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Kirby, Isabelle L.
5839d488-f346-4741-b757-9ecf30777938
Brightwell, Mark
3a48f3d5-dafa-4272-a505-4266f6e099c2
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Wilson, Claire
6be18134-9a9f-4d19-8197-0593a648773f
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943

Kirby, Isabelle L., Brightwell, Mark, Pitak, Mateusz B., Wilson, Claire, Coles, Simon J. and Gale, Philip A. (2014) Systematic experimental charge density analysis of anion receptor complexes. Physical Chemistry Chemical Physics, 16, 10943-10958. (doi:10.1039/c3cp54858a).

Record type: Article

Abstract

The first systematic electronic resolution study of a series of urea-based anion receptor complexes is presented. The hydrogen bonding in these multi-component systems was fully characterised using Bader’s Quantum Theory of Atoms In Molecules (QTAIM) with the strength of the various N?H…anion hydrogen bonds quantified and the individual contributions of different intermolecular forces to the overall receptor: anion interaction derived by comparison of the charge densities in the related complexes. The strength of the N?H…anion hydrogen bonds was correlated to the basicity of the anion and related to modifications applied to the structure of the receptors. The geometric criteria used to identify hydrogen bonding interactions in standard resolution X-ray diffraction studies were shown to be valid for stronger interactions. However, these geometric criteria are less reliable and lead to assumptions that are not necessarily upheld when applied to weaker intermolecular interactions and the presence of these could only be confirmed by charge density studies. The effect that changes to the receptor substitution pattern have on the entire supramolecular system is illustrated by the differences in the electrostatic potential distributions and atomic charges across the series. The application of systematic high resolution studies to rationalise a variety of host-guest systems has been demonstrated.

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Accepted/In Press date: 18 November 2013
e-pub ahead of print date: 28 April 2014
Published date: 2014
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 364490
URI: http://eprints.soton.ac.uk/id/eprint/364490
ISSN: 1463-9076
PURE UUID: 86efb67e-c355-4457-90d6-454822b83ffe
ORCID for Mateusz B. Pitak: ORCID iD orcid.org/0000-0002-3680-7100
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

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Date deposited: 01 May 2014 15:30
Last modified: 15 Mar 2024 03:06

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Contributors

Author: Isabelle L. Kirby
Author: Mark Brightwell
Author: Mateusz B. Pitak ORCID iD
Author: Claire Wilson
Author: Simon J. Coles ORCID iD
Author: Philip A. Gale ORCID iD

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