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Experimental and theoretical charge distribution in (Z)-N-methyl-C-phenylnitrone

Experimental and theoretical charge distribution in (Z)-N-methyl-C-phenylnitrone
Experimental and theoretical charge distribution in (Z)-N-methyl-C-phenylnitrone
The total experimental charge density in (Z)-N-methyl-C-phenylnitrone (1) has been determined using high-resolution X-ray diffraction data in combination with neutron diffraction data measured at 100 K in terms of the rigid pseudoatom model. Multipole refinement converged at R = 0.03 for 7163 reflections with I > 2sigma(I). Topological analysis of the total experimental charge density rho(r) and its Laplacian, del(2)rho(r) and a comparison with high level theoretical gas-phase calculations reveals an unexpected electron distribution in the N-O group, both atoms having negative atomic charges, contrary to that commonly assumed in nitrone species. This observation is confirmed on examination of both the theoretical charges and the molecular electrostatic potential. Compound 1 contains a large number of hydrogen bonds and these are analysed using the atoms in molecules approach leading to quantitative values for bond strength, ranging from medium to very weak.
nitrones
1477-0520
1034-1040
Hibbs, David E.
92245583-6eb5-4afc-9093-57377cd6abf4
Hanrahan, Jane R.
dffb099d-2870-4871-8454-fadea05bea8a
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Knight, David W.
9ac3922f-85d8-4cbe-a26d-2f24c7b9716d
Overgaard, Jacob
23136956-25b6-4dfe-b579-5dd1157c16d8
Turner, Peter
af5f357d-f9f5-42fc-a739-761653b4cb87
Piltz, Ross O.
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Waller, Mark P.
82f730f4-4ff8-4795-9737-613db06dcc75
Hibbs, David E.
92245583-6eb5-4afc-9093-57377cd6abf4
Hanrahan, Jane R.
dffb099d-2870-4871-8454-fadea05bea8a
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Knight, David W.
9ac3922f-85d8-4cbe-a26d-2f24c7b9716d
Overgaard, Jacob
23136956-25b6-4dfe-b579-5dd1157c16d8
Turner, Peter
af5f357d-f9f5-42fc-a739-761653b4cb87
Piltz, Ross O.
46bdd697-b794-41e5-b1bb-a9f7106b8a9e
Waller, Mark P.
82f730f4-4ff8-4795-9737-613db06dcc75

Hibbs, David E., Hanrahan, Jane R., Hursthouse, Michael B., Knight, David W., Overgaard, Jacob, Turner, Peter, Piltz, Ross O. and Waller, Mark P. (2003) Experimental and theoretical charge distribution in (Z)-N-methyl-C-phenylnitrone. Organic & Biomolecular Chemistry, 1 (6), 1034-1040. (doi:10.1039/b210698a).

Record type: Article

Abstract

The total experimental charge density in (Z)-N-methyl-C-phenylnitrone (1) has been determined using high-resolution X-ray diffraction data in combination with neutron diffraction data measured at 100 K in terms of the rigid pseudoatom model. Multipole refinement converged at R = 0.03 for 7163 reflections with I > 2sigma(I). Topological analysis of the total experimental charge density rho(r) and its Laplacian, del(2)rho(r) and a comparison with high level theoretical gas-phase calculations reveals an unexpected electron distribution in the N-O group, both atoms having negative atomic charges, contrary to that commonly assumed in nitrone species. This observation is confirmed on examination of both the theoretical charges and the molecular electrostatic potential. Compound 1 contains a large number of hydrogen bonds and these are analysed using the atoms in molecules approach leading to quantitative values for bond strength, ranging from medium to very weak.

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More information

Published date: 2003
Keywords: nitrones

Identifiers

Local EPrints ID: 19981
URI: http://eprints.soton.ac.uk/id/eprint/19981
ISSN: 1477-0520
PURE UUID: c703f741-6b72-414e-8083-cf6604fce7f1

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Date deposited: 24 Feb 2006
Last modified: 15 Mar 2024 06:21

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Contributors

Author: David E. Hibbs
Author: Jane R. Hanrahan
Author: David W. Knight
Author: Jacob Overgaard
Author: Peter Turner
Author: Ross O. Piltz
Author: Mark P. Waller

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