Issue 7, 2003
From the journal:

Organic & Biomolecular Chemistry

X–N Charge density analysis of the hydrogen bonding motif in 1-(2-hydroxy-5-nitrophenyl)ethanone†

David E. Hibbs,*a   Jacob Overgaarda  and  Ross O. Piltzb  

* Corresponding authors

a School of Chemistry, University of Sydney, Sydney, NSW 2006, Australia
E-mail: d.hibbs@chem.usyd.edu.au
Fax: +61 (0) 2 9351 3329
Tel: +61 (0) 2 9036 9122

b Neutron Scattering Section, Australian Nuclear Science and Technology Organisation, PMB 1, Menai, NSW 2234, Australia
E-mail: rop@ansto.gov.au
Fax: +61(0) 2 9717 3606
Tel: +61 (0) 2 9717 3607

Abstract

The total experimental charge density in 1-(2-hydroxy-5-nitrophenyl)ethanone (1) has been determined using high-resolution X-ray diffraction data in combination with neutron diffraction data measured at 100 K. Multipole refinement was carried out in terms of the rigid pseudoatom model. Multipole refinement converged at R = 0.026 for 5415 reflections with I > 2σ(I). Topological analysis of the total experimental charge density ρ(r) and its Laplacian, −∇2ρ(r) together with a comparison against high level theoretical gas-phase calculations reveals fine details of intra- and intermolecular bonding features, in particular the extent of the π-delocalisation throughout the molecule.

Graphical abstract: X–N Charge density analysis of the hydrogen bonding motif in 1-(2-hydroxy-5-nitrophenyl)ethanone

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Article information

DOI
https://doi.org/10.1039/B211683A
Article type
Paper
Submitted
25 Nov 2002
Accepted
03 Feb 2003
First published
03 Mar 2003

Org. Biomol. Chem., 2003,1, 1191-1198

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X–N Charge density analysis of the hydrogen bonding motif in 1-(2-hydroxy-5-nitrophenyl)ethanone

D. E. Hibbs, J. Overgaard and R. O. Piltz, Org. Biomol. Chem., 2003, 1, 1191 DOI: 10.1039/B211683A

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