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Experimental evidence of Chalcogen bonding at oxygen

Abstract

An o-nitro-O-aryl oxime was observed to exhibit a short O...O contact, which exhibited characteristics consistent with a chalcogen bond. Topological analysis of the experimental electron density of two analogues shows the presence of a bond path between the two oxygen atoms, with r(r) and Ñ2r(r) value consistent with an electrostatic interaction. NBO calculations indicate the presence of a small n(O) s* (O-N) orbital delocalisation worth 1.13 kcal/mol. Finally, electrostatic potential calculations indicate the presence of a s-hole, the "smoking gun" indicating a Ch bond. These results are unusual as oxygen is not typically considered to be a Ch-bond donor, especially in relatively unactivated systems such as oximes.

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Article information


Submitted
23 Dec 2019
Accepted
13 Feb 2020
First published
13 Feb 2020

Chem. Commun., 2020, Accepted Manuscript
Article type
Communication

Experimental evidence of Chalcogen bonding at oxygen

T. Fellowes, B. L. Harris and J. White, Chem. Commun., 2020, Accepted Manuscript , DOI: 10.1039/C9CC09896H

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