Issue 22, 2020

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. The O–N bond length of the oxime was appreciably longer than the expected value, and NBO calculations indicated the presence of a n(O) → σ(O–N) orbital delocalisation. Topological analysis of the experimental electron density of two analogues shows the presence of a bond path between the two oxygen atoms, with ρ(r) and ∇2ρ(r) values consistent with an electrostatic interaction. Finally, electrostatic potential calculations indicate the presence of a σ-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 unactivated systems such as oximes.

Graphical abstract: Experimental evidence of chalcogen bonding at oxygen

Supplementary files

Article information

Article type
Communication
Submitted
23 Dec 2019
Accepted
13 Feb 2020
First published
13 Feb 2020

Chem. Commun., 2020,56, 3313-3316

Experimental evidence of chalcogen bonding at oxygen

T. Fellowes, B. L. Harris and J. M. White, Chem. Commun., 2020, 56, 3313 DOI: 10.1039/C9CC09896H

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