Issue 94, 2016

Experimental and theoretical study of intramolecular O⋯O interaction in structurally rigid β-keto carboxylic esters

Abstract

Here we report the crystal structures of quinolone carboxylate and bisethoxycarbonylvinylaniline derivates containing an O⋯O distance shorter than the sum of their van der Waals radii, which can be ascribed to their steric demand per se, which provide unequivocal evidence of intramolecular 1,5-closed shell type interaction. Theoretical studies including Quantum Theory of Atoms in Molecules (QTAIM) and Natural Bond Orbital (NBO) analysis are employed to characterize the nature of the closed shell O⋯O interaction. We found that the lone pair electrons on the interacting oxygens undergo stabilization due to negative hyperconjugation and maintains the otherwise repulsive O⋯O close contact.

Graphical abstract: Experimental and theoretical study of intramolecular O⋯O interaction in structurally rigid β-keto carboxylic esters

Supplementary files

Article information

Article type
Communication
Submitted
14 Aug 2016
Accepted
18 Sep 2016
First published
19 Sep 2016

RSC Adv., 2016,6, 91689-91693

Experimental and theoretical study of intramolecular O⋯O interaction in structurally rigid β-keto carboxylic esters

C. Sharma, A. K. Singh, J. Joy, E. D. Jemmis and S. K. Awasthi, RSC Adv., 2016, 6, 91689 DOI: 10.1039/C6RA20483J

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