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Experimental and theoretical study of intramolecular O center dot center dot center dot O interaction in structurally rigid beta-keto carboxylic esters

Sharma, Chiranjeev and Singh, Ashawani K and Joy, Jyothish and Jemmis, Eluvathingal D and Awasthi, Satish Kumar (2016) Experimental and theoretical study of intramolecular O center dot center dot center dot O interaction in structurally rigid beta-keto carboxylic esters. In: RSC ADVANCES, 6 (94). pp. 91689-91693.

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Official URL: http://dx.doi.org/10.1039/c6ra20483j

Abstract

Here we report the crystal structures of quinolone carboxylate and bisethoxycarbonylvinylaniline derivates containing an O center dot center dot center dot 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 center dot center dot center dot 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 center dot center dot center dot O close contact.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the ROYAL SOC CHEMISTRY, THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 03 Dec 2016 09:57
Last Modified: 26 Feb 2019 08:48
URI: http://eprints.iisc.ac.in/id/eprint/55382

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