Conformational preferences of α-functionalised keten-S,N-acetals: Potential role of SO and SS interactions in solution

Dixit, Arun N and Reddy, Venodhar K and Deshmukh, Abdul Rakeeb AS and Rajappa, Srinivasachari and Ganguly, Bishwajit and Chandrasekhar, Jayaraman (1995) Conformational preferences of α-functionalised keten-S,N-acetals: Potential role of SO and SS interactions in solution. In: Tetrahedron, 51 (5). pp. 1437-1448.

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Abstract

PMR spectra of carbonyl compounds 2a-k reveal significant variations in the population of E and Z isomers on changing the solvent from CDCl3 to DMSO-d6. In non-polar media, the intramolecular N-H…. O hydrogen bonded form is exclusively observed. In DMSO-d6, the alternative Z form is also populated. A similar conformational switch is also noted in the corresponding thiones. Different interpretations are critically analysed. The most consistent explanation is suggested to involvean interplay of N-H….X hydrogen bonding and S…X attractive interaction (X = O,S) in these systems. Ab initio calculations support this interpretation.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier Science
Additional Information:	Copyright of this article belongs to Elsevier Science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	15 Jun 2011 09:13
Last Modified:	15 Jun 2011 09:13
URI:	http://eprints.iisc.ac.in/id/eprint/37430

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