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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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|
|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|
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