Conformational preferences of α-functionalised keten-S,N-acetals: Potential role of SO and SS interactions in solution
Data(s) |
30/01/1995
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Resumo |
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. |
Formato |
application/pdf |
Identificador |
http://eprints.iisc.ernet.in/37430/1/Conformational.pdf 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. |
Publicador |
Elsevier Science |
Relação |
http://dx.doi.org/10.1016/0040-4020(94)01023-S http://eprints.iisc.ernet.in/37430/ |
Palavras-Chave | #Organic Chemistry |
Tipo |
Journal Article PeerReviewed |