NMR and molecular orbital studies of isomerism and tautomerism in oximes of 2-acyl cyclic 1,3-diones

D. A. Winkler, A. J. Liepa, R. I. Willing, J. E. Anderson McKay, K. N. Winzenberg, T. C. Morton

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2 Citations (Scopus)


Molecular orbital calculations and 13C and 15N NMR experiments have been performed on the O-methyl oximes of two types of 2-acyl cyclic 1,3-diones. One (III; X = CH2) was based on cyclohexane, and the other (X = O) on pyran. The data indicate that both the cyclohexane and pyran compounds prefer to exist as the oxine, rather than the enamine isomer. Two equivalent, interconverting, keto-enol tautomers exist in the cyclohexane compound. The pyran compound exists as the lactone-enol tautomer. Our results have implications in the design of herbicidal compounds and drugs containing similar tautomeric systems.

Original languageEnglish
Pages (from-to)171-183
Number of pages13
JournalDrug Design and Delivery
Issue number2 SPEC. ISS.
Publication statusPublished - 1988
Externally publishedYes

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