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

Research output: Contribution to journalArticleOther

Abstract

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
Volume3
Issue number2 SPEC. ISS.
Publication statusPublished - 1988
Externally publishedYes

Cite this

Winkler, D. A., Liepa, A. J., Willing, R. I., Anderson McKay, J. E., Winzenberg, K. N., & Morton, T. C. (1988). NMR and molecular orbital studies of isomerism and tautomerism in oximes of 2-acyl cyclic 1,3-diones. Drug design and delivery, 3(2 SPEC. ISS.), 171-183.
Winkler, D. A. ; Liepa, A. J. ; Willing, R. I. ; Anderson McKay, J. E. ; Winzenberg, K. N. ; Morton, T. C. / NMR and molecular orbital studies of isomerism and tautomerism in oximes of 2-acyl cyclic 1,3-diones. In: Drug design and delivery. 1988 ; Vol. 3, No. 2 SPEC. ISS. pp. 171-183.
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abstract = "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.",
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Winkler, DA, Liepa, AJ, Willing, RI, Anderson McKay, JE, Winzenberg, KN & Morton, TC 1988, 'NMR and molecular orbital studies of isomerism and tautomerism in oximes of 2-acyl cyclic 1,3-diones' Drug design and delivery, vol. 3, no. 2 SPEC. ISS., pp. 171-183.

NMR and molecular orbital studies of isomerism and tautomerism in oximes of 2-acyl cyclic 1,3-diones. / Winkler, D. A.; Liepa, A. J.; Willing, R. I.; Anderson McKay, J. E.; Winzenberg, K. N.; Morton, T. C.

In: Drug design and delivery, Vol. 3, No. 2 SPEC. ISS., 1988, p. 171-183.

Research output: Contribution to journalArticleOther

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T1 - NMR and molecular orbital studies of isomerism and tautomerism in oximes of 2-acyl cyclic 1,3-diones

AU - Winkler, D. A.

AU - Liepa, A. J.

AU - Willing, R. I.

AU - Anderson McKay, J. E.

AU - Winzenberg, K. N.

AU - Morton, T. C.

PY - 1988

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AB - 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.

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Winkler DA, Liepa AJ, Willing RI, Anderson McKay JE, Winzenberg KN, Morton TC. NMR and molecular orbital studies of isomerism and tautomerism in oximes of 2-acyl cyclic 1,3-diones. Drug design and delivery. 1988;3(2 SPEC. ISS.):171-183.