Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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On the Nitrogen Inversion of Isoxazolidin-5-ones
Hidetoshi NodaMasakatsu Shibasaki
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2019 Volume 67 Issue 11 Pages 1248-1249

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Abstract

The nitrogen inversion energies of a series of N-substituted isoxazolidin-5-ones were studied by density functional theory. The transition state energy was found to strongly correlate with the s-character of the lone pair of electrons on the nitrogen in the ground state. Although the activation energy trends for isxazolidin-5-ones and isoxazolidines are similar, their conformational equilibria are slightly different and the isoxazolidin-5-one inversion energies are generally higher.

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© 2019 The Pharmaceutical Society of Japan
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