Molecular Mechanics Calculations on the C<inf>sp</inf>3-C<inf>sp</inf>2 Rotation in the N,3,3-Trimethyl-2-phenyl-4-piperidone System

Carlos Jaime, Mario Rubiralta, Miguel Feliz, Ernest Giralt

Research output: Contribution to journalArticleResearchpeer-review

5 Citations (Scopus)

Abstract

The rotational pathway of the phenyl ring in N, 3,3-trimethyl-2-phenyl-4-piperidone has been determined by molecular mechanics calculations to be chair piperidone ⇋ twist-boat piperidone ⇋ phenyl rotation. The calculated barrier height for the process (ca. 63 kJ/mol) is in good agreement with the previously reported experimental value of 54 kJ/mol in a remotely substituted phenyl derivative determined by 1H DNMR. © 1986, American Chemical Society. All rights reserved.
Original languageEnglish
Pages (from-to)3951-3955
JournalJournal of Organic Chemistry
Volume51
Issue number21
DOIs
Publication statusPublished - 1 Jan 1986

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