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

doi:10.1021/jo00371a007

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-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 language	English
Pages (from-to)	3951-3955
Journal	Journal of Organic Chemistry
Volume	51
Issue number	21
DOIs	https://doi.org/10.1021/jo00371a007
Publication status	Published - 1 Jan 1986

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title = "Molecular Mechanics Calculations on the Csp3-Csp2 Rotation in the N,3,3-Trimethyl-2-phenyl-4-piperidone System",

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. {\textcopyright} 1986, American Chemical Society. All rights reserved.",

author = "Carlos Jaime and Mario Rubiralta and Miguel Feliz and Ernest Giralt",

year = "1986",

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language = "English",

volume = "51",

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journal = "Journal of Organic Chemistry",

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AU - Feliz, Miguel

AU - Giralt, Ernest

PY - 1986/1/1

Y1 - 1986/1/1

N2 - 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.

AB - 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.

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DO - 10.1021/jo00371a007

M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

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

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