Substituted γ-Lactones with Vicinal Hydrogen Atoms. Conformational Study by MM2 Calculations and Coupling Constant Analysis

Carlos Jaime; Cristóbal Segura; Immaculada Dinarés; Josep Font

doi:10.1021/jo00053a029

Substituted γ-Lactones with Vicinal Hydrogen Atoms. Conformational Study by MM₂ Calculations and Coupling Constant Analysis

Carlos Jaime, Cristóbal Segura, Immaculada Dinarés, Josep Font

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

27 Citations (Scopus)

Abstract

The conformational analysis of substituted γ-lactones with vicinal hydrogen atoms is carried out by the MM2/3JHH tandem. The agreement between experimentally available and calculated data is globally correct (rms = 1.16 Hz). A general preference for a hydroxyl group to occupy the equatorial position if it is on C-2 or the axial position if it is on C-3 or C-4 is observed as a consequence of the presence of H bond or of the gauche effect, respectively. © 1993, American Chemical Society. All rights reserved.

Original language	English
Pages (from-to)	154-158
Journal	Journal of Organic Chemistry
Volume	58
Issue number	1
DOIs	https://doi.org/10.1021/jo00053a029
Publication status	Published - 1 Jan 1993

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10.1021/jo00053a029

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title = "Substituted γ-Lactones with Vicinal Hydrogen Atoms. Conformational Study by MM2 Calculations and Coupling Constant Analysis",

abstract = "The conformational analysis of substituted γ-lactones with vicinal hydrogen atoms is carried out by the MM2/3JHH tandem. The agreement between experimentally available and calculated data is globally correct (rms = 1.16 Hz). A general preference for a hydroxyl group to occupy the equatorial position if it is on C-2 or the axial position if it is on C-3 or C-4 is observed as a consequence of the presence of H bond or of the gauche effect, respectively. {\textcopyright} 1993, American Chemical Society. All rights reserved.",

author = "Carlos Jaime and Crist{\'o}bal Segura and Immaculada Dinar{\'e}s and Josep Font",

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AU - Jaime, Carlos

AU - Segura, Cristóbal

AU - Dinarés, Immaculada

AU - Font, Josep

PY - 1993/1/1

Y1 - 1993/1/1

N2 - The conformational analysis of substituted γ-lactones with vicinal hydrogen atoms is carried out by the MM2/3JHH tandem. The agreement between experimentally available and calculated data is globally correct (rms = 1.16 Hz). A general preference for a hydroxyl group to occupy the equatorial position if it is on C-2 or the axial position if it is on C-3 or C-4 is observed as a consequence of the presence of H bond or of the gauche effect, respectively. © 1993, American Chemical Society. All rights reserved.

AB - The conformational analysis of substituted γ-lactones with vicinal hydrogen atoms is carried out by the MM2/3JHH tandem. The agreement between experimentally available and calculated data is globally correct (rms = 1.16 Hz). A general preference for a hydroxyl group to occupy the equatorial position if it is on C-2 or the axial position if it is on C-3 or C-4 is observed as a consequence of the presence of H bond or of the gauche effect, respectively. © 1993, American Chemical Society. All rights reserved.

U2 - 10.1021/jo00053a029

DO - 10.1021/jo00053a029

M3 - Article

SN - 0022-3263

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EP - 158

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

Substituted γ-Lactones with Vicinal Hydrogen Atoms. Conformational Study by MM2 Calculations and Coupling Constant Analysis

Abstract

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Substituted γ-Lactones with Vicinal Hydrogen Atoms. Conformational Study by MM₂ Calculations and Coupling Constant Analysis