Restricted Rotation and NOE Transfer: A Conformational Study of Some Substituted (9-Anthryl)carbinol Derivatives

Innocenzo de Riggi; Albert Virgili; Maria de Moragas; Carlos Jaime

doi:10.1021/jo00106a010

Restricted Rotation and NOE Transfer: A Conformational Study of Some Substituted (9-Anthryl)carbinol Derivatives

Innocenzo de Riggi, Albert Virgili, Maria de Moragas, Carlos Jaime

Department of Chemistry

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Abstract

Four alkyl- and aryl(9-anthryl)carbinols (methyl, isopropyl, tert-butyl, and phenyl) were synthesized and revealed restricted rotation about the C9–C11 bond. Their free energy of activation for rotation has been determined, being 11.0, 14.0, 21.7, and 9.8 kcal/mol, respectively. The application of NOE enhancement and relaxation time measurements for the determination of the activation energy for bond rotation is described. The good agreement with the values obtained with the coalescence temperature method bears out that the NOE based approach is a good alternative for the determination of high rotational barriers. Molecular Mechanics (MM2) calculations give values close to the experimental ones. © 1995, American Chemical Society. All rights reserved.

Original language	English
Pages (from-to)	27-31
Journal	Journal of Organic Chemistry
Volume	60
Issue number	1
DOIs	https://doi.org/10.1021/jo00106a010
Publication status	Published - 1 Jan 1995

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title = "Restricted Rotation and NOE Transfer: A Conformational Study of Some Substituted (9-Anthryl)carbinol Derivatives",

abstract = "Four alkyl- and aryl(9-anthryl)carbinols (methyl, isopropyl, tert-butyl, and phenyl) were synthesized and revealed restricted rotation about the C9–C11 bond. Their free energy of activation for rotation has been determined, being 11.0, 14.0, 21.7, and 9.8 kcal/mol, respectively. The application of NOE enhancement and relaxation time measurements for the determination of the activation energy for bond rotation is described. The good agreement with the values obtained with the coalescence temperature method bears out that the NOE based approach is a good alternative for the determination of high rotational barriers. Molecular Mechanics (MM2) calculations give values close to the experimental ones. {\textcopyright} 1995, American Chemical Society. All rights reserved.",

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T1 - Restricted Rotation and NOE Transfer: A Conformational Study of Some Substituted (9-Anthryl)carbinol Derivatives

AU - de Riggi, Innocenzo

AU - Virgili, Albert

AU - de Moragas, Maria

AU - Jaime, Carlos

PY - 1995/1/1

Y1 - 1995/1/1

N2 - Four alkyl- and aryl(9-anthryl)carbinols (methyl, isopropyl, tert-butyl, and phenyl) were synthesized and revealed restricted rotation about the C9–C11 bond. Their free energy of activation for rotation has been determined, being 11.0, 14.0, 21.7, and 9.8 kcal/mol, respectively. The application of NOE enhancement and relaxation time measurements for the determination of the activation energy for bond rotation is described. The good agreement with the values obtained with the coalescence temperature method bears out that the NOE based approach is a good alternative for the determination of high rotational barriers. Molecular Mechanics (MM2) calculations give values close to the experimental ones. © 1995, American Chemical Society. All rights reserved.

AB - Four alkyl- and aryl(9-anthryl)carbinols (methyl, isopropyl, tert-butyl, and phenyl) were synthesized and revealed restricted rotation about the C9–C11 bond. Their free energy of activation for rotation has been determined, being 11.0, 14.0, 21.7, and 9.8 kcal/mol, respectively. The application of NOE enhancement and relaxation time measurements for the determination of the activation energy for bond rotation is described. The good agreement with the values obtained with the coalescence temperature method bears out that the NOE based approach is a good alternative for the determination of high rotational barriers. Molecular Mechanics (MM2) calculations give values close to the experimental ones. © 1995, American Chemical Society. All rights reserved.

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DO - 10.1021/jo00106a010

M3 - Article

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VL - 60

SP - 27

EP - 31

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

Restricted Rotation and NOE Transfer: A Conformational Study of Some Substituted (9-Anthryl)carbinol Derivatives

Abstract

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