Quantitation of Long-range Effects in Steroids by Molecular Orbital Calculations

Peter A. Kollman; Manfred E. Wolff; Donald D. Giannini; William L. Duax; Stephen Rothenberg

doi:10.1021/ja00790a022

Quantitation of Long-range Effects in Steroids by Molecular Orbital Calculations

Peter A. Kollman
, Manfred E. Wolff
, Donald D. Giannini
, William L. Duax
, Stephen Rothenberg

Department of Structural Biology

University of California at San Francisco
Information Systems Design

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

43 Scopus citations

Abstract

The calculation of electron densities in portions of cortisol (1), 6α-fluorocortisol (9), and 9α-fluorocortisol (2) using X-ray structures and the CNDO/2 method is described. It is shown that the long-range influence of a substituent group on another portion of the steroid has two components: conformational steric transmission (CST) and conformational electronic transmission (CET). The implications of this for biological activity of 1, 2, and 9 are discussed. The effects of electronegative and electropositive substitution on the H-bonding ability of ethanol (both as proton donor and acceptor) are examined by the CNDO/2 molecular orbital method and the results are related to the steroid hydroxyl electron densities.

Original language	English
Pages (from-to)	2869-2873
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	95
Issue number	9
DOIs	https://doi.org/10.1021/ja00790a022
State	Published - May 1 1973

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title = "Quantitation of Long-range Effects in Steroids by Molecular Orbital Calculations",

abstract = "The calculation of electron densities in portions of cortisol (1), 6α-fluorocortisol (9), and 9α-fluorocortisol (2) using X-ray structures and the CNDO/2 method is described. It is shown that the long-range influence of a substituent group on another portion of the steroid has two components: conformational steric transmission (CST) and conformational electronic transmission (CET). The implications of this for biological activity of 1, 2, and 9 are discussed. The effects of electronegative and electropositive substitution on the H-bonding ability of ethanol (both as proton donor and acceptor) are examined by the CNDO/2 molecular orbital method and the results are related to the steroid hydroxyl electron densities.",

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year = "1973",

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T1 - Quantitation of Long-range Effects in Steroids by Molecular Orbital Calculations

AU - Kollman, Peter A.

AU - Wolff, Manfred E.

AU - Giannini, Donald D.

AU - Duax, William L.

AU - Rothenberg, Stephen

PY - 1973/5/1

Y1 - 1973/5/1

N2 - The calculation of electron densities in portions of cortisol (1), 6α-fluorocortisol (9), and 9α-fluorocortisol (2) using X-ray structures and the CNDO/2 method is described. It is shown that the long-range influence of a substituent group on another portion of the steroid has two components: conformational steric transmission (CST) and conformational electronic transmission (CET). The implications of this for biological activity of 1, 2, and 9 are discussed. The effects of electronegative and electropositive substitution on the H-bonding ability of ethanol (both as proton donor and acceptor) are examined by the CNDO/2 molecular orbital method and the results are related to the steroid hydroxyl electron densities.

AB - The calculation of electron densities in portions of cortisol (1), 6α-fluorocortisol (9), and 9α-fluorocortisol (2) using X-ray structures and the CNDO/2 method is described. It is shown that the long-range influence of a substituent group on another portion of the steroid has two components: conformational steric transmission (CST) and conformational electronic transmission (CET). The implications of this for biological activity of 1, 2, and 9 are discussed. The effects of electronegative and electropositive substitution on the H-bonding ability of ethanol (both as proton donor and acceptor) are examined by the CNDO/2 molecular orbital method and the results are related to the steroid hydroxyl electron densities.

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AN - SCOPUS:0015912226

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SP - 2869

EP - 2873

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 9

ER -

Quantitation of Long-range Effects in Steroids by Molecular Orbital Calculations

Abstract

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