Optical Rotatory Dispersion Studies. C.<sup>1</sup> Variable-Temperature Circular Dichroism Studies of Ring-Conformational and Rotational Equilibria in Cyclohexanones<sup>2</sup>

Wellman, Keith M.; Briggs, W.Scott; Djerassi, Carl

doi:10.1021/ja01079a014

Cited by 40 publications

(11 citation statements)

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“…Roberts et al [5], for example, pointed out that the experimental structure of cortisol determined from direct methods did not agree with Kier's calculations. Their experimental data confirmed earlier experiment of Wellman et al [6]. The experimental torsion q5 angle [7], C(16) -C(17) -C(20) -0(20) of corticosterone is -13.56".…”

Section: Introductionsupporting

confidence: 86%

PCILO study of the conformation of 20‐oxopregnane hormones

Viana

Takahata

1982

Int J of Quantum Chemistry

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PCILO calculations on conformations of the C-17 side chains of three 20-oxopregnane hormones, progesterone, corticosterone, and cortisol, reveal that the calculated conformations are generally in close agreement with those observed crystallographically. Average deviation of the calculated rotation angle around the C(17)-C(20) bond from the experiment is 9". The PCILO calculations also predict the intramolecular hydrogen bond between the 20-carbonyl group and the 21-hydroxyl for the three hormones. This is in accordance with experiment. It was concluded that the PCILO method is reliable in predicting conformations of the side chains of hormones whereas the extended Huckel theory (EHT) predicted wrong conformations. Based upon the PCILO calculations, biological activities of the hormones are discussed.

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Section: Introductionsupporting

confidence: 86%

PCILO study of the conformation of 20‐oxopregnane hormones

Viana

Takahata

1982

Int J of Quantum Chemistry

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“…3(b)]. This orientation is in agreement with solution spectral measurements (Wellman & Djerassi, 1965).…”

supporting

confidence: 89%

9α-Methoxycortisol

Weeks¹,

Duax²,

Wolff³

1976

Acta Crystallogr Sect B

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“…Inspection of the torsional angles involving the C(17) side chain shows that it has the usual corticoid orientation (Weeks, Duax & Wolff, 1973). Atoms 0(20) and O(21) are cis eoplanar, and 0 (20) is oriented over the D-ring in agreement with solution spectral measurements (Wellman & Djerassi, 1965).…”

supporting

confidence: 71%