Stabilities for the eight isomeric forms of the steroid skeleton (perhydrocyclopentanophenanthrene)

K. Tantuco, E. Deretey, I. Csizmadia

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The relative stabilities for the eight isomers of the steroid skeleton resulting from three ring fusions (A/B, B/C, C/D) were determined using molecular mechanics (MM+), semi-empirical (AM1 and PM3), and ab initio HF/3- 21G molecular orbital calculations. Five of the isomers studied, (trans, trans, trans), (cis, trans, trans), (trans, trans, cis), (trans, cis, trans), and (cis, trans, cis) occur naturally. The calculated relative energies for the three methods gave conflicting results. The ab initio order of stability was the following: (trans, trans, trans) > (trans, trans, cis) > (trans, cis, trans) > (cis, trans, trans) > (trans, cis, cis) > (cis, trans, cis) > (cis, cis, trans)> (cis, cis, cis). (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)97-111
Number of pages15
JournalJournal of Molecular Structure: THEOCHEM
Volume503
Issue number1-2
DOIs
Publication statusPublished - May 9 2000

Fingerprint

steroids
Mechanics
musculoskeletal system
Skeleton
Isomers
isomers
Steroids
Orbital calculations
Molecular mechanics
Molecular orbitals
molecular orbitals
Fusion reactions
fusion
rings
energy

Keywords

  • Ab initio stabilities
  • Cholesterol
  • Cholic acid
  • Geometrical isomers of steroids
  • Perhydrocyclopentanophenanthre

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Stabilities for the eight isomeric forms of the steroid skeleton (perhydrocyclopentanophenanthrene). / Tantuco, K.; Deretey, E.; Csizmadia, I.

In: Journal of Molecular Structure: THEOCHEM, Vol. 503, No. 1-2, 09.05.2000, p. 97-111.

Research output: Contribution to journalArticle

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