Unexpected reactivity difference between iodo-alkene moieties of steroids possessing remote lactame or cycloalkane structural units: A theoretical approach

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Abstract

The steroidal ring A possessing cyclohexane vs. δ-valerolactame structures shows a 'long-range effect' on the reactivity of the 'iodovinyl' functionality of the ring D. The strikingly different reactivity of 17-iodo-16-ene functionality of steroids is explained on the basis of the redistribution of kinetic energy of the system. The vibrational energy localized on the 'iodovinyl' moiety proved to be determinant in the CI bond-breaking process. The appearance of the lactame moiety in the ring A supports a redistribution of the kinetic energy on the molecule. As a result, a drastic decrease in C-I bond stretching has been obtained, which could diminish the C-I bond breaking, and therefore, results in decreased reactivity of the iodovinyl moiety in agreement with experimental findings.

Original languageEnglish
Pages (from-to)69-75
Number of pages7
JournalJournal of biochemical and biophysical methods
Volume61
Issue number1-2 SPEC. ISS.
DOIs
Publication statusPublished - Oct 29 2004

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Keywords

  • Long-range effect
  • Reactivity
  • Steroid

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry

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