Ring inversion barrier of diazepam and derivatives: An ab initio study

Béla Paizs, Miklós Simonyi

Research output: Contribution to journalArticle

25 Citations (Scopus)


Systematic ab initio calculations were performed to investigate the ring inversion process of various 1,4-diazepines including diazepam, N1- desmethyldiazepam, and 3-methyl-N1-desmethyldiazepam. The diazepine ring adopts a shape of a boat; owing to asymmetric substitution two such boats are possible in mirror image relation to each other. In the present study both structural and solvent effects were investigated on the energetics of ring inversion of nine diazepine derivatives. The calculated ring inversion barriers for diazepam (17.6 kcal/mol) and N1-desmethyldiazepam (10.9 kcal/mol) are in good agreement with the corresponding experimental data. In the cases of diazepam and N1-desmethyldiazepam, the calculated minimum energy path of the ring inversion is asymmetric contrary to the fact that the terminals (M and P conformers) are equienergetic.

Original languageEnglish
Pages (from-to)651-658
Number of pages8
Issue number8
Publication statusPublished - Oct 1 1999


  • Chirality
  • Density functional
  • Diazepine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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