Document Detail


Ring inversion barrier of diazepam and derivatives: An ab initio study.
MedLine Citation:
PMID:  10467317     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Systematic ab initio calculations were performed to investigate the ring inversion process of various 1,4-diazepines including diazepam, N(1)-desmethyldiazepam, and 3-methyl-N(1)-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 N(1)-desmethyldiazepam (10.9 kcal/mol) are in good agreement with the corresponding experimental data. In the cases of diazepam and N(1)-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.
Authors:
B Paizs; M Simonyi
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chirality     Volume:  11     ISSN:  0899-0042     ISO Abbreviation:  Chirality     Publication Date:  1999  
Date Detail:
Created Date:  1999-10-25     Completed Date:  1999-10-25     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8914261     Medline TA:  Chirality     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  651-8     Citation Subset:  IM    
Copyright Information:
Copyright 1999 Wiley-Liss, Inc.
Affiliation:
Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, P.O. Box 17, 1525 Budapest, Hungary. B.Paizs@DKFZ-Heidelberg.de
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MeSH Terms
Descriptor/Qualifier:
Diazepam / analogs & derivatives,  chemistry*
Molecular Conformation
Chemical
Reg. No./Substance:
439-14-5/Diazepam

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