Racemization Barriers of 1,1‘-Binaphthyl and 1,1‘-Binaphthalene-2,2‘-diol:  A DFT Study

Density functional theory has been applied to the study of various pathways and transition states for the configurational inversion of 1,1‘-binaphthyl (1) and 1,1‘-binaphthalene-2,2‘-diol (2). The preferred pathway is found to be anti with centrosymmetric transition state. Whereas the reaction path...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 68; no. 14; pp. 5677 - 5680
Main Authors Meca, Luděk, Řeha, David, Havlas, Zdeněk
Format Journal Article
LanguageEnglish
Published Washington, DC American Chemical Society 11.07.2003
Subjects
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
Diol
Bond length
Transition state
Bicyclic compound
Theoretical study
Density functional method
Racemization
Naphthalene derivatives
Energy barrier
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Summary:Density functional theory has been applied to the study of various pathways and transition states for the configurational inversion of 1,1‘-binaphthyl (1) and 1,1‘-binaphthalene-2,2‘-diol (2). The preferred pathway is found to be anti with centrosymmetric transition state. Whereas the reaction path of 1 goes downhill from transition to ground state, in the case of 2 it contains one unexpected local minimum. Very satisfactory agreement with available experimental values of activation Gibbs energies is achieved.
Bibliography:ark:/67375/TPS-4SWGKFZL-8
istex:071ACB05BB2E17DAB0B7FCC889D79638B87B28D9
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034344u