Racemization Barriers of 1,1‘-Binaphthyl and 1,1‘-Binaphthalene-2,2‘-diol: A DFT Study
2003; American Chemical Society; Volume: 68; Issue: 14 Linguagem: Inglês
10.1021/jo034344u
ISSN1520-6904
AutoresL. Meca, David Řeha, Zdeněk Havlas,
Tópico(s)Chemical Reaction Mechanisms
ResumoDensity 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.
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