Computational Studies on the Reactivity of Substituted 1,2-Dihydro-1,2-azaborines

• Tipo: Artigo em Revista Científica Internacional
• Data: 2009

Autores

Pedro J Silva (Autor) Outra; Maria Joao Ramos (Autor) FCUP

Revista

Título: Journal of Organic Chemistry

Vol. 74

Páginas: 6120-6129

ISSN: 0022-3263

Editora: American Chemical Society

Indexação

ISI Web of Knowledge - 13 Citações

Scopus - 15 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: P-003-GPJ

DOI: 10.1021/jo900980d

Abstract (EN): We have investigated important intermediates of electrophilic aromatic substitution reactions and one-electron oxidation of substituted 1,2-dihydro-1,2-azaborines with density-functional theory. The results show that electrophilic substitution reactions and one-electron oxidation of substituted 1,2-azaborines are generally much more favorable than those of the corresponding benzene derivatives. Both chlorination and nitration of several boron-unsubstituted 1,2-azaborines are expected to break the boron-hydrogen bond, yielding boron-chlorinated 1,2-azaborines and a novel class of boron-bound 1,2-azaborinyl nitrites, respectively. Comparison between the relative stabilities of C(3)-bound and C(5)-bound Wheland intermediates of different electrophilic substitution reactions of 1,2-azaborines further suggests that the preference of the C(3)- over C(5)-substitution decreases with decreasing electrophilicity of the attacking group.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 10