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Synthetic and computational investigation of neighboring group participation by a nucleophilic disulfide bond.
Yamamoto, Takuhei; Fukuta, Koki; Kariya, Yuki; Matsuura, Taiki; Hagiwara, Hiroaki; Uno, Bunji; Esaka, Yukihiro.
Afiliação
  • Yamamoto T; Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
  • Fukuta K; United Graduate School of Drug Discovery and Medical Information Science, Gifu University, 1-1 Yanaido, Gifu 501-1194, Japan.
  • Kariya Y; Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
  • Matsuura T; Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
  • Hagiwara H; Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
  • Uno B; Department of Chemistry, Faculty of Education, Gifu University, 1-1 Yanaido, Gifu 501-1193, Japan.
  • Esaka Y; Faculty of Pharmacy, Gifu University of Medical Science, 4-3-3 Nijigaoka, Kani, Gifu 509-0923, Japan.
Org Biomol Chem ; 21(1): 65-68, 2022 12 21.
Article em En | MEDLINE | ID: mdl-36445233
ABSTRACT
Disulfide bonds of 2-isocyanatophenyl methyl disulfide and 2-endo-isocyanato-6-endo-(methyldisulfanyl)bicyclo[2.2.1]heptane showed neighboring group participation in the formation of thiocarbamates. Natural Bond Orbital (NBO) analyses revealed that the unusual nucleophilicity requires a rigid through-space interaction between a lone pair of the disulfide bond and an antibonding orbital of isocyanate.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2022 Tipo de documento: Article
Texto completo
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2022 Tipo de documento: Article