title: Boron-substituted 1,3-dihydro-1,3-azaborines: synthesis, structure, and evaluation of aromaticity.
abstract: Getting the family together: A general synthetic strategy based on nucleophilic substitution provided B-substituted 1,3-dihydro-1,3-azaborines (see scheme), BN isosteres of arenes with potential for application in biomedicine and materials science. Experimental structural analysis and calculations suggest that the aromaticity of the 1,3-dihydro-1,3-azaborine heterocycle is intermediate between that of benzene and that of 1,2-dihydro-1,2-azaborine.
authors.affiliation: Department of Chemistry and Biochemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.
authors.forename: Senmiao
authors.initials: S
authors.lastname: Xu
authors.forename: Tanya C
authors.initials: TC
authors.lastname: Mikulas
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.forename: David A
authors.initials: DA
authors.lastname: Dixon
authors.forename: Shih-Yuan
authors.initials: SY
authors.lastname: Liu
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation
chemical_list: D001372:Aza Compounds; D001896:Boron Compounds; D001554:Benzene
keywords: aromaticity; azaborines; boron; heterocycles; synthetic methods