title: Synthesis and structural investigation of internally coordinated alpha-amidoboronic acids.
abstract: [structure: see text] Six new N-acyl-boroGly derivatives, along with their N-acyl-boroSar analogues, have been synthesized by modification of conventional procedures. Structural characterization of these alpha-amidoboronic acids was accomplished by extensive use of 11B and 1H NMR spectroscopy. These compounds were prepared to determine the extent of intramolecular B-O dative bond formation within the context of a five-membered (:O=C-N-C-B) ring motif. It is shown that the formation of such dative bonds depends on the nature of the substituents at both the acyl carbon and the nitrogen atoms. Computational evidence from second-order Møller-Plesset perturbation theory is provided in support of these findings.
authors.affiliation: Department of Biochemistry, Tufts University School of Medicine, 136 Harrison Avenue, Boston, Massachusetts 02111, USA.
authors.forename: Jack H
authors.initials: JH
authors.lastname: Lai
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Liu
authors.forename: Wengen
authors.initials: W
authors.lastname: Wu
authors.forename: Yuhong
authors.initials: Y
authors.lastname: Zhou
authors.forename: Hlaing H
authors.initials: HH
authors.lastname: Maw
authors.forename: William W
authors.initials: WW
authors.lastname: Bachovchin
authors.forename: Krishna L
authors.initials: KL
authors.lastname: Bhat
authors.forename: Charles W
authors.initials: CW
authors.lastname: Bock
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D000577:Amides; D001897:Boronic Acids