Synthesis and characterization of new (N→B) phenyl substituted[N-benzyliminodiacetate O,O′,N]boranes

The synthesis of nine (N→B) phenyl substituted[N-benzyliminodiacetate-O,O’,N]boranes 3a-3i is reported herein. These compounds were characterized by 1H, 13C, 11B, HETCOR, NOESY, infrared spectroscopy, mass spectrometry and in the case of compounds 3d and 3g also by 19F NMR. All compounds exhibit a b...

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Bibliographic Details
Authors: HIRAM ISAAC BELTRAN CONDE, ROSA LUISA SANTILLAN BACA
Format: article
Status:Published version
Publication Date:2005
Country:México
Institution:Universidad Autónoma Metropolitana
Repository:Concentración de Recursos de Información Científica y Académica, UAM Cuajimalpa
Language:English
OAI Identifier:oai:ilitia.cua.uam.mx:123456789/49
Online Access:http://ilitia.cua.uam.mx:8080/jspui/handle/123456789/49
Access Level:Open access
Keyword:info:eu-repo/classification/cti/2
Boranos
Ácido Iminodiacético
RMN
Ariloboranos y σ Hammett
Description
Summary:The synthesis of nine (N→B) phenyl substituted[N-benzyliminodiacetate-O,O’,N]boranes 3a-3i is reported herein. These compounds were characterized by 1H, 13C, 11B, HETCOR, NOESY, infrared spectroscopy, mass spectrometry and in the case of compounds 3d and 3g also by 19F NMR. All compounds exhibit a bicyclic structure due to the presence of an intramolecular N→B coordination bond. The structure of 4-chlorophenyl [N benzyliminodiacetate-O,O’,N]borane 3e was further established by a single crystal x-ray diffraction study. The correlation between δ(11B) of compounds 3a, 3d-3i and σHammett values shows that the strength of the N→B bond depends on the electronic factors of the substituent on the B-phenyl group.