Synthesis and characterization of boronates derived from non-symmetric amino-bis-phenols

被引:22
作者
Abreu, A
Alas, SJ
Beltrán, HI
Santillan, R
Farfán, N
机构
[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico
[2] Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Mexico City 04510, DF, Mexico
关键词
boron; boronate; tridentate ligand; X-ray crystallography; NMR; supramolecular arrangement;
D O I
10.1016/j.jorganchem.2005.08.042
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The condensation of 2-[[(2-hydroxyphenyl) amino]methyl]-phenols (1a-1e) with different arylboronic acids led to 12 new monomeric boronates of the type 2-aryl-dibenzo[d,h]-6-aza-1,3-dioxa-2-boracyclononene (2a-21). The boronates were characterized by H-1-, C-13-, B-11- and 2D-NMR experiments, FT infrared, mass spectra and elemental analyses. The stereochemistry of the H-N -> B-Ph fusion is always cis, as established through the NMR spectra, as well as the X-ray structures of four boronates (2a, 2e, 2f and 21). Hydrogen bonds between the amine proton and the oxygen ester of the five- membered ring are present in three X-ray structures (2a, 2e and 2f), while the supramolecular structure in the derivative possessing a primary amine (21) is built up through the protons present in this moiety instead of the proton from the H-N -> B-Ph fragment. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:337 / 348
页数:12
相关论文
共 43 条
[1]   SMALL MOLECULE ANALOGS FOR THE SPECIFIC IRON-BINDING SITE OF LACTOFERRIN - A SINGLE-CRYSTAL X-RAY STRUCTURE OF BIS(METHANOL)BIS[2-(5-METHYLPYRAZOL-3-YL)PHENOLATO]IRON(III) NITRATE-METHANOL AND SPECTROSCOPIC STUDIES ON IRON(III) PHENOLATE COMPLEXES [J].
AINSCOUGH, EW ;
BRODIE, AM ;
PLOWMAN, JE ;
BROWN, KL ;
ADDISON, AW ;
GAINSFORD, AR .
INORGANIC CHEMISTRY, 1980, 19 (12) :3655-3663
[2]   Mono- and diboronates derived from tridentate ONO ligands and arylboronic acids [J].
Barba, V ;
Vázquez, J ;
López, F ;
Santillan, R ;
Farfán, N .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (09) :2351-2357
[3]   Two new complexes of phenylboronic acid with N-salicylidene-4-aminobutanol [J].
Barba, V ;
Cuahutle, D ;
Ochoa, ME ;
Santillan, R ;
Farfán, N .
INORGANICA CHIMICA ACTA, 2000, 303 (01) :7-11
[4]   Synthesis and molecular structures of dimeric boron compounds [J].
Barba, V ;
Luna, R ;
Castillo, D ;
Santillan, R ;
Farfán, N .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 604 (02) :273-282
[5]   Stereoselective addition of acetone to the C=N bond of [4.3.0] boron heterobicycles [J].
Barba, V ;
Cuahutle, D ;
Santillan, R ;
Farfán, N .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2001, 79 (08) :1229-1237
[6]   New boron macrocycles based on self-assembly of Schiff bases [J].
Barba, V ;
Gallegos, E ;
Santillan, R ;
Farfán, N .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 622 (1-2) :259-264
[7]  
Beltran H.I., 2001, Rev. Soc. Quim. Mex, V45, P152
[8]   X-ray analysis and structural characterization of 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenones [J].
Beltrán, HI ;
Zamudio-Rivera, LS ;
Mancilla, T ;
Santillan, R ;
Farfán, N .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 657 (1-2) :194-204
[9]   Fixed stereochemical control in the synthesis of new mono- and disubstituted 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenes [J].
Beltrán, HI ;
Alas, SJ ;
Santillan, R ;
Farfán, N .
CANADIAN JOURNAL OF CHEMISTRY, 2002, 80 (07) :801-812
[10]   THE N-B COORDINATION IN HINDERED CYCLIC THEXYLBORONIC ESTERS DERIVED FROM DIETHANOLAMINES [J].
CONTRERAS, R ;
GARCIA, C ;
MANCILLA, T ;
WRACKMEYER, B .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 246 (03) :213-217