X-ray crystallographic study of boroxazolidones obtained from L-ornithine, L-methionine, kainic acid and 2,6-pyridinedicarboxylic acid

被引:26
作者
Trujillo, J
Hopfl, H
Castillo, D
Santillan, R
Farfan, N
机构
[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico
[2] IPN, Escuela Super Med, Secc Graduados, Mexico City 11340, DF, Mexico
[3] IPN, Escuela Super Med, Dept Bioquim, Mexico City 11340, DF, Mexico
[4] Univ Autonoma Estado Morelos, Ctr Invest Quim, Cuernavaca 62210, Morelos, Mexico
关键词
alpha-amino acids; kainic acid; boron complexes; boroxazolidones; boroxazolidines; hydrolytic stability;
D O I
10.1016/S0022-328X(98)00893-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In the present contribution, the boroxazolidones prepared from L-ornithine, L-methionine, kainic acid and 2,6-pyridinedicarboxylic acid have been studied by X-ray crystallography. A comparison of the structural data with corresponding boroxazolidines, bicyclic boronates and tricyclic berates has shown that in boron complexes with a boroxazolidone ring the B-O bond is longer in comparison to boron complexes with a boroxazolidine ring. At the same time the N-->B bond length is shorter indicating that the hydrolytic stability of the complexes with boroxazolidone rings is enhanced. (C) 1998 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:21 / 29
页数:9
相关论文
共 25 条
[1]   TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].
ALLEN, FH ;
KENNARD, O ;
WATSON, DG ;
BRAMMER, L ;
ORPEN, AG ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19
[2]   CHIRAL SYNTHESIS VIA ORGANOBORANES .16. BOROXAZOLIDONES DERIVED FROM ALPHA-AMINO-ACIDS AND BORINIC OR BORONIC ESTERS - A SIMPLE PROCEDURE FOR UPGRADING BORINATES AND BORONATES TO MATERIALS OF HIGH OPTICAL PURITY [J].
BROWN, HC ;
GUPTA, AK .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 341 (1-3) :73-81
[3]   PREPARATION AND STORAGE OF DIPHENYLBORINIC ACID AND ITS ANHYDRIDE [J].
CHREMOS, GN ;
WEIDMANN, H ;
ZIMMERMAN, HK .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05) :1683-&
[4]   NMR AND X-RAY-DIFFRACTION STUDIES OF 2 BICYCLIC BORATES CONTAINING CHIRAL BORON AND NITROGEN-ATOMS [J].
FARFAN, N ;
MANCILLA, T ;
CASTILLO, D ;
URIBE, G ;
CARRILLO, L ;
JOSEPHNATHAN, P ;
CONTRERAS, R .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 381 (01) :1-13
[5]   THROUGH-BOND MODULATION OF N-]B RING FORMATION SHOWN BY NMR AND X-RAY-DIFFRACTION STUDIES OF BORATE DERIVATIVES OF PYRIDYL ALCOHOLS [J].
FARFAN, N ;
CASTILLO, D ;
JOSEPHNATHAN, P ;
CONTRERAS, R ;
VONSZENTPALY, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04) :527-532
[6]  
FARFAN N, 1982, NOUV J CHIM, V6, P269
[7]   NMR-STUDIES OF 1,1-DIPHENYLBOROXAZOLIDONE DERIVATIVES OF ALPHA-AMINO-ACIDS [J].
FARFAN, N ;
SILVA, D ;
SANTILLAN, R .
HETEROATOM CHEMISTRY, 1993, 4 (06) :533-536
[9]  
HALSTROM J, 1978, J CHEM RES-S, P80
[10]  
Hopfl H, 1998, J MOL STRUC-THEOCHEM, V427, P1, DOI 10.1016/S0166-1280(97)00087-0