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Chromatographic approach to study the configurational stability of Ni(II) complexes of amino‐acid Schiff bases possessing stereogenic nitrogen
Author(s) -
Han Jianlin,
Jean Marion,
Roussel Christian,
Moriwaki Hiroki,
Soloshonok Vadim A.
Publication year - 2019
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23059
Subject(s) - stereocenter , chemistry , schiff base , nitrogen , glycine , solvent , amino acid , high performance liquid chromatography , chromatography , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry
Abstract Herein, we disclose the design of a model Ni(II) complex of glycine Schiff base possessing single‐nitrogen stereogenic center, which was successfully used for high‐performance liquid chromatography (HPLC)‐assisted assessment of its configurational stability. The major finding is that the configurational stability of the Ni(II)‐coordinated nitrogen is profoundly dependent on the reaction conditions used, in particular the solvent, and can range from inconsequential ( t ½ less than 5 min) to virtually completely stable ( t ½ 90 y). The discovery reported in this study most likely to be of certain theoretical and synthetic value.