Chromatographic approach to study the configurational stability of Ni(II) complexes of amino‐acid Schiff bases possessing stereogenic nitrogen

Jianlin Han (1) , Marion Jean (2) , Christian Roussel (2) , Hiroki Moriwaki (3) , Vadim Soloshonok (4, 5)

1 NFU - Nanjing Forestry University
2 ISM2 - Institut des Sciences Moléculaires de Marseille
3 Hamari Chemicals
4 UPV / EHU - University of the Basque Country = Euskal Herriko Unibertsitatea
5 Ikerbasque - Basque Foundation for Science

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 con-figurational 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.

Keywords: kinetic of racemization; rotational energy barriers; amino acids; axial chirality; chiral HPLC

Domains: Coordination chemistry

Jianlin Han, Marion Jean, Christian Roussel, Hiroki Moriwaki, Vadim Soloshonok. Chromatographic approach to study the configurational stability of Ni(II) complexes of amino‐acid Schiff bases possessing stereogenic nitrogen. Chirality, 2019, 31 (4), pp.328-335. ⟨10.1002/chir.23059⟩. ⟨hal-02514539⟩