title: Analysis of crystallographic structures of Ni(ii) complexes of α-amino acid Schiff bases: elucidation of the substituent effect on stereochemical preferences.
abstract: In this study, we performed critical analysis of 13 crystallographic structures of various Ni(ii) complexes of amino acid Schiff bases. The major finding of this work is the significance of a parallel displaced type of aromatic interactions between o-amino-benzophenone and Pro N-benzyl rings. The quality of these aromatic interactions was shown to control the steric environment around the amino acid side-chain, rendering variously substituted Ni(ii) complexes of different thermodynamic stabilities. The discovered structural trend holds true for aliphatic, aromatic and sterically bulky amino acids and can be used for the rational design of new and more efficient chiral ligands for general asymmetric synthesis of tailor-made α-amino acids.
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China. hliu@simm.ac.cn and University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Nian
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China. hliu@simm.ac.cn and University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China.
authors.forename: Jiang
authors.initials: J
authors.lastname: Wang
authors.affiliation: Hamari Chemicals Ltd, 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Moriwaki
authors.affiliation: Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain. vadym.soloshonok@ehu.es and IKERBASQUE, Basque Foundation for Science, Maria Diaz de Haro 3, 48013 Bilbao, Spain.
authors.forename: Vadim A
authors.identifier: http://orcid.org/0000-0003-0681-4526
authors.initials: VA
authors.lastname: Soloshonok
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China. hliu@simm.ac.cn and University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China.
authors.forename: Hong
authors.identifier: http://orcid.org/0000-0003-3685-6268
authors.initials: H
authors.lastname: Liu
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001577:Benzophenones / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry*; D003461:Crystallography / Q000379:methods*; D005998:Glycine / Q000737:chemistry; D008024:Ligands; D008968:Molecular Conformation; D009532:Nickel / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000596:Amino Acids; D001577:Benzophenones; D001593:Benzyl Compounds; D056831:Coordination Complexes; D008024:Ligands; D012545:Schiff Bases; C047723:benzophenone; D009532:Nickel; D005998:Glycine