Chinese Version
Home | About Journal | Editorial Board | Information for Authors | Copyright Transfer Statement | Contact us
Chiral recognition of mandelic acid and macrocyclic nickel(Ⅱ) complexes
Author NameAffiliationE-mail
JIANG Ya-Nan College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, China  
DENG Yuan-Huan College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, China  
WANG Qiong College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, China  
TAN Ying-Zhi College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, China  
OU Guang-Chuan College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, China ogcouguangchuan@163.com 
Abstract: The reactions of a racemic four-coordinated macrocyclic nickel(Ⅱ) complex[Ni(rac-L)](ClO4)2 with l- and d-mandelic acid anion in acetonitrile/water gave six-coordinated enantiomers of[Ni(RR-L) (S-Man)]ClO4 (1) and[Ni(SS-L)(R-Man)]ClO4 (2) (L=5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, Man=mandelic acid), respectively. The reaction of[Ni(rac-L)](ClO4)2 with dl-Man- gave a conglomerate, in which the RR and SS enantiomers preferentially coordinate to l- and d-Man- respectively to give a racemic mixture of 1 and 2, and the chiral recognition occurs during the reaction, in which each crystal crystallizes into enantiopure. The reactions of[Ni(rac-L)] (ClO4)2 with dl-2-phenylpropionic acid and tropic acid anion gave complexes[Ni(rac-L)(dl-PPA)]ClO4 (3) (PPA=2-phenylpropionic acid) and[Ni(rac-L)(dl-Tro)]ClO4 (4) (Tro=tropic acid), respectively. Single-crystal X-ray diffraction analyses show that the Ni (Ⅱ) ions display an octahedral coordination geometry by coordination with four nitrogen atoms of macrocyclic ligand in a folded configuration, plus two oxygen atoms of carboxyl and hydroxyl for 1 and 2, or two oxygen atoms of carboxyl for 3 and 4 in cis-position. Complexes 1 and 2 belong to a pair of enantiomers, which are constructed via hydrogen bonding linking of[Ni(RR-L)(S-Man)]+ and[Ni(SS-L)(R-Man)]+ monomers to form 1D hydrogen bonded zigzag chain, respectively. The homochiral natures of 1 and 2 are confirmed by the results of circular dichroism (CD) spectra measurements. CCDC:2220158, 1; 2220159, 2; 2220160, 3; 2220161, 4.
Keywords: macrocyclic nickel(Ⅱ) complex  chiral recognition  mandelic acid  2-phenylpropionic acid  tropic acid
Hits:  3231
Download times:  1180
JIANG Ya-Nan,DENG Yuan-Huan,WANG Qiong,TAN Ying-Zhi,OU Guang-Chuan.Chiral recognition of mandelic acid and macrocyclic nickel(Ⅱ) complexes[J].Chinese Journal of Inorganic Chemistry,2023,39(6):1072-1078.
View Full Text  View/Add Comment  Download reader
Chinese Journal of Inorganic Chemistry