Citation: Ya-Nan JIANG, Yuan-Huan DENG, Qiong WANG, Ying-Zhi TAN, Guang-Chuan OU. Chiral recognition of mandelic acid and macrocyclic nickel(Ⅱ) complexes[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(6): 1072-1078. doi: 10.11862/CJIC.2023.073 shu

Chiral recognition of mandelic acid and macrocyclic nickel(Ⅱ) complexes

College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, China

Corresponding author: Guang-Chuan OU, ogcouguangchuan@163.com
Received Date: 27 November 2022
Revised Date: 20 March 2023

Figures(6)

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.
- macrocyclic nickel(Ⅱ) complex,
- chiral recognition,
- mandelic acid,
- 2-phenylpropionic acid,
- tropic acid
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