Spectroscopy and visible-light driven photocatalytic properties of a microcrystalline Cu-complex derived from a novel Gabapentin Schiff base

Wang, Dawei; Wang, Tao; Yang, Haiyan; Yang, Jing; Shi, Zhengjun

doi:10.1016/j.saa.2023.123138

Cited by 6 publications

(1 citation statement)

References 38 publications

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“…S1 ), the broad characteristic band at 3455 cm −1 can be assigned to the –OH groups of the two alcoholic arms 58 – 60 . The imine bond vibration (υC=N) is observed as a strong band at 1657 cm −1 which confirms the successful formation of the Schiff base ligand 61 – 63 In the 1 H NMR spectrum of HL (see Fig. S2 ), the singlet peak at 8.11 ppm corresponds to the imine group, which can confirm the presence of CH=N group in the structure of this compound.…”

Section: Resultsmentioning

confidence: 53%

Synthesis of chiral Cu(II) complexes from pro-chiral Schiff base ligand and investigation of their catalytic activity in the asymmetric synthesis of 1,2,3-triazoles

Ajormal,

Bikas,

Noshiranzadeh

et al. 2024

Sci Rep

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A pro-chiral Schiff base ligand (HL) was synthesized by the reaction of 2-amino-2-ethyl-1,3-propanediol and pyridine-2-carbaldehyde in methanol. The reaction of HL with CuCl2·2H2O and CuBr2 in methanol gave neutral mononuclear Cu(II) complexes with general formula of [Cu(HL)Cl2] (1) and [Cu(HL)Br2] (2), respectively. By slow evaporation of the methanolic solutions of 1 and 2, their enantiomers were isolated in crystalline format. The formation of pure chiral crystals in the racemic mixture was amply authenticated by single crystal X-ray analysis, which indicated that S-[Cu(HL)Cl2], R-[Cu(HL)Cl2], and S-[Cu(HL)Br2] are crystallized in chiral P212121 space group of orthorhombic system. Preferential crystallization was used to isolate the R and S enantiomers as single crystals and the isolated compounds were also studied by CD analysis. Structural studies indicated that the origin of the chirality in these compounds is related to the coordination mode of the employed pro-chiral ligand (HL) because one of its carbon atoms has been converted to a chiral center in the synthesized complexes. Subsequently, these complexes were used in click synthesis of a β-hydroxy-1,2,3-triazole and the results of catalytic studies indicated that 1 and 2 can act as enantioselective catalysts for the asymmetric synthesis of β-hydroxy-1,2,3-triazole product under mild condition. This study illustrates the significant capacity of the use of pro-chiral ligands in preparing chiral catalysts based on complexes which can also be considered as an effective approach to cheap chiral catalysts from achiral reagents.

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