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Synthesis, structure and property of diorganotin N ‐[(3‐methoxy‐2‐oxyphenyl)methylene]tyrosinates
Author(s) -
Tian Laijin,
Han Lu,
Yao Yanze,
Zheng Xiaoliang,
Liu Xijie,
Lin Xianjie
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4475
Subject(s) - chemistry , trigonal bipyramidal molecular geometry , crystallography , methylene , supramolecular chemistry , molecule , tin , crystal structure , octahedron , stereochemistry , hydrogen bond , octahedral molecular geometry , steric effects , intermolecular force , intramolecular force , medicinal chemistry , organic chemistry
Five new diorganotin N ‐[(3‐methoxy‐2‐oxyphenyl)methylene] tyrosinates, R 2 Sn[2‐O‐3‐MeOC 6 H 3 CH=NCH (CH 2 C 6 H 4 OH‐4)COO] (R = Me, 1 ; Et, 2 ; Bu, 3 ; Cy, 4 ; Ph, 5 ), have been synthesized and characterized by elemental analysis, IR, NMR ( 1 H, 13 C and 119 Sn) spectra, and the X‐ray single crystal diffraction. In non‐coordinated solvent, complexes 1 – 5 have penta‐coordinated tin atom. In the solid state, 1 – 3 are centrosymmetric dimmers in which each tin atom is seven‐coordinated in a distorted pentagonal bipyramid, and 4 displays discrete molecular structure with distorted trigonal bipyramidal geometry, and the tin atom of 5 is hexa‐coordinated and possess the distorted octahedral geometry with a coordinational methanol molecule. The intermolecular O‐H⋅⋅⋅O hydrogen bonds in 1 – 4 link molecules into the different one‐dimensional supramolecular chain with R 2 2 (30) or R 2 2 (20) macrocycles, and the molecules of 5 are joined into a two‐dimensional supramolecular network containing R 4 4 (24) and R 4 4 (28) two macrocycles. Bioassay results against human tumour cell HeLa indicated that 3 ‐ 5 belonged to the efficient cytostatic agents and the activity decreased in the order 4 > 3 > 5 > 2 > 1. The fluorescence determinations show the complexes may be explored for potential luminescent materials.