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Tautomerism, crystal structure, and copper( ii ) complexation of pyridonylazo dyes derived from methyl 4‐aminobenzoate
Author(s) -
Feng YaNan,
Wang YueHua,
Liu YunHong,
Qian HuiFen,
Huang Wei
Publication year - 2017
Publication title -
coloration technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.297
H-Index - 49
eISSN - 1478-4408
pISSN - 1472-3581
DOI - 10.1111/cote.12282
Subject(s) - hydrazone , chemistry , deprotonation , tautomer , pyridine , copper , metal , titration , crystal structure , single crystal , medicinal chemistry , crystallography , polymer chemistry , stereochemistry , ion , inorganic chemistry , organic chemistry
Four heterocyclic dyes, derived from methyl 4‐aminobenzoate and pyridine‐2,4‐dione components, with different N ‐substituents in the latter [ CH 3 , CH 2 CH 3 , CH 2 CH 2 OH , CH 2 CH 2 CH 2 OCH ( CH 3 ) 2 ], were synthesised by the traditional diazotisation‐coupling strategy. Furthermore, a Cu( ii ) dye–metal complex was prepared and characterised by X‐ray single‐crystal diffraction for comparison, where the configuration transformation from hydrazone to deprotonated azo forms was found before and after Cu( ii ) ion complexation. In addition, the azo–hydrazone transformation could be observed by acid–base titration experiments. To the best of our knowledge, this work is the first structural study of pyridone dyes based on methyl 4‐aminobenzoate and the corresponding dye–metal complex.