AZADINIUM SALTS .25. SYMMETRICAL AZOPYRIDINONE DYES - SYNTHESIS, SPECTROPHOTOMETRIC AND ACIDOBASIC PROPERTIES, METAL-COMPLEX FORMATION AND KINETIC INVESTIGATION OF THE AZO-DYE FORMATION

The 13 substituted symmetrical azopyridinone dyes 2a-n were synthesized and their VIS spectra measured. The pK(a)* values of some dyes and of pyridinone coupling components were determined in MeOH/H2O 64:36. The metal-complex formation of the dyes with Cd2+, Zn2+, Co2+, Ni2+, and Cu2+ was investigat...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 77; no. 1; pp. 216 - 230
Main Authors BALLI, H, CHAQUIME, L, HELLRUNG, B, MISUN, M
Format Journal Article
LanguageGerman
Published BASEL NEW SWISS CHEMICAL SOC 01.01.1994
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
HYDRAZONE TAUTOMERISM
1-PHENYLAZO-2-NAPHTHYLAMINE
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Summary:The 13 substituted symmetrical azopyridinone dyes 2a-n were synthesized and their VIS spectra measured. The pK(a)* values of some dyes and of pyridinone coupling components were determined in MeOH/H2O 64:36. The metal-complex formation of the dyes with Cd2+, Zn2+, Co2+, Ni2+, and Cu2+ was investigated, and complex-formation constants of the 1:1 complexes were determined in H2O for 2k (Table 2) and in dimethylformamide/H2O 1:1 for some other azopyridinone dyes (Table 3). The mechanism of the ate-dye formation was investigated and found to be much more complicated than expected. A mechanism of the coupling reaction was developed (see Scheme 4) and fitted by least-squares calculations.
ISSN:0018-019X
DOI:10.1002/hlca.19940770124