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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| Published in | Helvetica chimica acta Vol. 77; no. 1; pp. 216 - 230 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | German |
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BASEL
NEW SWISS CHEMICAL SOC
01.01.1994
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | CHAQUIME, L BALLI, H HELLRUNG, B MISUN, M |
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| Keywords | HYDRAZONE TAUTOMERISM 1-PHENYLAZO-2-NAPHTHYLAMINE |
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| References | UNVERFERTH, K (WOS:A1971L044800010) 1971; 247 NAEF R (WOS:A1994MW15900022.25) 1991 Job, P (WOS:000201809500003) 1928; 9 PERRIN DD (WOS:A1994MW15900022.27) 1974 LETELLIE.P (WOS:A1970H867500002) 1970; 271 BALLI H (WOS:A1994MW15900022.5) 1990; 73 GELSEMA, WJ (WOS:A19668183000002) 1966; 85 SCHWANDER, HR (WOS:A1982NP67800003) 1982; 3 CHAQUIME L (WOS:A1994MW15900022.8) 1992 GUARESCHI I (WOS:A1994MW15900022.11) 1896; 29 KELEMEN, J (WOS:A1982NC15600003) 1982; 3 HELLRUNG B (WOS:A1994MW15900022.13) SNAVELY, FA (WOS:A1969D865500017) 1969; 8 BALLI, H (WOS:A19668709600013) 1966; 699 RITTER H (WOS:A1994MW15900022.28) 1967 KATRITZKY AR (WOS:A1994MW15900022.16) 1966 WOS:A1994MW15900022.1 LAMM C (WOS:A1994MW15900022.21) 1969 KELEMEN, J (WOS:A1984SF67900001) 1984; 5 MANKU, GCS (WOS:A1972L728500038) 1972; 34 BALLI, H (WOS:A1974T284900027) 1974; 57 OLLINGER H (WOS:A1994MW15900022.26) 1987 ZOLLINGER H (WOS:A1994MW15900022.38) 1987 ALBERT A (WOS:A1994MW15900022.2) 1971 SNAVELY, FA (WOS:A1959WB36700021) 1959; 81 SNAVELY FA (WOS:A1994MW15900022.34) 1969; 33 SNAVELY, FA (WOS:A1959WB36100015) 1959; 81 BALLI, H (WOS:A1978EK49000009) 1978; 61 SZELE, I (WOS:A1983RF48900001) 1983; 112 SNAVELY, FA (WOS:A19679976000016) 1967; 6 GELSEMA, WJ (WOS:A19679944700002) 1967; 86 KELEMEN J (WOS:A1994MW15900022.17) 1981; 2 HORACKOVA, J (WOS:A1991FE91200014) 1991; 56 BALLI, H (WOS:A19614457A00002) 1961; 647 SNAYELY FA (WOS:A1994MW15900022.35) 1957; 73 MISUN M (WOS:A1994MW15900022.24) 1988 HELLRUNG B (WOS:A1994MW15900022.12) 1969 KELEMEN, J (WOS:A1982PH50700001) 1982; 3 |
| References_xml | – volume: 73 start-page: 491 year: 1957 ident: WOS:A1994MW15900022.35 publication-title: J DYERS COLOURISTS contributor: fullname: SNAYELY FA – volume: 3 start-page: 133 year: 1982 ident: WOS:A1982NP67800003 article-title: HETEROCYCLIC AZO COUPLING COMPONENTS publication-title: DYES AND PIGMENTS contributor: fullname: SCHWANDER, HR – volume: 699 start-page: 133 year: 1966 ident: WOS:A19668709600013 article-title: AZIDINIUMSALZE .V. SYMMETRISCHE AZOPYRAZOLON-(5)-FARBSTOFFE DURCH AZOGRUPPEN-UBERTRAGUNG HETEROCYCLISCHER AZIDINIUMSALZE AUF 1-[X-PHENYL]-3-METHYL-PYRAZOLONE-(5) publication-title: ANNALEN DER CHEMIE-JUSTUS LIEBIG contributor: fullname: BALLI, H – year: 1971 ident: WOS:A1994MW15900022.2 publication-title: DETERMINATION IONIZA contributor: fullname: ALBERT A – volume: 8 start-page: 1659 year: 1969 ident: WOS:A1969D865500017 article-title: METAL DERIVATIVES OF ARYLAZOPYRAZOLONE COMPOUNDS .8. MOLARITY QUOTIENTS OF SULFONIC ACID DERIVATIVES OF AZO-3- AND AZO-5-PYRAZOLONES publication-title: INORGANIC CHEMISTRY contributor: fullname: SNAVELY, FA – volume: 271 start-page: 1208 year: 1970 ident: WOS:A1970H867500002 article-title: VARIATIONS OF IONIZATION ENTHALPIES AND ENTROPIES OF VARIOUS ANILINES IN WATER AND METHANOL MIXTURES publication-title: COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C contributor: fullname: LETELLIE.P – volume: 73 start-page: 1679 year: 1990 ident: WOS:A1994MW15900022.5 publication-title: HELV CHIM ACTA contributor: fullname: BALLI H – ident: WOS:A1994MW15900022.1 – year: 1969 ident: WOS:A1994MW15900022.12 publication-title: THESIS U BASEL contributor: fullname: HELLRUNG B – volume: 112 start-page: 1 year: 1983 ident: WOS:A1983RF48900001 article-title: AZO COUPLING REACTIONS STRUCTURES AND MECHANISMS publication-title: TOPICS IN CURRENT CHEMISTRY contributor: fullname: SZELE, I – volume: 81 start-page: 2337 year: 1959 ident: WOS:A1959WB36100015 article-title: METAL DERIVATIVES OF AZO PYRAZOLONE DYES .2. MOLARITY QUOTIENTS OF AZO PYRAZOLONE DYES CONTAINING ORTHO-METHOXY AND ORTHO-THIOMETHOXY GROUPS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: SNAVELY, FA – volume: 86 start-page: 852 year: 1967 ident: WOS:A19679944700002 article-title: PH-MEASUREMENTS IN ALCOHOL-WATER MIXTURES . ON USE OF AQUEOUS STANDARD BUFFER SOLUTIONS FOR CALIBRATION publication-title: RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS contributor: fullname: GELSEMA, WJ – volume: 3 start-page: 27 year: 1982 ident: WOS:A1982NC15600003 article-title: AZO-HYDRAZONE TAUTOMERISM IN AZO DYES .2. RAMAN, NMR AND MASS-SPECTROMETRIC INVESTIGATIONS OF 1-PHENYLAZO-2-NAPHTHYLAMINE AND 1-PHENYLAZO-2-NAPHTHOL DERIVATIVES publication-title: DYES AND PIGMENTS contributor: fullname: KELEMEN, J – volume: 29 start-page: 655 year: 1896 ident: WOS:A1994MW15900022.11 publication-title: BER DTSCH CHEM GES contributor: fullname: GUARESCHI I – volume: 2 start-page: 73 year: 1981 ident: WOS:A1994MW15900022.17 publication-title: DYES PIGMENTS contributor: fullname: KELEMEN J – volume: 81 start-page: 4199 year: 1959 ident: WOS:A1959WB36700021 article-title: METAL DERIVATIVES OF ARYL AZO PYRAZOLONE DYES .3. MOLARITY QUOTIENTS OF PARA-SUBSTITUTED AND META-SUBSTITUTED PYRAZOLONE DYES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: SNAVELY, FA – year: 1991 ident: WOS:A1994MW15900022.25 publication-title: CIBA GEIGY AG contributor: fullname: NAEF R – volume: 9 start-page: 113 year: 1928 ident: WOS:000201809500003 article-title: Studies on the formation of complex minerals in solution and on their stability. publication-title: ANNALES DE CHIMIE FRANCE contributor: fullname: Job, P – start-page: 566 year: 1966 ident: WOS:A1994MW15900022.16 publication-title: J CHEM SOC B contributor: fullname: KATRITZKY AR – volume: 85 start-page: 647 year: 1966 ident: WOS:A19668183000002 article-title: PH-MEASUREMENTS IN ALCOHOL-WATER MIXTURES USING AQUEOUS STANDARD BUFFER SOLUTIONS FOR CALIBRATION publication-title: RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS contributor: fullname: GELSEMA, WJ – volume: 56 start-page: 386 year: 1991 ident: WOS:A1991FE91200014 article-title: AZO COUPLING KINETICS OF BENZENEDIAZONIUM IONS WITH CITRAZINIC ACID publication-title: COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS contributor: fullname: HORACKOVA, J – volume: 61 start-page: 97 year: 1978 ident: WOS:A1978EK49000009 article-title: DIAZO-GROUP TRANSFER TO ACTIVE METHYLENE-COMPOUNDS USING AZIDINIUM SALTS publication-title: HELVETICA CHIMICA ACTA contributor: fullname: BALLI, H – volume: 647 start-page: 11 year: 1961 ident: WOS:A19614457A00002 article-title: AZIDINIUMSALZE, .2. STRUKTUR UND REAKTIVITAT QUASIAROMATISCHER AZIDOCYCLIMONIUM-FLUOROBORATE publication-title: ANNALEN DER CHEMIE-JUSTUS LIEBIG contributor: fullname: BALLI, H – year: 1969 ident: WOS:A1994MW15900022.21 publication-title: THESIS U BASEL contributor: fullname: LAMM C – year: 1974 ident: WOS:A1994MW15900022.27 publication-title: BUFFERS PH METAL ION contributor: fullname: PERRIN DD – volume: 3 start-page: 249 year: 1982 ident: WOS:A1982PH50700001 article-title: AZO-HYDRAZONE TAUTOMERISM IN AZO DYES .3. THE TAUTOMERIC STRUCTURE OF 1-(4'-NITROPHENYLAZO)-2-NAPHTHYLAMINE FROM CRYSTAL-STRUCTURE DETERMINATION publication-title: DYES AND PIGMENTS contributor: fullname: KELEMEN, J – ident: WOS:A1994MW15900022.13 publication-title: UNPUB contributor: fullname: HELLRUNG B – volume: 6 start-page: 1831 year: 1967 ident: WOS:A19679976000016 article-title: A STUDY OF EFFECT OF STERIC HINDRANCE IN METAL COORDINATION WITH AZO-3-PYRAZOLONES publication-title: INORGANIC CHEMISTRY contributor: fullname: SNAVELY, FA – year: 1992 ident: WOS:A1994MW15900022.8 publication-title: THESIS U BASEL contributor: fullname: CHAQUIME L – volume: 34 start-page: 1091 year: 1972 ident: WOS:A1972L728500038 article-title: FORMATION CONSTANTS OF SOME BIVALENT ION COMPLEXES WITH 1-(SUBSTITUTED PHENYLAZO)-2-NAPHTHOLS IN AQUEOUS ACETONE publication-title: JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY contributor: fullname: MANKU, GCS – volume: 5 start-page: 83 year: 1984 ident: WOS:A1984SF67900001 article-title: AZO HYDRAZONE TAUTOMERISM IN AZO DYES .4. COLOR AND TAUTOMERIC STRUCTURE OF ADSORBED 1-PHENYLAZO-2-NAPHTHYLAMINE AND 1-PHENYLAZO-2-NAPHTHOL DYES publication-title: DYES AND PIGMENTS contributor: fullname: KELEMEN, J – year: 1988 ident: WOS:A1994MW15900022.24 publication-title: THESIS U BASEL contributor: fullname: MISUN M – year: 1967 ident: WOS:A1994MW15900022.28 publication-title: THESIS U BASEL contributor: fullname: RITTER H – volume: 33 start-page: 513 year: 1969 ident: WOS:A1994MW15900022.34 publication-title: J ORG CHEM contributor: fullname: SNAVELY FA – start-page: 85 year: 1987 ident: WOS:A1994MW15900022.26 publication-title: COLOR CHEM contributor: fullname: OLLINGER H – volume: 57 start-page: 1178 year: 1974 ident: WOS:A1974T284900027 article-title: AZIDINIUM SALTS .10. STRUCTURAL AND REACTIVITY CORRELATIONS IN QUATERNARY N-HETEROAROMATIC COMPOUNDS - DIAZO GROUP TRANSFER-REACTION OF HETEROCYCLIC AZIDINIUM SALTS ON 1-(PARA-SULFOPHENYL)-3-METHYL-PYRAZOLIN-5-ONE AND 1-(META-SULFOPHENYL)-3-METHYL-5-AMINOPYRAZOLE publication-title: HELVETICA CHIMICA ACTA contributor: fullname: BALLI, H – year: 1987 ident: WOS:A1994MW15900022.38 publication-title: COLOR CHEM contributor: fullname: ZOLLINGER H – volume: 247 start-page: 302 year: 1971 ident: WOS:A1971L044800010 article-title: HAMMETT ACIDITY FUNCTION H0 IN METHANOL-WATER MIXTURE publication-title: ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE-LEIPZIG contributor: fullname: UNVERFERTH, K |
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| Title | AZADINIUM SALTS .25. SYMMETRICAL AZOPYRIDINONE DYES - SYNTHESIS, SPECTROPHOTOMETRIC AND ACIDOBASIC PROPERTIES, METAL-COMPLEX FORMATION AND KINETIC INVESTIGATION OF THE AZO-DYE FORMATION |
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