The research of the azo-hydrazone equilibrium by means of AM1 method based on the example of an azo dye - the Schäffer salt derivative

Dyes and Pigments

Volumn 75, Issue 1, 2007, Pages 45-51

  Wojciechowski, K ^a   Szymczak, A ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

AM1; Azo dyes; Azo hydrazone equilibrium; Quantum chemical calculations; Sch ffer salt

Indexed keywords

HYDRATION; QUANTUM CHEMISTRY; SODIUM CHLORIDE; WATER;

AZO-HYDRAZONE EQUILIBRIUM; HYDRAZONE;

AZO DYES;

AZO DYE; CALCULATION; CHEMICAL ANALYSIS; STABILITY;

EID: 34147142885     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2006.05.016     Document Type: Article

References (23)

1. Kelememn J. Azo-hydrazone tautomerism in azo dyes. I. A comparative study of 1-phenylazo-2-naphthol and 1-phenylazo-2-naphthylamine derivatives by electronic spectroscopy. Dyes Pigments 2 2 (1981) 73-91
2. Zollinger H. Color chemistry: syntheses, properties and applications of organic dyes and pigments. 2nd rev. ed. (1991), VCH, Weinheim, New York, Basel, Cambridge
3. Haessner R., Mustroph H., and Bersdorf R. Untersuchungen zum UV/vis-spektralverhalten von azofarbstoffen: VIII-quantitative untersuchungen zur tautomerie substituierter l-phenylazo-2-naphthole mittels UV/vis-spektroskopie. Dyes Pigments 6 4 (1985) 277-291
4. Stoyanov L., and Antonov L. Quantitative analysis of azo-quinonehydrazone tautomeric equilibrium. Dyes Pigments 10 1 (1988) 33-45
5. Antonov L., Kawauchi S., Satoh M., and Komijama J. Ab initio modeling of the solvent influence on the azo-hydrazone tautomerism. Dyes Pigments 40 2-3 (1999) 163-170
6. Gordon P., and Gregory P. Organiczeskaja chimija krasitelej (1987), MIR, Moskwa
7. Schumacher C., Brederek C., and Reidl F. Textilveredlung im wandel der zeit die visionen-die Realitat (1996), 17 IFATCC Congress, Wien
8. Wojciechowski K., and Wolska A. Substantivity and spatial structure of soluble polycyclic dyes for dyeing cellulose fibres. Dyes Pigments 65 2 (2005) 111-116
9. Wojciechowski K., and Szadowski J. Effect of the sulphonic group position on the properties of monoazo dyes. Dyes Pigments 44 2 (2000) 137-147
10. Onsager L. Electric moments of molecules in liquids. J Am Chem Soc 58 2 (1938) 1486-1493
11. Zhou Z., and Parr R.G. Absolute hardness as a measure of aromaticity. Tetrahedron Lett 29 38 (1988) 4843-4846
12. Antonov L.M. Theoretical investigations of the tautomerism of some phenylazonaphthols. 31 UNESCO course for advances research in chemistry and chemical engineering (1996), Tokyo Institute of Technology
13. Cambridge Structural Database, Cambridge Crystallographic Data Center, University Chemical Laboratory, Cambridge.
14. Bernstein I.J., and Ginsburg O.F. Tautomieria w riadu aromaticzeskich azokrasitelej. Usp Khim 41 2 (1972) 177-201 [Russian]
15. Saeva F.D. Tautomeric behavior comparison of 4-phenylazo-1-naphthol and 1-phenylazo-2-napthol systems by nuclear magnetic resonance. J Org Chem 36 24 (1971) 3842-3843
16. Simov D., and Stoyanov S. Electronic spectra and π-electronic structure of some hydroxyazo dyes. J Mol Struct 19 (1973) 255-274
17. Skulski L., and Kleps J. UV-vis and IR spectrophotometric studies on tautomerism of o-amino-, o-acetyloamino-, and o-hydroxymonoazo dyes derived from 2-phenylazonaphthalene and 4-phenylazonaphthalene. Pol J Chem 55 (1981) 1809-1824
18. Berrie A.H., Hampson S.W., Longworth A., and Matias J. Tautomerism in 1-phenylazo-2-naphthols by use of nitrogen-14 nuclear magnetic resonance data. J Chem Soc B (1968) 1308-1310
19. Schreiber J., Socha J., and Rothschein K. Reactivity of organic azo compounds. IX. Tautomerism of some azohydroxy compounds. Coll Czech Chem Commun 35 (1970) 857-866
20. Hihara T., Okada Y., and Morita Z. Azo-hydrazone tautomerism of phenylazonaphthol sulfonates and their analysis using the semiempirical molecular orbital PM5 method. Dyes Pigments 59 1 (2003) 25-41
21. Hikara T., Okada Y., and Morita Z. An analysis of azo-hydrazone tautomerism of reactive azobenzene and pyrazolinyl-azo dyes using the semiempirical molecular orbital PM5 method. Dyes Pigments 61 3 (2004) 199-225
22. Hikara T., Okada Y., and Morita Z. Reactivity of phenylazonaphthol sulfonates, their estimation by semiempirical molecular orbital PM5 method, and the relation between their reactivity and azo-hydrazone tautomerism. Dyes Pigments 59 3 (2003) 201-222
23. Syage J.A. Solvation and vibrational effects on proton tunnelling in clusters. Faraday Discuss (1994) 97401-97413