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Ab initio modeling of the solvent influence on the azo-hydrazone tautomerism |
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| Authors: | L. Antonov S. Kawauchi M. Satoh J. Komiyama |
| Affiliation: | a National Forestry University, Department of Ecology, 10 Kl. Ohridski avenue, Sofia 1756, Bulgaria b Tokyo Institute of Technology, Department of Polymer Science, O-okayama, Meguro-ku, Tokyo 152, Japan |
| Abstract: | The solvent effect on the azo (A) -hydrazone (H) tautomeric equilibrium of 1-phenylazo-4-naphthol is modeled by using ab initio quantum-chemical calculations. It was found that in methanol, methylene chloride and water there exists a strong hydrogen bonding between the particular tautomer and solvent, as well as dipole–dipole dye-solvent interactions. The results show that the H-form is more stable in water and methylene chloride, while methanol and i-octane stabilize the A-form. The calculational results obtained are in very good agreement with the experimental data in these solvents published previously. |
| Keywords: | Tautomerism Azo dyes Hydrogen bonding Solvent effect |
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