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| - Effect of Cooperative Hydrogen Bonding in Azo−Hydrazone Tautomerism of Azo Dyes
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| - Azo−hydrazone tautomerism in azo dyes has been modeled by using density functional theory (DFT) at theB3LYP/6-31+G(d,p) level of theory. The most stable tautomer was determined both for model compoundsand for azo dyes Acid Orange 7 and Solvent Yellow 14. The effects of the sulfonate group substitution andthe replacement of the phenyl group with naphthyl on the tautomer stability and on the behavior in solventhave been discussed. Intramolecular hydrogen bond energies have been estimated for the azo and hydrazonetautomers to derive a relationship between the tautomer stability and the hydrogen bond strength. The transitionstructures for proton transfer displayed resonance assisted strong hydrogen bonding properties within theframework of the electrostatic-covalent hydrogen bond model (ECHBM). Evolution of the intramolecularhydrogen bond with changing structural and environmental factors during the tautomeric conversion processhas been studied extensively by means of the atoms-in-molecules (AIM) analysis of the electron density. Thebulk solvent effect was examined using the self-consistent reaction field model. Special solute−solventinteractions were further investigated by means of quantum mechanical calculations after defining the first-solvation shell by molecular dynamics simulations. The effect of cooperative hydrogen bonding with solventmolecules on the tautomer stability has been discussed.
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