Theoretical study on the ground state intramolecular proton transfer (IPT) and solvation effect in two Schiff bases formed by 2-aminopyridine with 2-hydroxy-1- naphthaldehyde and 2-hydroxy salicylaldehyde |
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Authors: | N Tezer N Karakus |
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Institution: | (1) Faculty of Arts and Science, Chemistry Department, Cumhuriyet University, 58140 Sivas, Turkey |
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Abstract: | The tautomerization mechanism the isolated and monohydrated forms of two Schiff bases 1 and 2, and the effect of solvation
on the proton transfer from enol-imine form to the keto-enamine form have been investigated using the B3LYP hybrid density
functional method at the 6-31G** basis set level. The barrier heights for H2O-assisted reactions are significantly lower than that of unassisted tautomerization reaction in the gas phase. Nonspecific
solvent effects have also been taken into account by using the continuum model (IPCM) of four different solvent. The tautomerization
energies and the potential energy barriers are decreased by increasing solvent polarity.
Figure The tautomerization mechanism the isolated and monohydrated forms of two Schiff bases 1 and 2, and the effect of solvation
on the proton transfer from enol-imine form to the keto-enamine form have been investigated using the B3LYP hybrid density
functional method at the 6-31G** basis set level |
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Keywords: | Density functional theory Enol-imine Keto-enamine tautomerizm Schiff bases Solvent effect |
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