ermiş, emel anadolu university - science faculty - department of chemistry, TURKEY

MICROWAVE ASSISTED SYNTHESIS and CHARACTERIZATION of 6,6 - {OXYBIS [(p- PHENYLENE)IMINOMETHYL]}BIS-(2-tert-BUTYL PHENOL), EXPERIMENTAL and THEORETICAL INVESTIGATION of ITS TAUTOMERIC AND SOLVATOCHROMIC PROPERTIES

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The synthesis of 6,6 -{oxybis[(p-phenylene)iminomethyl]}bis-(2-tert-butylphenol) (3) was performed from the condensation reaction of 3-tert-butylsalicylaldehyde (1) with 4,4 -diaminodiphenyl ether (2) using the microwave-irradiation method. The structure of compound (3) was characterized by elemental analysis, FTIR, 1H NMR, 13C NMR and UV-visible spectroscopic techniques. The tautomeric equilibria (for phenol-imine O−H....N and keto-amine O....H−N tautomers) and the behavior of solvatochromic in different organic solvents were studied using UV-visible spectrophotometric method. Furthermore, the structure of compound, the energies of phenol-imine/ phenol-imine and keto-amine/keto-amine tautomers in different organic solvents, intramolecular O−H....N and O....H−N hydrogen bond length, UV-visible excitation energy and oscillator strength were calculated with the theoretical DFT method (B3LYP)/6-311+G(d,p) and calculations were compared with experimental results. It was determined theoretically and experimentally that the compound (3) exhibits the phenol-imine/phenol-imine tautomeric structure and solvatochromic feature in selected organic solvents.

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4 , 4 , Diaminodiphenyl ether , Microwave , irradiation method , Tautomeric equilibrium , Solvatochromism , DFT

Anadolu University Journal of Science and Technology. A : Applied Sciences and Engineering

95