title: Existence of a resonance hybrid structure as a result of proton tautomerism in (±)-(E)-4-bromo-2-[(2,3-dihydroxypropylimino) methyl]phenol racemate.
abstract: o-Hydroxy Schiff bases have two tautomers known as phenol-imine and keto-amine forms. In the present work, the tautomerism in (E)-4-Bromo-2-[(2,3-dihydroxypropylimino)methyl]phenol compound has been investigated by experimental (XRD, FT-IR and UV-vis) and computational (DFT and TD-DFT) methods. The X-ray diffraction (XRD) study reveals that the title compound favors a resonance hybrid structure of phenol-imine and keto-amine forms in the solid state rather than having these forms separately or jointly. Experimental UV-vis study of proton transfer process in solvent media (Benzene, DMSO and EtOH) shows the preference of phenol-imine form in benzene while both phenol-imine and keto-amine characteristics are present in EtOH and DMSO.
authors.affiliation: Sinop University, Faculty of Arts and Sciences, Department of Chemistry, 57000 Sinop, Turkey. Electronic address: calbayrak@sinop.edu.tr.
authors.forename: Çiğdem
authors.initials: Ç
authors.lastname: Albayrak
authors.affiliation: Ondokuz Mayıs University, Civil Aviation College, Samsun, Turkey.
authors.forename: Gökhan
authors.initials: G
authors.lastname: Kaştaş
authors.affiliation: Pamukkale University, Chemical Technology Program, 20070 Kınıklı-Denizli, Turkey.
authors.forename: Mustafa
authors.initials: M
authors.lastname: Odabaşoğlu
authors.affiliation: Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139 Kurupelit-Samsun, Turkey.
authors.forename: Orhan
authors.initials: O
authors.lastname: Büyükgüngör
mesh_terms: D000588:Amines / Q000737:chemistry; D018360:Crystallography, X-Ray; D054879:Halogenation; D007097:Imines / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D010636:Phenols / Q000737:chemistry*; D011522:Protons; D012545:Schiff Bases / Q000737:chemistry*
chemical_list: D000588:Amines; D007097:Imines; D010636:Phenols; D011522:Protons; D012545:Schiff Bases
keywords: Enantiomer; Keto-amine; Phenol-imine; Schiff Base; Tautomerism; X-ray