title: The prototropic tautomerism and substituent effect through strong electron-withdrawing group in (E)-5-(diethylamino)-2-[(3-nitrophenylimino)methyl]phenol.
abstract: The prototropic tautomerism in o-Hydroxy Schiff bases results in two forms called phenol-imine and keto-amine. The preference of a particular form by the compound changes in the solid and solvent media. The choice can also be regulated by a substituent with a different electron-donating or withdrawing group. In the present study, the above-mentioned factors are considered in the investigation of (E)-5-(diethylamino)-2-[(3-nitrophenylimino)methyl]phenol compound (an o-Hydroxy Schiff basis) by experimental (XRD, FT-IR and UV-vis) and computational (DFT and TD-DFT) methods. The results show that the title compound adopts only phenol-imine form in the solid and solvent media. This was attributed to the substituent effect through strong electron-withdrawing nitro group.
authors.affiliation: Sinop University, Faculty of Education, 57000 Sinop, Turkey. calbayrak@sinop.edu.tr
authors.forename: Ciğdem
authors.initials: C
authors.lastname: Albayrak
authors.forename: Gökhan
authors.initials: G
authors.lastname: Kaştaş
authors.forename: Mustafa
authors.initials: M
authors.lastname: Odabaşoğlu
authors.forename: Rene
authors.initials: R
authors.lastname: Frank
mesh_terms: D007097:Imines / Q000737:chemistry*; D008745:Methylation; D008958:Models, Molecular; D010636:Phenols / Q000737:chemistry*; D011522:Protons; D012545:Schiff Bases / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
chemical_list: D007097:Imines; D010636:Phenols; D011522:Protons; D012545:Schiff Bases
keywords: Computational study; DFT; FT-IR; Intramolecular proton transfer; Schiff base; UV–vis