The prototropic tautomerism and substituent effect through strong electron-withdrawing group in (E)-5-(diethylamino)-2-(3-nitrophenylimino)methyl] phenol

Albayrak, Çiǧdem; KAŞTAŞ, GÖKHAN; Odabaşoǧlu, Mustafa; Frank, Rene

doi:10.1016/j.saa.2013.05.044

The prototropic tautomerism and substituent effect through strong electron-withdrawing group in (E)-5-(diethylamino)-2-(3-nitrophenylimino)methyl] phenol

Albayrak Ç., KAŞTAŞ G., Odabaşoǧlu M., Frank R.

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, cilt.114, ss.205-213, 2013 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 114
Basım Tarihi: 2013
Doi Numarası: 10.1016/j.saa.2013.05.044
Dergi Adı: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.205-213
Anahtar Kelimeler: Computational study, DFT, FT-IR, Intramolecular proton transfer, Schiff base, UV-vis
Samsun Üniversitesi Adresli: Hayır

Özet

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. © 2013 Elsevier B.V. All rights reserved.