Analysis of tautomeric equilibrium in (E)-4,6-dibromo-2-[(4-fluorophenylimino)methyl]-3-methoxyphenol compound
Yazarlar (5)
Çiʇdem Albayrak Kaştaş
Sinop Üniversitesi, Türkiye
Gökhan Kaştaş Ondokuz Mayis Üniversitesi, Türkiye
Prof. Dr. Mahmut GÜR Kastamonu Üniversitesi, Türkiye
Halit Muʇlu
Kastamonu Üniversitesi, Türkiye
Orhan Büyükgüngör Ondokuz Mayis Üniversitesi, Türkiye
Makale Türü Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy
Dergi ISSN 1386-1425 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler SCI
Makale Dili İngilizce Basım Tarihi 12-2015
Cilt / Sayı / Sayfa 151 / 1 / 731–738 DOI 10.1016/j.saa.2015.07.030
Makale Linki https://linkinghub.elsevier.com/retrieve/pii/S1386142515300810
UAK Araştırma Alanları
Organik Kimya
Özet
In this study, the tautomeric equilibrium between the phenol-imine and keto-amine structural forms of (E)-4,6-dibromo-2-[(4-fluorophenylimino)methyl]-3-methoxyphenol compound has been investigated with experimental (XRD, UV–vis and NMR) and theoretical (DFT and TD-DFT) methods. The results clearly show that structural preference of the compound is definitely depended on its state. Namely, the compound exists in phenol-imine form in the solid state while one or both of these forms can be seen in solvent media. For example, the compound prefers phenol-imine form in benzene while both forms exist in EtOH and DMSO solvents. Coexistence of two forms has been quantified with NMR studies, giving a ratio of 11:9 for phenol and keto structures of the compound in acetone-d6 solvent.
Anahtar Kelimeler
Keto-amine | NMR | Phenol-imine | Schiff base | Tautomerism | X-ray