Investigation of molecular structure and solvent/temperature effect on tautomerism in (E)-4,6-dibromo-3-methoxy-2-[(p-tolylimino)methyl]phenol, a new thermochromic Schiff base, by using XRD, FT-IR, UV–vis, NMR and DFT methods
Yazarlar (3)
Prof. Dr. Gökhan Kaştaş Samsun Üniversitesi, Türkiye
Prof. Dr. Çiğdem ALBAYRAK KAŞTAŞ Sinop Üniversitesi, Türkiye
Prof. Dr. Ahmet Tabak Sinop 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 (Q1) | ||
| Dergi ISSN | 1386-1425 Dergi Bilgileri (2019) | ||
| Dergi Tarandığı Indeksler | SCI | ||
| Makale Dili | İngilizce | Basım Tarihi | 11-2019 |
| Kabul Tarihi | – | Yayınlanma Tarihi | 01-11-2019 |
| Cilt / Sayı / Sayfa | 222 / 1 / 117198–0 | DOI | 10.1016/j.saa.2019.117198 |
| Makale Linki | https://linkinghub.elsevier.com/retrieve/pii/S1386142519305888 | ||
| UAK Araştırma Alanları |
Organik Kimya
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| Özet |
| The molecular structure and the solvent/temperature effect on the tautomerism in a new Schiff base, (E)-4,6-dibromo-3-methoxy-2-[(p-tolylimino)methyl]phenol, were investigated using spectroscopic (NMR, UV–vis, FT-IR), crystallographic (XRD), computational (DFT and TD-DFT) methods and harmonic oscillator model of aromaticity (HOMA). The XRD, DFT and FT-IR results show that the compound exists in the phenol-imine form in the solid state. HOMA indices support the aromatic structure of the compound. DFT calculations were performed to understand proton transfer process and relatively close values were obtained for the energies of tautomers. UV–vis studies prove the solvent dependence of the tautomerism in the compound by revealing the existence of both phenol-imine and keto-amine forms in polar solvents and only the phenol-imine form in apolar solvent. The TD-DFT results for the electronic transitions lead to the same conclusion as the absorption spectra. 1H NMR and 13C NMR studies at room and low (−60 °C) temperatures indicate that the tautomeric equilibrium occurs rapidly in the compound. Therefore, it is difficult to observe two tautomers. However, the presence of tautomeric structures is clearly seen in acetone‑d |
| Anahtar Kelimeler |
| Computational methods | Schiff Base | Solvent effect | Spectroscopy | Tautomerism | Temperature effect | Thermochromism |
Science Direct
Investigation of molecular structure and solvent/temperature effect on tautomerism in (E)-4,6-dibromo-3-methoxy-2-[(p-tolylimino)methyl]phenol, a new thermochromic Schiff base, by using XRD, FT-IR, UV–vis, NMR and DFT methods
BM Sürdürülebilir Kalkınma Amaçları
| Atıf Sayıları | |
| Web of Science | 22 |
| Scopus | 22 |