Synthesis, characterization and computational studies of 3-{(E)-[(2-hydroxyphenylimino]methyl}benzene-l,2-diol and molecular structure of its zwitterionic form

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Atıf İçin Kopyala

Ezeorah J. C., Ossai V., Obasi L. N., Elzagheid M. I., Rhyman L., Lutter M., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1152, ss.21-28, 2018 (SCI-Expanded)

• Yayın Türü: Makale / Tam Makale
• Cilt numarası: 1152
• Basım Tarihi: 2018
• Doi Numarası: 10.1016/j.molstruc.2017.09.083
• Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
• Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Sayfa Sayıları: ss.21-28
• Anahtar Kelimeler: Schiff base, X-ray crystallography, DFT, Zwitterionic, 2,3-Dihydroxybenzaldehyde, GRAPH-SET ANALYSIS, PROTON-TRANSFER, SCHIFF-BASES, SOLID-STATE, COMPLEXES, TAUTOMERIZATION, PATTERNS, SOLVENT, IMINES, ANILS
• Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

The Schiff base 3-{(E)-[(2-hydroxyphenyl)imino]methyl}benzene-l,2-diol was synthesized by the condensation of 2,3-dihydroxybenzaldehyde and 2-aminophenol in water at room temperature. The crystal was grown using two solvents (dry methanol and 60% methanol). The compound was characterized using elemental microanalysis, IR, NMR, UV spectroscopies and single-crystal X-ray diffraction crystallography. The X-ray structure reveals that the Schiff base crystallizes as a methanol solvate in dry methanol with triclinic crystal system, space group P-1 and Z = 2 in the unit cell and as a non-methanol solvate in 60% methanol with triclinic crystal system, space group P-1 and Z = 4 in the unit cell. The compound showed absorption bands at 272,389,473 and 602 nm in DMSO. These bands were assigned as n -> pi*, n -> pi* and n ->pi* transitions. The 473 and 602 nm bands in DMSO reveal that the compound exists in tautomeric forms. The presence of N-H, C-O and C=N stretching vibrations in the IR spectrum indicates that the compound is zwitterionic in the solid state. This study was supplemented using density functional theory method.