2-[(2,4-Dimethylphenyl)iminomethyl]-6-methylphenol

Abstract

The title compound, C16H17NO, is a Schiff base which adopts the phenol–imine tautomeric form in the solid state. The mol­ecule is almost planar, with a dihedral angle of 4.61 (4)° between the aromatic rings. The molecular structure is stabilized by an intramolecular O—H⋯N hydrogen bond which generates a six membered ring.

(Z)-2-Methoxy-N-[(5-nitrothiophen-2-yl)methylidene]aniline

“…The deviation from planarity may be due to steric repulsion between the methylene group and phenyl ring. The length of the C5=N2 double bond is 1.266 (3) Å, slightly shorter than standard 1.28 Å value of a C=N double bond and consistent with related structures (Ağar et al, 2010;Tanak et al, 2009;Ceylan et al, 2011).…”

Molecular structure, spectroscopic (FT-IR and UV-Vis) and DFT quantum-chemical studies on 2-[(2,4-Dimethylphenyl)iminomethyl]-6-methylphenol

“…Another difference in the optimised structure is observed in the orientation of the O1-H1 bond, which has an intramolecular O1-H1···N1 hydrogen bond. For the O1-H1···N1 hydrogen bond that exists the phenol O1 atom and imine N1 atom, D-H, H···A and D-H···A values are 0.98(2) Å , 1.65(2) Å , and 157.3 (18) • for X-ray [39] and 0.99 Å , 1.73 Å and 148.12 • for B3LYP, respectively. A logical method for globally comparing the structures obtained with the theoretical calculations is by superimposing the molecular skeleton with that obtained from Xray diffraction, giving an RMSE of 0.723 Å for B3LYP/6-311 ++ G(d,p) ( Figure 3).…”

“…These torsion angles have been calculated at 39.43 • and −143.21 • for the B3LYP/6-311 ++ G(d,p) level, respectively. According to X-ray studies [39], the dihedral angle between the C1/C6 and C9/C14 rings is 4.61 (4) • , whereas the dihedral angle has been calculated at 40.57 • for B3LYP. Another difference in the optimised structure is observed in the orientation of the O1-H1 bond, which has an intramolecular O1-H1···N1 hydrogen bond.…”

“…In a previous publication, the X-ray crystallography of 2-[(2,4-Dimethylphenyl) iminomethyl]-6-methylphenol was studied [39]. In spite of its importance, mentioned above, neither spectroscopic properties nor theoretical calculations of the title compound have been investigated so far.…”

Crystal structure and DFT computational studies of (E)-2,4-di-tert-butyl-6-{[3-(trifluoromethyl)benzyl]iminomethyl}phenol

“…Generally, ortho-hydroxy Schiff base compounds display two tautomeric, enol-imine (OH) and keto-amine (NH), forms. Depending on the tautomers, two types of intramolecular hydrogen bonds are observed in ortho-hydroxy Schiff bases, namely, O-HÁ Á ÁN in enol-imine and N-HÁ Á ÁO in ketoamine tautomers (Tanak et al, 2009(Tanak et al, , 2010. In this study, we report the synthesis, crystal structure and density functional theory (DFT) calculations of the title Schiff base compound.…”