Similarities and differences between azomethines and ketimines: Synthesis, materials characterization and structure of novel imines compounds

Iwan, Agnieszka; Kaczmarczyk, Bożena; Janeczek, Henryk; Sęk, Danuta; Ostrowski, Sławomir

doi:10.1016/j.saa.2006.05.016

Cited by 20 publications

(8 citation statements)

References 22 publications

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“…In order to estimate the impact of the furan ring on the optical properties of the Schiff bases, model compounds 7 and 8 were synthesized by reaction of DFF or terephthaldehyde (OHC–Ph–CHO) with aniline. Consistent with a literature report, benzylideneaniline 8 shows two bands in its UV‐visible absorption spectrum at about 295 and 342 nm, possibly attributed to π–π * and n− π * transitions. In sharp contrast, the absorption spectrum of 7 reveals one broad peak with λ max ≈ 367 nm (Fig.…”

Section: Resultssupporting

confidence: 91%

Schiff base polymers derived from 2,5-diformylfuran

Xiang

Liu

et al. 2013

Polym. Int.

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Polymerization of 2,5-diformylfuran with two primary amines was carried out in acetonitrile and ethanol at room temperature. The reaction was characterized using a combination of mass spectroscopy and NMR spectroscopy, which revealed the clean formation of the imine -CH N− functional group. Although some cyclic products were detected from mass spectroscopy, the ring size was limited to products that have the −CH N− group only in anti-geometry. The furan Schiff bases exhibit good thermal stability. While mass spectra evidenced oligomers of different lengths, cross-polarization magic angle spinning 13 C NMR spectra of the insoluble polymer revealed the linear structure as proposed.

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Section: Resultssupporting

confidence: 91%

Schiff base polymers derived from 2,5-diformylfuran

Xiang

Liu

et al. 2013

Polym. Int.

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“…Schiff bases are also capable of forming stable complexes by coordination to metal ions via their nitrogen donor atoms (Ebrahimipour et al, 2012). They are important for their photochromic properties and have applications in various fields such as the measurement and control of radiation intensities in imaging systems and in optical computers, electronics, optoelectronics and photonics (Iwan et al, 2007). ortho-Hydroxy Schiff base compounds such as the title compound can display two tautomeric forms, the enol-imine (OH) and keto-amine (NH) forms.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile

et al. 2020

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The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 2-aminobenzonitrile, and crystallizes in the orthorhombic space group Pbca. The phenol ring is inclined to the benzonitrile ring by 25.65 (3)°. The configuration about the C=N bond is E, stabilized by a strong intramolecular O—H...N hydrogen bond that forms an S(6) ring motif. In the crystal, C—H...O and C—H...N interactions lead to the formation of sheets perpendicular to the a axis. C—H...π interactions, forming polymeric chains along the a-axis direction, connect these sheets into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H...H and C...H/H...C interactions. The density functional theory (DFT) optimized structure at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO–LUMO energy gap is given.

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“…Moreover, Schiff base ligands are potentially capable of forming stable complexes by coordination of metal ions with their nitrogen atoms as donors (Ebrahimipour et al, 2012). They are important for their photochromic properties and have applications in various fields such as the measurement and control of radiation intensities in imaging systems, optical computers, electronics, optoelectronics and photonics (Iwan et al, 2007). The present work is a part of an ongoing structural study of Schiff bases and their utilization in the synthesis of quinoxaline derivatives (Faizi et al, 2018), fluorescence sensors (Faizi et al, 2016;Mukherjee et al, 2018;Kumar et al, 2017Kumar et al, , 2018 and non-linear optical properties (Faizi et al, 2020).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

et al. 2020

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The title compound, C15H14ClNO, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 3-chloro-4-methylaniline, and crystallizes in the monoclinic space group P21/c. The 3-chlorobenzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is E and an intramolecular O—H...N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H...H (43.8%) and C...H/H...C (26.7%) interactions. The density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO–LUMO energy gap is provided.

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Similarities and differences between azomethines and ketimines: Synthesis, materials characterization and structure of novel imines compounds

Cited by 20 publications

References 22 publications

Schiff base polymers derived from 2,5-diformylfuran

Schiff base polymers derived from 2,5-diformylfuran

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

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