5-Diethylamino-2-[(<i>E</i>)-(2,4-dimethoxyphenyl)iminomethyl]phenol

Kantar, Esen Nur; Köysal, Yavuz; Gümüş, Sümeyye; Ağar, Erbil; Soylu, Mustafa Serkan

doi:10.1107/s160053681201882x

Cited by 4 publications

(2 citation statements)

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“…The C13 = N1 and the C15-O1 bond distances are 1.288(3) Å and 1.323(3)Å, respectively. The obtained bond distances and angles are in expected normal ranges, and are consistent with our related structures [4][5][6].…”

Section: Discussionsupporting

confidence: 73%

Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C₁₉H₁₄N₂O₄

Köysal

Bülbül

Kantar

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 917436The asymmetric unit of the title crystal structure is shown in the gure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound (E)-4-nitro-2-((2-phenoxyphenylimino) methyl)phenol was prepared by re ux of a solution containing 2-hydroxy-5-nitrobenzaldehyde (0.157 g, 1.0 mmol) in 20 mL ethanol and a solution containing

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Section: Discussionsupporting

confidence: 73%

Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C₁₉H₁₄N₂O₄

Köysal

Bülbül

Kantar

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Schiff bases have extensively been structurally characterized, − but only a limited amount of studies have investigate the relationship between supramolecular motifs and nature/position of different substituents on a molecular framework. , …”

Section: Introductionmentioning

confidence: 99%

Structural Investigation of Substituent Effect on Hydrogen Bonding in (S)-Phenylglycine Amide Benzaldimines

George

Norberg

Leyssens

2015

Crystal Growth & Design

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A detailed structural analysis of 23 new crystal structures of (S)-phenylglycine amide benzaldimines with various substituents (CH3, Ph, OCH3, F, Cl, Br, NO2) on the benzylidene is performed in this contribution. These compounds belong to the highly studied family of Schiff bases. Etter’s nomenclature and Hirshfeld surfaces are used to describe respectively the strong hydrogen bonds and the secondary interactions existing in these compounds. Surprisingly, all 23 obtained structures can be sorted into five types according to their hydrogen bonding motifs. The potential interplay of steric and electronic effects of the substituents on the resulting bonding patterns, conformational features and packing was investigated. Our analysis revealed that neither mesomeric/inductive factors of halogens nor π–π stacking, C–H···π, and other hydrophobic interactions affect the structural outcome. The type affiliation is rather due to the interplay of three parameters: (1) the number of strong hydrogen bonds forming the motif (thermodynamic factor), (2) the ease with which the motif is formed (kinetic factor), and (3) the capacity of the motif to accommodate substituents on the different positions (steric factor). It was thus possible to suggest a stability ranking of the five structural types and to identify stable forms when polymorphism was encountered.

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4-Methoxy-2-{(E)-[(thiophen-2-yl)methylimino]methyl}phenol

et al. 2012

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.005 Å; R factor = 0.047; wR factor = 0.109; data-to-parameter ratio = 11.4.The title Schiff base, C 13 H 13 NO 2 S, adopts the phenol-imine tautomeric form and reveals an intramolecular O-HÁ Á ÁN hydrogen bond involving the hydroxy group and the imino N atom, forming an S(6) ring. The molecule is highly twisted with respect to the central imine group, which is reflected in the dihedral angle of 67.83 (10) formed by the thienyl and phenol rings. The crystal packing is characterized by weak C-HÁ Á ÁO and C-HÁ Á Á interactions. Related literatureSchiff bases of salicylaldehyde may exhibit thermochromism or photochromism, depending on the planarity or nonplanarity, respectively, of the molecule, see

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5-Diethylamino-2-[(E)-(2,4-dimethoxyphenyl)iminomethyl]phenol

Cited by 4 publications

References 5 publications

Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C₁₉H₁₄N₂O₄

Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C₁₉H₁₄N₂O₄

Structural Investigation of Substituent Effect on Hydrogen Bonding in (S)-Phenylglycine Amide Benzaldimines

4-Methoxy-2-{(E)-[(thiophen-2-yl)methylimino]methyl}phenol

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5-Diethylamino-2-[(E)-(2,4-dimethoxyphenyl)iminomethyl]phenol

Cited by 4 publications

References 5 publications

Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C19H14N2O4

Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C19H14N2O4

Structural Investigation of Substituent Effect on Hydrogen Bonding in (S)-Phenylglycine Amide Benzaldimines

4-Methoxy-2-{(E)-[(thiophen-2-yl)methylimino]methyl}phenol

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Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C₁₉H₁₄N₂O₄

Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C₁₉H₁₄N₂O₄