(<i>E</i>)-<i>N</i>-[(2-Ethoxynaphthalen-1-yl)methylidene]-2-ethylaniline

Kargılı, Hakan; Macit, Mustafa; Alpaslan, Gökhan; Kazak, Canan; Erdönmez, Ahmet

doi:10.1107/s1600536812043097

Cited by 3 publications

(3 citation statements)

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“…In (I) ( Fig. 1), the C13═N1 bond distance of 1.262 (3) Å is shorter than the standart 1.28 Å value of C═N double bond, similar to the corresponding bond distance in (E)-N-[(2-ethoxynaphthalen-1-yl)methylidene]-2-ethylaniline [1.261 3Å; Kargılı et al,2012]. The dihedral angle between the naphthalene ring system and the benzene ring is 85.82 (7)°.…”

Section: Methodssupporting

confidence: 57%

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(E)-(2,5-Difluorobenzyl)[(2-ethoxynaphthalen-1-yl)methylidene]amine

et al. 2013

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Section: Methodssupporting

confidence: 57%

“…For structural studies of Schiff bases by our group, see: Gü l et al (2007); Kantar et al (2012); Kargılı et al (2012); Pekdemir et al (2012); Vesek et al (2012). For classification of hydrogenbonding patterns, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

(E)-(2,5-Difluorobenzyl)[(2-ethoxynaphthalen-1-yl)methylidene]amine

et al. 2013

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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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Synthesis, crystal structures, spectroscopic analysis and DFT calculations of 2-ethoxy-1-naphtaldehyde and (E)-N-((2-ethoxynaphthalen-1-yl)methylene)-3-methylaniline

Yıldırım

Macit

et al. 2016

Journal of Molecular Structure

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(E)-N-[(2-Ethoxynaphthalen-1-yl)methylidene]-2-ethylaniline

Abstract: In the title compound, C21H21NO, the dihedral angle between the naphthalene ring system and the benzene ring is 64.61 (6)°. The molecular structure is stabilized by an intramolecular C—H⋯N hydrogen bond.

Cited by 3 publications

References 6 publications

(E)-(2,5-Difluorobenzyl)[(2-ethoxynaphthalen-1-yl)methylidene]amine

(E)-(2,5-Difluorobenzyl)[(2-ethoxynaphthalen-1-yl)methylidene]amine

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

Synthesis, crystal structures, spectroscopic analysis and DFT calculations of 2-ethoxy-1-naphtaldehyde and (E)-N-((2-ethoxynaphthalen-1-yl)methylene)-3-methylaniline

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(E)-N-[(2-Ethoxynaphthalen-1-yl)methylidene]-2-ethylaniline

Abstract: In the title compound, C21H21NO, the dihedral angle between the naphthalene ring system and the benzene ring is 64.61 (6)°. The mol­ecular structure is stabilized by an intra­molecular C—H⋯N hydrogen bond.

Cited by 3 publications

References 6 publications

(E)-(2,5-Difluorobenzyl)[(2-ethoxynaphthalen-1-yl)methylidene]amine

(E)-(2,5-Difluorobenzyl)[(2-ethoxynaphthalen-1-yl)methylidene]amine

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

Synthesis, crystal structures, spectroscopic analysis and DFT calculations of 2-ethoxy-1-naphtaldehyde and (E)-N-((2-ethoxynaphthalen-1-yl)methylene)-3-methylaniline

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Abstract: In the title compound, C21H21NO, the dihedral angle between the naphthalene ring system and the benzene ring is 64.61 (6)°. The molecular structure is stabilized by an intramolecular C—H⋯N hydrogen bond.