Dimethyl 5-(3,4-dicyanophenoxy)isophthalate

Petek, Hande; Akdemir, Nesuhi; Ağar, Erbil; Gümrükçüoğlu, İsmail Erdem; Şenel, İsmet

doi:10.1107/s1600536806015108

Cited by 2 publications

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“…The IR spectra show a strong band at 2,220 cm -1 with a shoulder at 2,216 cm -1 , which are assigned to C:N stretching mode in meta and para positions, respectively. This band is peculiar to phenoxy phthalonitrile compounds in the 2,210-2,241 cm -1 region as in similar compounds [31][32][33][34][35][36]. Difference between nitrile stretching frequencies is related to chemical difference of the nitrile groups bonded to nonequivalent sites of the phthalonitrile ring.…”

Section: Resultsmentioning

confidence: 99%

Mesomeric effect on the structural and electronic properties of 4-(2-tert-butyl-4-methylphenoxy)phthalonitrile

2010

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The molecular and crystal structures of the title compound, C 19 H 18 N 2 O, were determined and characterized by single crystal X-ray diffraction and spectroscopic methods. Details of the molecular geometry imply that there is a mesomeric effect between the electron-withdrawing N atoms of nitrile substituents and electrondonating O atom. Formally, single central O-C ar bond lengths are considerably different from each other. O-C ar distance to phthalonitrile ring is shorter than the other O-C ar distance due to mesomeric effect under discussion. In addition to structural and spectral evidences, possible results from mesomerism of the compound were investigated by topological analysis on the electronic properties using quantum theory of atoms in molecules (QTAIM) approach. It is inferred from topological analysis that the nitrile group in para position has slightly stronger mesomeric effect than that in meta position due to diffusive double charge separation property during meta mesomerism of the compound. Mesomeric effect revealing itself by differences in delocalization indices between certain bonded atom pairs results in considerable decrease in aromaticity of phthalonitrile ring.

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Section: Resultsmentioning

confidence: 99%

Mesomeric effect on the structural and electronic properties of 4-(2-tert-butyl-4-methylphenoxy)phthalonitrile

2010

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Crystal structure and Hirshfeld surface analysis of diethyl 5-(2-cyanophenoxy)isophthalate

et al. 2020

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The title compound, C19H17NO5, obtained by ether bond formation between the reagents, crystallizes in the monoclinic space group P21/c. The compound is non-planar, subtending a dihedral angle of 82.38 (4)° between the plane of hydroxy isophthalate-based ester and that of the benzonitrile moiety. The molecule is bent at the ether linkage, with a Caryl—O—Caryl bond angle of 116.74 (11)°. In the crystal, molecules are linked by C—H...O hydrogen bonds and other weak interactions forming a supramolecular framework. A Hirshfeld surface analysis was performed to generate two-dimensional fingerprint plots, which reveal the type of interactions occurring in the vicinity of the molecule.

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Dimethyl 5-(3,4-dicyanophenoxy)isophthalate

Abstract: The crystal structure of the title compound, C18H12N2O5, is stabilized by intermolecular C—H⋯O and π–π interactions.

Cited by 2 publications

References 4 publications

Mesomeric effect on the structural and electronic properties of 4-(2-tert-butyl-4-methylphenoxy)phthalonitrile

Mesomeric effect on the structural and electronic properties of 4-(2-tert-butyl-4-methylphenoxy)phthalonitrile

Crystal structure and Hirshfeld surface analysis of diethyl 5-(2-cyanophenoxy)isophthalate

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Dimethyl 5-(3,4-dicyanophenoxy)isophthalate

Abstract: The crystal structure of the title compound, C18H12N2O5, is stabilized by inter­molecular C—H⋯O and π–π inter­actions.

Cited by 2 publications

References 4 publications

Mesomeric effect on the structural and electronic properties of 4-(2-tert-butyl-4-methylphenoxy)phthalonitrile

Mesomeric effect on the structural and electronic properties of 4-(2-tert-butyl-4-methylphenoxy)phthalonitrile

Crystal structure and Hirshfeld surface analysis of diethyl 5-(2-cyanophenoxy)isophthalate

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Abstract: The crystal structure of the title compound, C18H12N2O5, is stabilized by intermolecular C—H⋯O and π–π interactions.