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3-[(E)-(4-Ethylphenyl)iminomethyl]benzene-1,2-diol
(Acta Crystallographica Section E, 2009) Keleşoğlu, Zeynep; Büyükgüngör, Orhan; Albayrak, Çiğdem; Odabaşoğlu, Mustafa
The title compound, C15H15NO2, adopts the enol-imine tautomeric form. The dihedral angle between the two benzene rings is 48.1 (1)°. Intramolecular O-H...N and O-H...O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. In the crystal, molecules are linked into centrosymmetric R22(10) dimers via pairs of O-H...O hydrogen bonds and the dimers may interact through very weak by [pi]-[pi] interactions [centroid-centroid distance = 4.150 (1) Å]. The ethyl group is disordered over two orientations, with occupancies of 0.587 (11) and 0.413 (11).
5-Diethylamino-2-[(E)-(4-ethoxyphenyl)iminomethyl]phenol
(Acta Crystallographica Section E, 2011) Soydemir, Erkan; Büyükgüngör, Orhan; Albayrak, Çiğdem; Odabaşoğlu, Mustafa
The title compound, C19H24N2O2, adopts the phenol-imine tautomeric form. An intramolecular O-H...N hydrogen bond results in the formation of a six-membered ring. The aromatic rings are oriented at a dihedral angle of 17.33 (16)°. Intermolecular C-H...[pi] interactions occur in the crystal.
Crystal Structure of (E)-3-[(4-Ethylphenylimino) methyl]benzene-1,2-diol and (E)-3-[(4-Butylphenyl imino)methyl]benzene-1,2-diol
(25th European Crystallographic Meeting, 2009) Keleşoğlu, Zeynep; Koşar, Başak; Albayrak, Çiğdem; Odabaşoğlu, Mustafa; Büyükgüngör, Orhan
[Abstract Not Available]
(E )-2-[(4-Fluorophenyl)iminomethyl]-5-methoxyphenol
(Acta Crystallographica Section E, 2010) Albayrak, Çiğdem; Özek, Arzu; Koşar, Başak; Odabaşoğlu, Mustafa; Büyükgüngör, Orhan
[Abstract Not Available]
(E )-5-Methoxy-2-(o-tolyliminomethyl)phenol
(Acta Crystallographica Section E, 2009) Albayrak, Çiğdem; Koşar, Başak; Özek, Arzu; Odabaşoğlu, Mustafa; Büyükgüngör, Orhan
[Abstract Not Available]
(E)-3-[(3-(Trifluoromethyl)phenylimino)methyl] benzene-1,2-diol: X-ray and DFT calculated structures
(2010) Koşar, Başak; Albayrak, Çiğdem; Odabaşoğlu, Mustafa; Büyükgüngör, Orhan
The crystal structure of (E)-3-[(3-(Trifluoromethyl)phenylimino)-methyl]benzene-1,2-diol was determined using X-ray diffraction and the molecular structure was investigated with density functional theory (DFT). The X-ray study showed that the title compound has a strong intramolecular O-H. . . N hydrogen bond and 3-dimensional crystal networks are primarily determined by O-H. . .O intermolecular hydrogen bonds and weak van der Waals interactions. The strong O-H. . .N bond is evidence of the preference for the phenol-imine tautomeric form in the solid state. Optimized molecular geometry was calculated with DFT at the B3LYP/6-31G(d,p) level. The results from both experiment and theoretical calculations for the title compound are compared with each other in this study.
(E)-3-[(3-(Trifluoromethyl)phenylimino)methyl]benzene-1,2-diol: X-ray and DFT calculated structures
(Turkish Journal of Chemistry, 2010) Koşar, Başak; Albayrak, Çiğdem; Odabaşoğlu, Mustafa; Büyükgüngör, Orhan
The crystal structure of (E)-3-[(3-(Trifluoromethyl)phenylimino)-methyl]benzene-1,2-diol was determined using X-ray diffraction and the molecular structure was investigated with density functional theory (DFT). The X-ray study showed that the title compound has a strong intramolecular O-H. . . N hydrogen bond and 3-dimensional crystal networks are primarily determined by O-H. . .O intermolecular hydrogen bonds and weak van der Waals interactions. The strong O-H. . .N bond is evidence of the preference for the phenol-imine tautomeric form in the solid state. Optimized molecular geometry was calculated with DFT at the B3LYP/6-31G(d,p) level. The results from both experiment and theoretical calculations for the title compound are compared with each other in this study.
(E)-3-[(3-Bromophenyl)iminomethyl]benzene-1,2-diol: a combined X-ray and computational structural study
(Acta Crystallographica Section E, 2009) Keleşoğlu, Zeynep; Büyükgüngör, Orhan; Albayrak, Çiğdem; Odabaşoğlu, Mustafa
The title compound, C13H10BrNO2, exists as an enol-imine form in the crystal and adopts an E configuration with respect to the C=N double bond. The molecule is close to planar, with a dihedral angle of 6.88 (14)° between the aromatic rings. Intramolecular O-H...N and O-H...O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. The crystal structure is stabilized by intermolecular O-H...O hydrogen-bond interactions, forming R22(10) and R22(20) chains along [100]. ab initio Hartree-Fock (HF), density-functional theory (DFT) and semi-empirical (AM1 and PM3) calculations and full-geometry optimizations were also performed. Although there are some discrepancies between the experimental and calculated parameters, caused presumably by the O-H...O hydrogen-bond interactions, there is an acceptable general agreement between them.
(E)-3-[(4-Butylphenyl)iminomethyl]benzene-1,2-diol
(Acta Crystallographica Section E, 2009) Keleşoğlu, Zeynep; Büyükgüngör, Orhan; Albayrak, Çiğdem; Odabaşoğlu, Mustafa
The title compound, C17H19NO2, exists as an enol-imine tautomer. The dihedral angle between the two benzene rings is 4.6 (2)°. The molecular structure is stabilized by intramolecular O-H...O and O-H...N hydrogen bonds which generate S(5) and S(6) ring motifs, respectively. In the crystal, molecules are linked into centrosymmetric dimers by pairs of O-H...O hydrogen bonds. In addition, C-H...[pi] interactions involving both benzene rings are observed.
(E)-4-Methoxy-2-(o-tolyliminomethyl)phenol
(Acta Crystallographica Section E, 2009) Özek, Arzu; Büyükgüngör, Orhan; Albayrak, Çiğdem; Odabaşoğlu, Mustafa
In the molecule of the title compound, C15H15NO2, the aromatic rings are oriented at a dihedral angle of 15.46 (6)°. An intramolecular O-H...N hydrogen bond results in the formation of a nearly planar six-membered ring [maximum deviation of 0.035 (5) Å for the N atom] which is almost coplanar with the adjacent ring, making a dihedral angle of 0.8 (3)°. The title organic molecule is a phenol-imine tautomer, as evidenced by the C-O, C-N and C-C bond lengths. Molecules are linked by intermolecular C-H...O hydrogen bonds that generate a C(5) chain. C-H...[pi] and [pi]-[pi] interactions exist in the structure. The [pi]-[pi] interaction occurs between the phenol ring and its symmetry equivalent at (1 - x, 1 - y, -z), with a centroid-centroid distance of 3.727 (7) Å and a plane-to-plane separation of 3.383 (5) Å, resulting in an offset angle of 24.82 (1)°.
(E)-4-Methoxy-2-[3-(trifluoromethyl)phenyliminomethyl]phenol
(Acta Crystallographica Section E, 2009) Keleşoğlu, Zeynep; Büyükgüngör, Orhan; Albayrak, Çiğdem; Odabaşoğlu, Mustafa
The title compound, C15H12F3NO2, adopts the phenol-imine tautomeric form, with the H atom attached to oxygen rather than to nitrogen. There are two independent molecules aligned nearly parallel in the asymmetric unit with their trifloramethyl groups pointing in opposite directions. The dihedral angles between the aromatic rings are 40.43 (1)° in the first molecule and 36.12 (1)° in the second. Strong intramolecular O-H...N hydrogen bonding generates S(6) ring motifs. Weak intermolecular C-H...O hydrogen bonds link the independent molecules separately into sheets normal to [010]. In addition, C-H...[pi] interactions are also observed. The F atoms of the trifluoromethyl groups are disordered over two sets of sites with refined site occupancies of 0.59 (2)/0.41 (2) and 0.62 (3)/0.38 (3), respectively.
Electrochemical and Spectroscopic Study of 4-(Phenyldiazenyl)-2-{[tris- (hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one. Mechanism of the Azo and Imine Electroreduction
(Journal of the Brazilian Chemical Society, 2005) Çakır, Semiha; Biçer, Ender; Odabaşoğlu, Mustafa; Albayrak, Çiğdem
O composto 4-(fenildiazenil)-2-{[tris(hidroximetil)metil]aminometileno}ciclohexa-3,5-dien- 1(2H)-ona foi sintetizado e caracterizado por análise elementar, espectroscopia infravermelho, ressonância magnética nuclear, espectro eletrônico e voltametria cíclica. O equilíbrio tautomérico do 4-(fenildiazenil)-2-{[tris(hidroximetil)metil]aminometileno} ciclohexa-3,5-dien-1(2H)-ona emdimeteilsulfóxido deuterado é comprovado por dados de 1H RMN. A natureza do processo eletroquímico do 4-(fenildiazenil)-2-{[tris(hidroximetil)metil]aminometileno} ciclohexa-3,5-dien-1(2H)-ona em solução tampão de Britton-Robinson (pH 2-9) foi estudada com o eletrodo gotejante de mercúrio utilizando voltametria de onda quadrada, onda quadrada adsortiva e voltametria cíclica. Os parâmetros eletroquímicos do composto (Ip/Ep, Ip/v, Ip/pH, Ip/t acc) foram determinados. Newly synthesized 4-(phenyldiazenyl)-2-{[tris(hydroxymethyl)methyl]aminomethylene} cyclohexa-3,5-dien-1(2H)-one was characterized by elemental analysis, FT-IR, NMR, electronic spectra, voltammetry. Tautomeric equilibrium of 4-(phenyldiazenyl)-2-{[tris(hydroxymethyl) methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one in DMSO dis supported by 1H NMR data. The nature of electrochemical process of 4-(phenyldiazenyl)-2-{[tris(hydroxymethyl) methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one in Britton-Robinson buffer (pH 2–9) was studied on the HMDE by square-wave (SWV), adsorptive stripping square-wave (AdSWV) and cyclic voltammetry (CV). The electrochemical parameters (Ip/Ep,Ip/v,Ip/pH,Ip/tacc) of the compound were determined.
X-ray and computational structural study of (E)-2-(4-chlorophenyliminomethyl)-4-methoxyphenol
(Acta Crystallographica Section E, 2008) Özek, Arzu; Büyükgüngör, Orhan; Albayrak, Çiğdem; Odabaşoğlu, Mustafa
In the molecule of the title compound, C14H12ClNO2, the two aromatic rings are oriented at a dihedral angle of 5.92 (7)°. An intramolecular O-H...N hydrogen bond results in the formation of a nearly planar six-membered ring, which is oriented at dihedral angles of 1.55 (4) and 5.95 (4)° with respect to the phenol and chlorophenyl rings, respectively. In the crystal structure, weak intermolecular C-H...O hydrogen bonds link the molecules into a three-dimensional network.
X-ray crystal and computational structural study of (E)-2-[(2-chlorophenyl)iminomethyl]-4-methoxyphenol
(Acta Crystallographica Section E, 2008) Özek, Arzu; Büyükgüngör, Orhan; Albayrak, Çiğdem; Odabaşoğlu, Mustafa
In the molecule of the title compound, C14H12ClNO, the two aromatic rings are oriented at a dihedral angle of 12.28 (7)°. An intramolecular O-H...N hydrogen bond results in the formation of a nearly planar six-membered ring, which is oriented with respect to the aromatic rings at dihedral angles of 0.18 (5) and 12.10 (6)°. In the crystal structure, weak intermolecular C-H...O hydrogen bonds link the molecules into chains along the c axis. There is a C-H...[pi] contact between the methyl group and the chlorophenyl ring and a [pi]-[pi] contact between the two benzene rings [centroid-centroid distance = 3.866 (1) Å].
(Z)-6-[(5-Chloro-2-hydroxyanilino)methylene]-4-methoxycyclohexa-2,4-dienone 0.25-hydrate
(Acta Crystallographica Section E, 2009) Özek, Arzu; Büyükgüngör, Orhan; Albayrak, Çiğdem; Odabaşoğlu, Mustafa
The title compound, C14H12ClNO3·0.25H2O, exists in the keto-amine form, and the aromatic rings are oriented at a dihedral angle of 7.24 (7)°. Bifurcated intramolecular N-H...(O,O) hydrogen bonds result in the formation of planar six- and five-membered rings. In the crystal structure, intermolecular O-H...O and C-H...O hydrogen bonds link the molecules into chains. [pi]-[pi] contacts between benzene rings [centroid-centroid distance = 3.5065 (9) Å] may further stabilize the structure. There also exists a weak C-H...[pi] interaction.

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