(<i>Z</i>)-3-({[3-Methoxy-5-(trifluoromethyl)phenyl]imino}methyl)benzene-1,2-diol

Kanmazalp, Sibel Demi̇r; Doğan, Onur Erman; Dege, Necmi; Ağar, Erbil; Bülbül, Hakan; Golenya, Irina A.

doi:10.1107/s2056989019003220

Cited by 3 publications

(4 citation statements)

References 20 publications

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“…di is the distance from the inner surface of the nearest atom. In addition, the white, blue, and red colors represented on the Hirshfeld surface in the dnorm map indicate that the interaction distances between atoms are equal, longer, or shorter than the Van der Waals surface [21,22]. Figure 3 (2.5%) in percentile order.…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

Crystal structure and computational studies of N-((2-ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline

2021

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The Schiff base compound, N-((2-ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline, has been synthesized and characterized by X-ray diffraction method. The title compound, C19H16FNO, crystallizes in triclinic, space group P-1 (no. 2), a = 10.6343(9) Å, b = 11.4720(10) Å, c = 13.8297(13) Å, α = 102.466(7)°, β = 104.763(7)°, γ = 98.972(7)°, V = 1552.7(2) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.086 mm-1, Dcalc = 1.255 g/cm3, 24355 reflections measured (3.16° ≤ 2Θ ≤ 51°), 5779 unique (Rint = 0.0794, Rsigma = 0.0696) which were used in all calculations. The final R1 was 0.0373 (I > 2σ(I)) and wR2 was 0.0763 (all data). The title compound contains two molecules with a similar structure in the asymmetric unit cell. The packing of the crystal structure is determined by weak C–H···F and C-H···N intermolecular hydrogen bonds. The contributions of these weak interactions in the crystal structure were calculated by the Hirshfeld surfaces and examined by the intermolecular interactions within the structure. The existence, nature and percentage contribution of different intermolecular interactions H···H, C···H, N···H, and F···H were determined using Hirshfeld surface analysis and fingerprint plots.

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Section: Hirshfeld Surface Analysismentioning

confidence: 99%

Crystal structure and computational studies of N-((2-ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline

2021

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“…These benefits, together with their higher stability and the wide range of structural forms they take, elucidate their importance as therapeutic drugs, with their aromatic and hydrophilic properties enhancing the biological impact . They are also utilized in a broad variety of industrial practices, covering the fabrication of dyes, paints, and pigments …”

Section: Introductionmentioning

confidence: 99%

“…6 They are also utilized in a broad variety of industrial practices, covering the fabrication of dyes, paints, and pigments. 7 It is quite intriguing how a Schiff base chelates with transition metal ions. A Schiff base chelates with the metal ion via the nitrogen atom of the azomethine linkage.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterizations, Hirshfeld Surface Analysis, DFT, and NLO Study of a Schiff Base Derived from Trifluoromethyl Amine

Tahir,

Ashfaq,

Munawar

et al. 2024

ACS Omega

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We synthesized an imine-based (Schiff base) crystalline organic chromophore, i.e., (E)-2-ethoxy-6-(((3-(trifluoromethyl)phenyl)imino)methyl)phenol (ETPMP), and explored its nonlinear optical (NLO) properties. The crystalline structure of ETPMP was determined by the XRD technique and equated with the associated structures utilizing a Cambridge Structural Database search. The supramolecular assembly of ETPMP was investigated regarding intermolecular interactions and short contacts by Hirshfeld surface analysis. Void analysis was performed to check the mechanical response of the crystal. Supramolecular assembly was further inspected by interaction energy calculations that were performed with the B3LYP/6-31G(d,p) functional. Besides this, the NLO properties of ETPMP and other already reported crystal TFMOS were explored utilizing the M06/6-31G(d,p) functional of the DFT approach. An excellent agreement was observed between XRD and DFT results of geometric parameters of the above-mentioned crystals. Narrow band gap along with bathochromic shift (3.489 eV and 317.225 nm, respectively) were investigated in TFMOS than that of ETPMP. Owing to these unique properties, TFMOS possesses higher linear (⟨a⟩ = 3.835 × 10 −23 esu) and nonlinear (γ tot. = 1.346 × 10 −34 esu) response as compared to ETPMP. The outcomes explicitly show the higher nonlinearity in TFMOS, highlighting its importance in potential NLO applications.

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Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol

et al. 2021

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The title compound, C13H14N4O, was developed using the reaction of salicylaldehyde and 3-amino-5-cyclobutyl-1,2,4-triazole in ethanol under microwave irradiation. This eco-friendly microwave-promoted method proved to be efficient in the synthesis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol in good yields and purity. The title compound is a Schiff base that exists in the phenol–imine tautomeric form and adopts an E configuration. The three independent molecules in the asymmetric unit (A, B and C) are not planar, the cyclobutyl and the phenol-imine rings are twisted to each other making a dihedral angle of 67.8 (4)° in molecule A, 69.1 (2)° in molecule B and 89.1 (2)° in molecule C. In each molecule an intramolecular O—H...N hydrogen bond is present, forming an S(6) ring motif. A Hirshfeld surface analysis was performed to investigate the contributions of the different intermolecular contacts within the supramolecular structure. The major interactions are H...H (53%), C...H (19%) and N...H (17%) for molecule A, H...H (50%), N...H (20%) and C...H (20%) for molecule B and H...H (57%), C...H (14%) and N...H (13%) for molecule C.

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(Z)-3-({[3-Methoxy-5-(trifluoromethyl)phenyl]imino}methyl)benzene-1,2-diol

Cited by 3 publications

References 20 publications

Crystal structure and computational studies of N-((2-ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline

Crystal structure and computational studies of N-((2-ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline

Synthesis, Characterizations, Hirshfeld Surface Analysis, DFT, and NLO Study of a Schiff Base Derived from Trifluoromethyl Amine

Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol

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