Synthesis, spectroscopic studies and crystal structure of (E)-2-(2,4-dihydroxybenzylidene)thiosemicarbazone and (E)-2-[(1H-indol-3-yl)methylene]thiosemicarbazone

Yıldız, Mustafa; Ünver, Hüseyin; Erdener, Diğdem; Kiraz, Aşkın; Ískeleli, Nazan Ocak

doi:10.1016/j.molstruc.2008.09.008

Cited by 28 publications

(2 citation statements)

References 42 publications

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“…This confirms the existence of the compound in the thioamido form in the solid state, similar to the situation observed in some related compounds, viz. (E)-2-(2,4-dihydroxybenzylidene)thiosemicarbazone and (E)-2-[(1H-indol-3-yl)methylene]thiosemicarbazone (Yıldız et al, 2009). The C1-N7 bond distance is 1.278 (3) Å , close to that of a C N double bond, confirming the azomethine bond formation, again similar to the situation observed in related compounds, viz.…”

Section: Structural Commentarysupporting

confidence: 77%

Crystal structure and Hirshfeld surface analysis of (E)-2-(5-bromo-2-hydroxybenzylidene)hydrazinecarbothioamide dimethyl sulfoxide monosolvate

et al. 2018

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The molecule of the title Schiff base, C 8 H 8 BrN 3 OSÁC 2 H 6 OS, which crystallizes as a dimethyl sulfoxide (DMSO) monosolvate, displays an E configuration with respect to the C N bond, with a dihedral angle of 14.54 (11) between the benzene ring and the mean plane of the N-N-C(N) S unit. In the crystal, molecules are linked by N-HÁ Á ÁO hydrogen bonds, forming chains propagating along the b-axis direction. Within the chains there are R 2 3 (11) ring motifs, which are reinforced by C-HÁ Á ÁO DMSO hydrogen bonds enclosing secondary R 1 2 (6) and R 2 3 (9) loops. The chains are linked by O-H hydroxyl Á Á ÁS hydrogen bonds, forming layers parallel to (011). Inversion-related layers are linked by short BrÁ Á ÁBr interactions [3.5585 (5) Å ], forming slabs parallel to (011). The intermolecular interactions have been investigated using Hirshfeld surface studies and two-dimensional fingerprint plots. The crystal structure of the unsolvated form of the title compound has been reported previously [Kargar et al. (2010). Acta Cryst. E66, o2999], and its solid-state structure is compared with that of the title solvated form.

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Section: Structural Commentarysupporting

confidence: 77%

Crystal structure and Hirshfeld surface analysis of (E)-2-(5-bromo-2-hydroxybenzylidene)hydrazinecarbothioamide dimethyl sulfoxide monosolvate

et al. 2018

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“…7). The stretching vibration bands of v(C = N) and v(C = S) in free L appeared at 1622 cm −1 and 1252 cm −1 , respectively [40]. The intensity of these bands were greatly decreased after L coordinate with Zn 2+ , indicating the participation of the azomethine N and thiocarbonyl S atom in the coordination of the metal ion.…”

Section: Binding Mode Of L With Zn 2+mentioning

confidence: 96%

A New Thiosemicarbazone-Based Fluorescence “Turn-on” Sensor for Zn2+ Recognition with a Large Stokes Shift and its Application in Live Cell Imaging

et al. 2016

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Selective fluorescence turn on Zn(2+) sensor with long-wavelength emission and a large Stokes shift is highly desirable in Zn(2+) sensing area. We reported herein the synthesis and Zn(2+) recognition properties of a new thiosemicarbazone-based fluorescent sensor L. L displays high selectivity and sensitivity toward Zn(2+) over other metal ions in DMSO-H2O (1:1, v/v, HEPES 10 mM, pH = 7.4) solution with a long-wavelength emission at 572 nm and a large Stokes shift of 222 nm. Confocal fluorescence microscopy experiments demonstrate that L is cell-permeable and capable of monitoring intracellular Zn(2+). Graphical Abstract We report a new thiosemicarbazone-based fluorescent sensor (L) for selective recognition of Zn(2+) with a long wavelength emission and a large Stokes shift.

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Synthesis, spectroscopic characterization, crystal structures, and theoretical studies of (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone

et al. 2010

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Two thiosemicarbazones, (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone (24-MBTSC (1)) and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone (25-MBTSC (2)), derived from 2,4-dimethoxybenzaldehyde and 2,5-dimethoxybenzaldehyde, respectively, with thiosemicarbazide have been synthesized and their structures were characterized by elemental analyses, FT-IR, 1 H NMR spectroscopy, and X-ray single-crystal diffraction analysis. Molecular orbital calculations have been carried out for 1 and 2 by using an ab initio method (HF) and also density functional method (B3LYP) at 6-31G basis set. Compound 1 crystallizes in the monoclinic system, space group P2 1 /c, with a = 8.1342(5) Å , b = 18.1406(10) Å , c = 8.2847(6) Å , b = 109.7258(17)°, V = 1150.75(12) Å 3 , and Z = 4, whereas compound 2 crystallizes in the orthorhombic system, space group Pbca, with a = 11.0868(6) Å , b = 13.1332(6) Å , c = 15.9006(8) Å , V = 2315.2(2) Å 3 , and Z = 8. The compounds 1 and 2 displays a trans-configuration about the C=N double bond.

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Synthesis, spectroscopic studies and crystal structure of (E)-2-(2,4-dihydroxybenzylidene)thiosemicarbazone and (E)-2-[(1H-indol-3-yl)methylene]thiosemicarbazone

Cited by 28 publications

References 42 publications

Crystal structure and Hirshfeld surface analysis of (E)-2-(5-bromo-2-hydroxybenzylidene)hydrazinecarbothioamide dimethyl sulfoxide monosolvate

Crystal structure and Hirshfeld surface analysis of (E)-2-(5-bromo-2-hydroxybenzylidene)hydrazinecarbothioamide dimethyl sulfoxide monosolvate

A New Thiosemicarbazone-Based Fluorescence “Turn-on” Sensor for Zn2+ Recognition with a Large Stokes Shift and its Application in Live Cell Imaging

Synthesis, spectroscopic characterization, crystal structures, and theoretical studies of (E)-2-(2,4-dimethoxybenzylidene)thiosemicarbazone and (E)-2-(2,5-dimethoxybenzylidene)thiosemicarbazone

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