Crystal structure and Hirshfield surface analysis of 4-phenyl-3-(thiophen-3-ylmethyl)-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione

Quoc, Trung Vu; Ngoc, Linh Nguyen; Ba, Dai Do; Pham, Chien Thang; Huy, Hung Nguyen; Meervelt, Luc Van

doi:10.1107/s2056989018007193

Cited by 6 publications

(2 citation statements)

References 14 publications

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“…The short distance C8=N2 [1.2972 ( 17) Å] is compatible with double-bond character. These values are in accordance with those reported for compound with 1,2,4triazolemoiety [49]. The distance C7=S1 of 1.6689 (13) Å, compatible with double-bond character [50] indicates that the compound exists only in its thione form.…”

Section: X-ray Structures Determinationsupporting

confidence: 91%

Syntheses and Antioxidant Activity of 1-Isonicotinoyl-4-phenylthiosemicarbazide and Crystal Structures of N-Phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine Hydrochloride and 4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione derived from 1 Isonicotinoyl-4-phenylthiosemicarbazide

Faye

Mbow

Gaye

et al. 2022

EJCS

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The title compound C13H12N4OS (I) is synthetized from isonicotinic hydrazide and isothiocynate. Compounds C13H11N4OCl (II) and C13H10N4S (III) where obtained upon reaction of (I) with Fe(II) or Mn(II) salts. Compound (II) is heterocyclic 1,3,4-oxadiazole while compound (III) is heterocyclic 1,2,4-triazole. The 1,3,4-oxadiazol derivative is almost planar with dihedral angle of 2.66 (8) and 5.14 (8)° between 1,3,4-oxadiazole ring and phenyl and pyridinium rings respectively; the dihedral angle between the phenyl and pyridinium rings is 3.92 (8)°. The 1,2,4-triazole derivative is non-planar. The phenyl and pyridyl rings form dihedral angles of 58.35 (5) and 58.33 (5)°, respectively, with the 1,2,4-triazole ring; the dihedral angle between the phenyl and pyridyl rings is 36.85 (4)°. In the compound (II) intramolecular hydrogen bonds of type N—H···Cl, C—H···N and C—H···Cl resulting in S(6) ring stabilize the structure. Intermolecular hydrogen bonds of type N—H···N, C—H···N, C—4···Cl link the molecule thus forming a three-dimensional network. In the structure of compound (III), intermolecular hydrogen bonds of type N—H···N, C—H···N, C—H···S1,link the monomer in a three-dimensional network.

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Section: X-ray Structures Determinationsupporting

confidence: 91%

Syntheses and Antioxidant Activity of 1-Isonicotinoyl-4-phenylthiosemicarbazide and Crystal Structures of N-Phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine Hydrochloride and 4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione derived from 1 Isonicotinoyl-4-phenylthiosemicarbazide

Faye

Mbow

Gaye

et al. 2022

EJCS

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“…As a continuation of our research on the chemical and physical properties of novel polythiophenes (Nguyen et al, 2016; Vu et al, 2016), some new thiophene monomers have ISSN 2056-9890 been prepared (Vu et al, 2017(Vu et al, , 2018(Vu et al, , 2019Nguyen et al, 2017). In this study, the synthesis and crystal structure of diethyl 2,6dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate are presented together with a Hirshfeld surface analysis and non-covalent interaction plots.…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis, crystal structure and Hirshfeld surface analysis of diethyl 2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

et al. 2019

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Synthesis and characterization of novel poly[4‐phenyl‐3‐(thiophen‐3‐ylmethyl)‐1H‐1,2,4‐triazole‐5(4H)‐thione]

Trung

Linh²,

Chinh

et al. 2019

Vietnam Journal of Chemistry

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By the oxidative coupling polymerization, a new polythiophene containing 1,2,4‐triazole heterocyclic group was synthesized in chloroform solvent using iron(III) chloride as an oxidant catalyst. Analyses of infrared (IR) and ultraviolet–visible (UV‐Vis) spectra confirmed that the polymerization reaction took place and the absorption band at 469 nm characterized for π–π* transition in the conjugated polymer. Morphology and surface properties of the polymer were studied by field emission scanning electron microscopy (FESEM). Polymer had relatively uniform size distribution. Based on thermal gravimetry analysis (TGA), polymer is without impurities and has an adequate thermal stability in air atmosphere when completely decomposed at 500 oC. The polymer exhibited fluorescence emissions at 596 nm corresponding to the conjugated chain in polymer. Polymer exhibited a good electrical conductivity in the undoped state (around 1.37E–7 S.cm‐1 at 1 MHz).

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Crystal structure and Hirshfield surface analysis of 4-phenyl-3-(thiophen-3-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione

Abstract: The synthesis and crystal structure of a new thiophene monomer containing a 1,2,4-triazole-5-thione ring are reported. The thiophene and 1,2,4-triazole rings are inclined to each other by 79.70 (9)°.

Cited by 6 publications

References 14 publications

Syntheses and Antioxidant Activity of 1-Isonicotinoyl-4-phenylthiosemicarbazide and Crystal Structures of N-Phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine Hydrochloride and 4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione derived from 1 Isonicotinoyl-4-phenylthiosemicarbazide

Syntheses and Antioxidant Activity of 1-Isonicotinoyl-4-phenylthiosemicarbazide and Crystal Structures of N-Phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine Hydrochloride and 4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione derived from 1 Isonicotinoyl-4-phenylthiosemicarbazide

Synthesis, crystal structure and Hirshfeld surface analysis of diethyl 2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Synthesis and characterization of novel poly[4‐phenyl‐3‐(thiophen‐3‐ylmethyl)‐1H‐1,2,4‐triazole‐5(4H)‐thione]

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Crystal structure and Hirshfield surface analysis of 4-phenyl-3-(thiophen-3-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione

Abstract: The synthesis and crystal structure of a new thio­phene monomer containing a 1,2,4-triazole-5-thione ring are reported. The thio­phene and 1,2,4-triazole rings are inclined to each other by 79.70 (9)°.

Cited by 6 publications

References 14 publications

Syntheses and Antioxidant Activity of 1-Isonicotinoyl-4-phenylthiosemicarbazide and Crystal Structures of N-Phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine Hydrochloride and 4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione derived from 1 Isonicotinoyl-4-phenylthiosemicarbazide

Syntheses and Antioxidant Activity of 1-Isonicotinoyl-4-phenylthiosemicarbazide and Crystal Structures of N-Phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine Hydrochloride and 4-Phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione derived from 1 Isonicotinoyl-4-phenylthiosemicarbazide

Synthesis, crystal structure and Hirshfeld surface analysis of diethyl 2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Synthesis and characterization of novel poly[4‐phenyl‐3‐(thiophen‐3‐ylmethyl)‐1H‐1,2,4‐triazole‐5(4H)‐thione]

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Abstract: The synthesis and crystal structure of a new thiophene monomer containing a 1,2,4-triazole-5-thione ring are reported. The thiophene and 1,2,4-triazole rings are inclined to each other by 79.70 (9)°.