Novel compounds of 4-amino-1,2,4-triazole with dicarboxylic acids – crystal structures, vibrational spectra and non-linear optical properties

Matulková, Irena; Němec, Ivan; Teubner, Karel; Němec, Petr; Mička, Zdeněk

doi:10.1016/j.molstruc.2007.03.007

Cited by 85 publications

(65 citation statements)

References 41 publications

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“…m NH (3322-3180 cm -1 ), m C=O (1634-1676 cm -1 ), and d NH (1600-1500 cm -1 ). Here, both m NH and m C=O bands are shifted to lower frequency because of hydrogen-bond formation, which is consistent with earlier studies [25][26][27].…”

Section: Ir Spectroscopysupporting

confidence: 92%

Self-assembly of amides of endo-3-(3-methylthio-1H-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid directed by N-amide substituents

et al. 2010

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The condensation of endo-S-methyl-N 0 -(bicyclo[2.2.1]hept-5-ene-2,3-dicarbonyl) isothiosemicarbazide with 12 primary amines was investigated. The molecular structure of all new products (3a-3l) was confirmed by spectroscopic methods, including 1D/2D NMR, IR spectroscopy and mass spectrometry, and an X-ray crystallography of three selected representative amide crystals. The 2,3-disubstitution of norbornene (endo-bicyclo[2.2.1]hept-5-ene) unit stabilizes overall cisoid orientation of substituents. Spectroscopic and structural analyses indicate that for the series of 12 derivatives the rigid molecular part is endo-bicyclo[2.2.1]hept-5-ene-2-carboxamide fragment. The specific orientation of the 3-(methylthio)-1H-1,2, 4-triazole unit, second substituent to the norbornene skeleton, is correlated with the chemical character of N-amide substituents. Phenyl derivatives stabilize transoid orientation of the N-H triazole and C=O amide bonds, whereas the alkyl (methylene or methine) spacer promotes cisoid orientation of these bonds and provides possibility for an intramolecular hydrogen bonding. The solid-state IR spectra and X-ray analysis indicate three patterns of intermolecular association in this series of crystals. Hydrogen bonds observed in crystals influence positions of vibrational bands corresponding to m NH (3322-3180 cm -1 ), m C=O (1634-1676 cm -1 ), and d NH (1600-1500 cm -1 ).

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Section: Ir Spectroscopysupporting

confidence: 92%

Self-assembly of amides of endo-3-(3-methylthio-1H-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid directed by N-amide substituents

et al. 2010

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“…Many important chemical and physical properties of biological and chemical systems can be predicted from the first principles by various computational techniques. 12,13 In recent years, density functional theory (DFT) has been a shooting star in theoretical modeling. The development of better and better exchange-correlation functionals made it possible to calculate many molecular properties with comparable accuracies to traditional correlated ab initio methods, with more favorable computational costs.…”

Section: Introductionmentioning

confidence: 99%

Experimental and Computational Approaches to the Molecular Structure of 3-(2-Mercaptopyridine)phthalonitrile

Tanak¹,

Köysal²,

Işık³

et al. 2011

Bulletin of the Korean Chemical Society

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The compound 3-(2-Mercaptopyridine)phthalonitrile has been synthesized and characterized by IR, UV-vis, and X-ray single-crystal determination. The molecular geometry from X-ray determination of the title compound in the ground state has been compared using the Hartree-Fock (HF) and density functional theory (DFT) with the 6-31G(d) basis set. The calculated results show that the DFT and HF can well reproduce the structure of the title compound. The energetic behavior of the title compound in solvent media was examined using the B3LYP method with the 6-31G(d) basis set by applying the Onsager and polarizable continuum model. Using the TD-DFT and TD-HF methods, electronic absorption spectra of the title compound have been predicted and good agreement with the TD-DFT method and the experimental determination was found. The predicted nonlinear optical properties of the title compound are much greater than those of urea. Besides, molecular electrostatic potential of the title compound were investigated by theoretical calculations. The thermodynamic properties of the compound at different temperatures have been calculated and corresponding relations between the properties and temperature have also been obtained.

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“…Triazole derivatives are used in the synthesis of antibiotics, herbicides, fungicides, plant growth hormone regulators, and potentially good corrosion inhibitors [2,3]. The 1,2,4-triazole system is also of magnetochemical interest because it is able to act as a bridge between metal centres and mediate exchange coupling [4].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1,2,4-trizolophenyl-(2-chloroacetamidebenzenethio)- 4-chlorophenylacetone, C25H20Cl2N4O2S

Ying-Lei¹,

Liu²,

De-Bao³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialTo asolution of 1.2 g(0.004 mol) 1-(4-chloro-phenyl)-3-phenyl-2-(1,2,4-trizolo-1-yl)-2-2propyleno-1-one [1] in 20 ml methanol was added 0.5 g(0.004 mol) of o-aminothiophenol. The mixture was heated under reflux for 30 minutes. Added dropwise of 1.2 ml CF 3 COOH into the mixture when it clears, the refluxing was continued for 3hours. Then the solution was allowed to stand at room temperature for night. The crystalline solid product 2-phenyl-3-(1,2,4-trizolo)-4-(4-chloro-phenyl)-[1,5]benzothiaze-pine was filtered, washed with 2-3 ml of cool methanol and dried, then recrystallized from methanol. 0.2 g(1.5 mmol) chloracetyl chloride was added under stirring to asolution of 0.8 g(1.5 mmol) 2-phenyl-3-(1,2,4-trizolo)-4-(4-chloro-phenyl)-[1,5]benzothiazepine in 30 ml methylene chloride, and asolution of 0.151 g(1.5 mmol) triethylamine in the same solvent (5 ml) was added dropwise slowly. The reaction mixture was continued under stirring for 48 hours at room temperature. After complete reaction (by TLC monitoring), the solvent was evaporated at reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/light petroleum (v/v =1 :8). Then the colorless crystals of title compound were obtained. Experimental detailsThe Hatoms bonded to Cwere positioned geometrically and refined using ariding model. The Hatom bonded to Natom was found by difference Fourier methods and refined with N-Hdistance restrained to 0.84(2) Å. DiscussionTriazole derivatives are used in the synthesis of antibiotics, herbicides, fungicides, plant growth hormone regulators, and potentially good corrosion inhibitors [2,3]. The 1,2,4-triazole system is also of magnetochemical interest because it is able to act as a bridge between metal centres and mediate exchange coupling [4]. The crystal structure of the title compound is built up by the C 25 H 20 Cl 2 N 4 O 2 Sm olecules, in which the bond lengths are in normal ranges. The C19-O2 (1.213(2) Å)and N1-H(0.84(2) Å)bonds are as same as the normal bonds, so hydrogen bonds are not formed, the C19-O2 and N1-Hbonds are not in identical plane. The molecules are interlinked by O···H, N···H, Cl···Cl and Cl···Hwhat generated three-dimensional network.

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Novel compounds of 4-amino-1,2,4-triazole with dicarboxylic acids – crystal structures, vibrational spectra and non-linear optical properties

Cited by 85 publications

References 41 publications

Self-assembly of amides of endo-3-(3-methylthio-1H-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid directed by N-amide substituents

Self-assembly of amides of endo-3-(3-methylthio-1H-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid directed by N-amide substituents

Experimental and Computational Approaches to the Molecular Structure of 3-(2-Mercaptopyridine)phthalonitrile

Crystal structure of 1,2,4-trizolophenyl-(2-chloroacetamidebenzenethio)- 4-chlorophenylacetone, C25H20Cl2N4O2S

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