Ab initio and density functional study of the geometrical, electronic and vibrational properties of 3,4′-bi-1,2,4-triazole

Guédira, F.; Castellà-Ventura, Martine; Zaydoun, S.; Elhajji, A.; Lautié, A.; Idrissi, M. Saidi

doi:10.1016/j.saa.2009.03.024

Cited by 9 publications

(4 citation statements)

References 23 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 authors have studied these compounds and their properties, such as crystal structure [1][2][3][4][5], quantum-chemical calculations on the tautomerism and protonation sites [6][7][8][9][10][11], spectroscopic properties [12][13][14][15][16][17][18][19][20] and thermal decomposition products [21,22]. Guanazole (3,5-diamino-1,2,4-triazole denoted (NH 2 ) 2 TA (Fig.…”

Section: Introductionmentioning

confidence: 99%

Molecular geometry and vibrational studies of 3,5-diamino-1,2,4-triazole using quantum chemical calculations and FT-IR and FT-Raman spectroscopies

Guennoun¹,

jastimi²,

Guédira³

et al. 2011

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…[47]. 1.3048Å (B3LYP) is just 0.0042Å greater than the reported experimental value of 1.309Å for 4-amino-1,2,4-triazol-1-ium hydrogen oxalate (4-atox) and 4-amino-1,2,4-triazole with succinic acid (4-atsuc) [22,34]. The optimized C 2 -N 3 bond length by B3LYP method is 1.3857Å.…”

Section: Molecular Geometrymentioning

confidence: 89%

Vibrational spectroscopic study and NBO analysis on bis(4-amino-5-mercapto-1,2,4-triazol-3-yl) methane using DFT method

Subashchandrabose

Krishnan

Saleem

et al. 2010

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Ab initio and density functional study of the geometrical, electronic and vibrational properties of 3,4′-bi-1,2,4-triazole

Cited by 9 publications

References 23 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

Molecular geometry and vibrational studies of 3,5-diamino-1,2,4-triazole using quantum chemical calculations and FT-IR and FT-Raman spectroscopies

Vibrational spectroscopic study and NBO analysis on bis(4-amino-5-mercapto-1,2,4-triazol-3-yl) methane using DFT method

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