Spectroscopy of jet-cooled benzimidazole and benzotriazole

Jalviste, Erko; Treshchalov, Alexey

doi:10.1016/0301-0104(93)80127-u

Cited by 36 publications

(33 citation statements)

References 20 publications

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“…7 All the peculiarities of the fluorescence excitation spectrum of BtH at 70°С are explained by the presence of the 2Н-tautomer. 1,6 The complete optimization of the geometry at the MP2-6-31G** level leads to a ∆E 1H→2H (-2.5 kcal mol -1 ) closer to the experimental results (≈ -4 kcal mol -1 ). 1 The 1H-tautomer was found to be predominant in the solid state and solution.…”

Section: Introductionsupporting

confidence: 51%

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The synthesis and stereoelectronic structure of 1- and 2-(trimethoxysilylmethyl)- and 1- and 2-(silatranylmethyl)benzotriazole

Воронков¹,

Trofimova²,

Brodskaya³

et al. 2003

Arkivoc

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Only 2-benzotriazolyl sodium is formed in the reaction of benzotriazole (BtH) with sodium methoxide. Its reaction with trimethyl-or trimethoxy-(chloromethyl)-silane affords a mixture of 1-and 2-(trimethylsilylmethyl)-1 and 2, and 1-and 2-(trimethoxysilylmethyl)benzotriazoles, 3 and 4, which were separated into the individual isomers. trans-Etherification of the latter with tris-(2-hydroxyethyl)amine leads to 1-and 2-(silatranylmethyl)benzotriazoles 5 and 6. The electronic structures of the compounds prepared were investigated using IR, UV, multinuclear NMR spectroscopy, mass spectrometry, and X-ray diffraction. The organosilicon benzotriazole derivatives 1, 3 and 5 show a benzenoid structure, whereas 2, 4 and 6 have ortho-quinonoid structures.

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Section: Introductionsupporting

confidence: 51%

“…[2][3][4] IR Spectra show that BtH in the gas phase at 140°С is mainly represented by the 1Н-tautomer. [5][6][7][8] The microwave spectrum at 90°С has established only 1H-BtH. 7 All the peculiarities of the fluorescence excitation spectrum of BtH at 70°С are explained by the presence of the 2Н-tautomer.…”

Section: Introductionmentioning

confidence: 99%

The synthesis and stereoelectronic structure of 1- and 2-(trimethoxysilylmethyl)- and 1- and 2-(silatranylmethyl)benzotriazole

Воронков¹,

Trofimova²,

Brodskaya³

et al. 2003

Arkivoc

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show abstract

“…They show pharmaceutical activity, 1 -7 such as lowering of blood sugar level, inhibition of phosphodiesterase-5, 8 as well as casein kinase-2 and -5. 9 They exhibit also fungicidal, 10 anti-hypertensive, 11 anti-diabetic 12 and sedative 13 activities. Spectroscopic properties of BI 14 -16 and its derivatives 17 -19 have been studied previously.…”

Section: Introductionmentioning

confidence: 99%

Vibrational spectra, X‐ray and molecular structure of 1H‐ and 3H‐imidazo[4,5‐b]pyridine and their methyl derivatives: DFT quantum chemical calculations

Lorenc

Dymińska

Talik

et al. 2007

J Raman Spectroscopy

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Molecular structure, vibrational energy levels and potential energy distribution of 1H-imidazo[4,5-b]pyridine, 3H-imidazo[4,5-b]pyridine, 5-methyl-1H-imidazo[4,5-b]pyridine, 6-methyl-1H-imidazo[4,5-b]pyridine and 7-methyl-3H-imidazo[4,5-b]pyridine were determined using density functional theory (DFT) at the B3LYP/6-31G(d,p) level. The optimised bond lengths and bond angles are in good agreement with the X-ray data of 5-methyl-1H-imidazo[4,5-b]pyridine obtained in the present work (Pbca space group; a = 8.660.2/, b = 11.078.2/, c = 11.078.3/Å, Z = 8). The N + H group plays the role of a proton donor in a medium strong hydrogen bond of the type N-H· · ·N, linking the N-atom of the pyridine with the adjacent molecule related by the symmetry operation: 1/2 − x, y − 1/2, z(N· · ·N = 2.869.25/Å). The presence of hydrogen bond is confirmed by appearance in the IR spectra of a very broad and strong contour in the 2000-3100 cm −1 range. The place of substitution of the methyl group at the pyridine ring influences the proton position of the NH group at the imidazole unit.

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“…The problem of the relative stability of the triazoletautomers has been the subject of several theoretical [27,[61][62][63] and experimental [21,22,26,[63][64][65][66] studies, where 1H-and 2H-benzotriazoles were taken as an example. Ab initio calculations proved a higher stability of the 1H-tautomer in agreement with the statement that this tautomer prevails in the solid phase [52] and gas phase [21].…”

Section: Discussion Of the Vibrational Spectra Of The Methyl Tp Derivmentioning

confidence: 99%

Vibrational dynamics and molecular structure of 1H- and 3H-1,2,3-triazolo[4,5-b]pyridine and its methyl-derivatives based on DFT chemical quantum calculations

et al. 2007

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Spectroscopy of jet-cooled benzimidazole and benzotriazole

Cited by 36 publications

References 20 publications

The synthesis and stereoelectronic structure of 1- and 2-(trimethoxysilylmethyl)- and 1- and 2-(silatranylmethyl)benzotriazole

The synthesis and stereoelectronic structure of 1- and 2-(trimethoxysilylmethyl)- and 1- and 2-(silatranylmethyl)benzotriazole

Vibrational spectra, X‐ray and molecular structure of 1H‐ and 3H‐imidazo[4,5‐b]pyridine and their methyl derivatives: DFT quantum chemical calculations

Vibrational dynamics and molecular structure of 1H- and 3H-1,2,3-triazolo[4,5-b]pyridine and its methyl-derivatives based on DFT chemical quantum calculations

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