CRYSTALLOGRAPHIC DATA. 42. Tetrazole

McCrone, Walter C.; Grabar, Donald G.; Lieber, Eugene

doi:10.1021/ac60051a052

Cited by 13 publications

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“…In order to establish that this triclinic form of tetrazole was indeed identical with that reported by McCrone et al (1957), we simulated a powder diffraction pattern using the single-crystal intensity data and the associated lattice parameters (Bartsch & Goddard, 1996). There was a good agreement between the d values and I/ll intensities for all the principal lines.…”

Section: Commentmentioning

confidence: 83%

“…McCrone, Grabar & Lieber (1957) reported the crystallographic data of tetrazole crystals derived from crystal morphology measurements and X-ray diffraction data. They concluded that tetrazole crystallizes in a triclinic unit cell of dimensions a = 5.00, b = 5.46, c = 3.75 ,~, a = 130, /3 = 111 and 7 = 63 °, but the crystal structure was not determined.…”

Section: Commentmentioning

confidence: 99%

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α-1H-1,2,3,4-Tetrazole

Goddard¹,

Heinemann²,

Krüger³

1997

Acta Crystallogr C

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Section: Commentmentioning

confidence: 83%

Section: Commentmentioning

confidence: 99%

α-1H-1,2,3,4-Tetrazole

Goddard¹,

Heinemann²,

Krüger³

1997

Acta Crystallogr C

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] From a fundamental point of view, tetrazoles are also particularly interesting systems, especially because of the tautomerism they may exhibit and their diversified photochemistry. 1,[21][22][23][24][25][26][27][28][29] Unsubstituted tetrazole, for example, was found to exist exclusively in the crystalline phases as the 1H-tautomer, [30][31][32] whereas in solution and gas phase 1H-and 2H-tautomers coexist, the population of the most polar 1H form increasing with the polarity of the solvent. 21,[33][34][35][36][37] According to the experimental findings, 2H-tetrazole was found to be the lowest energy tautomer in media with a dielectric constant smaller than about 7, while in media with a larger dielectric constant, a reversal of energy takes place and 1H-tetrazole becomes the tautomeric ground state.…”

Section: Introductionmentioning

confidence: 99%

Tautomer Selective Photochemistry in 1-(Tetrazol-5-yl)ethanol

et al. 2010

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A combined matrix isolation FTIR and theoretical DFT/B3LYP/6-311++G(d,p) study of the molecular structure and photochemistry of 1-(tetrazol-5-yl)ethanol [1-TE] was performed. The potential energy surface landscapes of the 1H and 2H tautomers of the compound were investigated and the theoretical results were used to help characterize the conformational mixture existing in equilibrium in the gas phase prior to deposition of the matrices, as well as the conformers trapped in the latter. In the gas phase, at room temperature, the compound exists as a mixture of 12 conformers (five of the 1H tautomer and seven of the 2H tautomer). Upon deposition of the compound in an argon matrix at 10 K, only three main forms survive, because the low barriers for conformational isomerization allow extensive conformational cooling during deposition. Deposition of the matrix at 30 K led to further simplification of the conformational mixture with only one conformer of each tautomer of 1-TE surviving. These conformers correspond to the most stable forms of each tautomer, which bear different types of intramolecular H-bonds: 1H-I has an NH · · · O hydrogen bond, whereas 2H-I has an OH · · · N hydrogen bond. Upon irradiating with UV light (λ > 200 nm), a matrix containing both 1H-I and 2H-I forms, an unprecedented tautomer selective photochemistry was observed, with the 2H tautomeric form undergoing unimolecular decomposition to azide + hydroxypropanenitrile and the 1H-tautomer being photostable.

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“…From a more fundamental point of view, tetrazolones are also very interesting molecules, because they may exhibit different tautomers [16][17][18][19][20][21][22][23] and might be expected to have a very rich photochemistry [24][25][26][27]. Tautomerism has been found to be important in the tetrazole family in general.…”

Section: Introductionmentioning

confidence: 99%

Photochemistry of 1-phenyl-tetrazolone isolated in solid argon

Gómez‐Zavaglia

Reva

Frija

et al. 2006

Journal of Photochemistry and Photobiology A: Chemistry

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The molecular structure, vibrational spectra, tautomerism and photochemistry of the derivative of tetrazole, 1-phenyl-tetrazolone (C 7 H 6 N 4 O; PT) have been studied by FT-IR matrix isolation spectroscopy and DFT/B3LYP/6-311++G(d,p) calculations. Among the five structures in which PT could be expected to exist (two keto tautomers, one mesoionic olate-form and two different conformers of the hydroxyl tautomer), only the most stable species, 1-phenyl-1,4-dihydro-5H-tetrazol-5-one, could be experimentally observed in low temperature argon matrices. Monomers of this tautomer give rise to an IR spectrum that fits nicely the calculated spectrum obtained at the DFT/B3LYP/6-311++G(d,p) level of theory. In situ UV irradiation (λ > 235 nm) of the matrix-isolated PT induces three main photochemical processes, all of them involving cleavage of the tetrazole ring: e.g. (1) molecular nitrogen loss, with production of 1-phenyl-diaziridin-3-one; this compound reacts subsequently to form 1-aza-1,2,4,6cycloheptatetraene and isocyanic acid (eventually, also to form CO plus phenyldiazene); (2) cleavage of the C (5) -N (1) and N (3) -N (4) tetrazole-ring bonds, with production of phenylazide and isocyanic acid, with phenylazide then losing N 2 to yield as final product 1-aza-1,2,4,6-cycloheptatetraene; and (3) cleavage of the N (1) -N (2) and N (4) -C (5) tetrazole-ring bonds, to yield phenylisocyanate and azide. The observed photochemical processes are distinct from the preferred thermal fragmentation channel, where CO is produced together with a weak IR absorbant species.

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CRYSTALLOGRAPHIC DATA. 42. Tetrazole

Cited by 13 publications

References 0 publications

α-1H-1,2,3,4-Tetrazole

α-1H-1,2,3,4-Tetrazole

Tautomer Selective Photochemistry in 1-(Tetrazol-5-yl)ethanol

Photochemistry of 1-phenyl-tetrazolone isolated in solid argon

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