Comparative semiempirical calculations of tetrazole derivatives

Ивашкевич, Олег А.; Гапоник, П. Н.; Koren, Andrei O.; Bubel, O. N.; Fronchek, E. V.

doi:10.1002/qua.560430608

Cited by 34 publications

(6 citation statements)

References 41 publications

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“…It may be easily observed that the greatest negative charges lie on N 1 and N 4 , as semiempirical methods also indicated for the parent 1H-tetrazole [21], although in the present system, a large negative charge may be found in the exocyclic sulfur as well.…”

Section: Structure Of the Ionic Moietiesmentioning

confidence: 81%

Structural studies of tetrazoles. Crystal and molecular structure and ab initio calculations of 1-phenyl-1H-tetrazole-5-thiolate, as its [diaqua(18-crown-6)sodium] salt: An anionic tetrazole free of direct metal interactions

Jimnez-Sandoval¹,

Cea‐Olivares²,

Hernndez-Ortega³

et al. 1997

Heteroat. Chem.

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Section: Structure Of the Ionic Moietiesmentioning

confidence: 81%

Structural studies of tetrazoles. Crystal and molecular structure and ab initio calculations of 1-phenyl-1H-tetrazole-5-thiolate, as its [diaqua(18-crown-6)sodium] salt: An anionic tetrazole free of direct metal interactions

Jimnez-Sandoval¹,

Cea‐Olivares²,

Hernndez-Ortega³

et al. 1997

Heteroat. Chem.

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“…The unimolecular decomposition of 5-ITZ has not been previously investigated with quantum chemical methods, although Ivashkevich et al determined the structures of 5-ITZ at the semiempirical level of theory and found agreement with the experimental results of Nelson and Baglin . To aid in determining the mechanism of 5-ITZ unimolecular decomposition, 80 SR-IPS runs were performed on isopotential hypersurfaces ranging between 325 and 450 kJ/mol.…”

Section: Resultsmentioning

confidence: 99%

Unimolecular Decomposition of 5-Aminotetrazole and its Tautomer 5-Iminotetrazole: New Insight from Isopotential Searching

2009

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Aminotetrazole compounds have become attractive ingredients in gas generating compositions, solid rocket propellants, and green pyrotechnics. Therefore, a fundamental understanding of their thermal decomposition mechanisms and thermodynamics is of great interest. In this study, the specular reflection isopotential searching method was used to investigate the unimolecular decomposition mechanisms of 5-iminotetrazole (5-ITZ), 1H-5-aminotetrazole (1H-5-ATZ), and 2H-5-aminotetrazole (2H-5-ATZ). Subsequent thermochemical analysis of the unimolecular decomposition pathways was performed at the CCSD(T)/aug-cc-pVTZ//B3LYP/6-311++G(3df,3pd) level of theory. Based upon the relative reaction barriers predicted in this study, the initial gaseous products of 5-ITZ unimolecular decomposition are HN 3 and NH 2 CN (calculated activation barrier equal to 199.5 kJ/mol). On the other hand, the initial gaseous products of 1H-5-ATZ and 2H-5-ATZ unimolecular decomposition are predicted to be N 2 and metastable CH 3 N 3 (calculated activation barriers equal to 169.2 and 153.7 kJ/mol, respectively). These predicted unimolecular decomposition products and activation barriers are in excellent agreement with thermal decomposition experiments performed by Lesnikovich et al.

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“…To our knowledge, no theoretically computed HOFs for tetrazole derivatives with DFT method, other than our recent work, are reported, though experimental HOFs for some tetrazole compounds were presented. − We only found several semiempirical MO calculations − in this subject. Series investigations ,− on tetrazole derivatives show that electron correlation effects in tetrazoles are great.…”

Section: Introductionmentioning

confidence: 80%

Studies on Heats of Formation for Tetrazole Derivatives with Density Functional Theory B3LYP Method

et al. 1999

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The heats of formation (HOF) for 49 tetrazole derivatives are calculated with the density functional theory (DFT) B3LYP method by means of designed isodemic and isogyric reactions. The average absolute deviation for five compounds for which the experimental HOFs are available is less than 2 kcal/mol target accuracy of G-2 theory. It has been demonstrated that for compounds involving delocalized bonds, choosing molecules containing all of the delocalized bonds as reference compounds is an appropriate approach. The calculated HOFs indicate that most neutral 2H-isomers are more stable than the corresponding 1H-isomers whereas the 1-substituted tetrazolate anions are more stable than the corresponding 2-substituted ones. Furthermore, our results consistently show that C-substituted tetrazoles are more stable than the corresponding N-substituted isomers. Our calculated heat of formation calls into question the experimental heat of formation of 2-methyltetrazole.

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Comparative semiempirical calculations of tetrazole derivatives

Cited by 34 publications

References 41 publications

Structural studies of tetrazoles. Crystal and molecular structure and ab initio calculations of 1-phenyl-1H-tetrazole-5-thiolate, as its [diaqua(18-crown-6)sodium] salt: An anionic tetrazole free of direct metal interactions

Structural studies of tetrazoles. Crystal and molecular structure and ab initio calculations of 1-phenyl-1H-tetrazole-5-thiolate, as its [diaqua(18-crown-6)sodium] salt: An anionic tetrazole free of direct metal interactions

Unimolecular Decomposition of 5-Aminotetrazole and its Tautomer 5-Iminotetrazole: New Insight from Isopotential Searching

Studies on Heats of Formation for Tetrazole Derivatives with Density Functional Theory B3LYP Method

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