Conformations and rotational barriers of 2,2′-bi-1H-imidazole Semiempirical, ab initio, and density functional theory calculations

We performed theoretical studies to predict the molecular structure, molecular properties, and explosive performance of 4,4′,5,5′‐tetranitro‐2,2′‐bi‐1H‐imidazole (TNBI). High levels of ab initio and density functional theories were employed to predict the molecular structure of TNBI. Predicted TNBI structure was in good agreement with that observed by X‐ray crystallography. Heat of formation in the solid phase at 298 K was predicted to be 270.3 kJ/mol. Density of TNBI was predicted to be 1.919–1.956 g/cm3 depending upon the parameter sets of group additivity method. By using these values as input data, we estimated detonation velocity and C–J pressure to be 8.69–8.80 km/s and 34.5‐36.1 GPa, respectively. Impact sensitivity of TNBI was predicted to be 33 cm.

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Theoretical Studies on Molecular and Explosive Properties of 4,4′,5,5′‐Tetranitro‐2,2′‐bi‐1H‐imidazole (TNBI)

Cho

Goh

Cho

et al. 2006

Propellants Explo Pyrotec

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X-Ray structures and ab initio study of the conformational properties of novel oxazole and thiazole containing di- and tripeptide mimetics †

Kaiser

Videnov

Maichle‐Mößmer

et al. 2000

J. Chem. Soc., Perkin Trans. 2

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X-Ray crystal structures of Boc-protected derivatives of the novel di-and tripeptide mimetics 2-aminomethyl-1,3oxazole-4-carboxylic acid, 2-aminomethyl-1,3-thiazole-4-carboxylic acid, 2-(2Ј-aminomethyl-1Ј,3Ј-oxazol-4Ј-yl)-1,3thiazole-4-carboxylic acid (gly(OxaThz)), and 2-(2Ј-aminomethyl-1,3-thiazol-4Ј-yl)-1,3-thiazole-4-carboxylic acid (gly(ThzThz)) have been determined. Furthermore conformational properties of the bicyclic compounds have been investigated by ab initio calculations at the HF and DFT level. According to the calculations for the bicyclic compounds the anti conformation is energetically more stable by about 20 kJ mol Ϫ1 (HF/6-31G(d)) for gly(ThzThz) and gly(OxaThz) while in the case of gly(ThzOxa) the difference is only about 4 kJ mol Ϫ1 . The rotational barrier is about 28 kJ mol Ϫ1 for the anti→syn conversion. Calculations at the DFT level with a 3-21G(d) basis set yielded similar results.

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Conformations and rotational barriers of 2,2′-bi-1H-imidazole Semiempirical, ab initio, and density functional theory calculations

Cited by 2 publications

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Theoretical Studies on Molecular and Explosive Properties of 4,4′,5,5′‐Tetranitro‐2,2′‐bi‐1H‐imidazole (TNBI)

Theoretical Studies on Molecular and Explosive Properties of 4,4′,5,5′‐Tetranitro‐2,2′‐bi‐1H‐imidazole (TNBI)

X-Ray structures and ab initio study of the conformational properties of novel oxazole and thiazole containing di- and tripeptide mimetics †

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