Triazolium-Based Energetic Ionic Liquids

Schmidt, Michael W.; Gordon, Mark S.; Boatz, Jerry A.

doi:10.1021/jp058149q

Cited by 169 publications

(157 citation statements)

References 78 publications

(111 reference statements)

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“…2 The diagonal density matrix elements give the electron occupancy of the localized molecular orbitals. The off-diagonal elements give the bond orders.…”

Section: Resultsmentioning

confidence: 99%

“…47 MP2/6-31++G(d,p) calculations on 1,2,4-triazolium dinitramide typically do not give stable ion pairs. 2 The most recent MP2 calculations done on three ion pairs of 1,2,4-triazolium dinitramide, show that the six ion cluster is only 1.0 kcal/mol higher in energy than the six neutral cluster. 48 This is caused by an increase in charge balance that occurs as the number of ion pairs present increases.…”

Section: Resultsmentioning

confidence: 99%

“…A thorough study of the 1,2,4-triazolium cation has recently been published. 2 The focus of the present study is on the electronic structure of the tetrazolium cation.…”

Section: Introductionmentioning

confidence: 99%

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Electronic Structure Studies of Tetrazolium-Based Ionic Liquids

2006

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New energetic ionic liquids are investigated as potential high energy density materials. Ionic liquids are composed of large, charge-diffuse cations, coupled with various (usually oxygen containing) anions. In this work, calculations have been performed on the tetrazolium cation with a variety of substituents. Density functional theory (DFT) with the B3LYP functional, using the 6-311G(d,p) basis set was used to optimize geometries. Improved treatment of dynamic electron correlation was obtained using second-order perturbation theory (MP2). Heats of formation of the cation with different substituent groups were calculated using isodesmic reactions and Gaussian-2 calculations on the reactants. The cation was paired with oxygen rich anions ClO4-, NO3-, or N(NO2)2-and those structures were optimized using both DFT and MP2. The reaction pathway for proton transfer from the cation to the anion was investigated. Disciplines Chemistry CommentsReprinted (adapted) ReceiVed: February 9, 2006; In Final Form: April 3, 2006 New energetic ionic liquids are investigated as potential high energy density materials. Ionic liquids are composed of large, charge-diffuse cations, coupled with various (usually oxygen containing) anions. In this work, calculations have been performed on the tetrazolium cation with a variety of substituents. Density functional theory (DFT) with the B3LYP functional, using the 6-311G(d,p) basis set was used to optimize geometries. Improved treatment of dynamic electron correlation was obtained using second-order perturbation theory (MP2). Heats of formation of the cation with different substituent groups were calculated using isodesmic reactions and Gaussian-2 calculations on the reactants. The cation was paired with oxygen rich anions ClO 4 -, NO 3 -, or N(NO 2 ) 2 -and those structures were optimized using both DFT and MP2. The reaction pathway for proton transfer from the cation to the anion was investigated.

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“…2 The diagonal density matrix elements give the electron occupancy of the localized molecular orbitals. The off-diagonal elements give the bond orders.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Electronic Structure Studies of Tetrazolium-Based Ionic Liquids

2006

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“…The FMO Method Applied to Ionic Liquids. Previous studies of ionic liquids [80][81][82] have focused on the decomposition of ion pairs (Figure 8), providing insight into the chemistry of their ignition as high-energy fuels. The focus of this paper, however, will be to accurately describe larger systems beyond single anion-cation pairs.…”

Section: Fmo2 and Fmo3 Calculations On (H 2 O) 32mentioning

confidence: 99%

Accurate Methods for Large Molecular Systems

et al. 2009

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Three exciting new methods that address the accurate prediction of processes and properties of large molecular systems are discussed. The systematic fragmentation method (SFM) and the fragment molecular orbital (FMO) method both decompose a large molecular system (e.g., protein, liquid, zeolite) into small subunits (fragments) in very different ways that are designed to both retain the high accuracy of the chosen quantum mechanical level of theory while greatly reducing the demands on computational time and resources. Each of these methods is inherently scalable and is therefore eminently capable of taking advantage of massively parallel computer hardware while retaining the accuracy of the corresponding electronic structure method from which it is derived. The effective fragment potential (EFP) method is a sophisticated approach for the prediction of nonbonded and intermolecular interactions. Therefore, the EFP method provides a way to further reduce the computational effort while retaining accuracy by treating the far-field interactions in place of the full electronic structure method. The performance of the methods is demonstrated using applications to several systems, including benzene dimer, small organic species, pieces of the α helix, water, and ionic liquids. RightsWorks produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted. ReceiVed: December 31, 2008; ReVised Manuscript ReceiVed: February 7, 2009 Three exciting new methods that address the accurate prediction of processes and properties of large molecular systems are discussed. The systematic fragmentation method (SFM) and the fragment molecular orbital (FMO) method both decompose a large molecular system (e.g., protein, liquid, zeolite) into small subunits (fragments) in very different ways that are designed to both retain the high accuracy of the chosen quantum mechanical level of theory while greatly reducing the demands on computational time and resources. Each of these methods is inherently scalable and is therefore eminently capable of taking advantage of massively parallel computer hardware while retaining the accuracy of the corresponding electronic structure method from which it is derived. The effective fragment potential (EFP) method is a sophisticated approach for the prediction of nonbonded and intermolecular interactions. Therefore, the EFP method provides a way to further reduce the computational effort while retaining accuracy by treating the far-field interactions in place of the full electronic structure method. The performance of the methods is demonstrated using applications to several systems, including benzene dimer, small organic species, pieces of the R helix, water, and ionic liquids. Authors

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“…The energies of the parent ions in the isodesmic reactions were calculated from protonation reactions (Scheme 3; enthalpy of formation of H þ is 1530 kJ mol À1 ). [37,38] The enthalpy of the isodesmic reaction (DH 0 f ) is obtained by combining the MP2/6-311þþG** energy difference for the reaction, the zero-point energies (B3-LYP/6-31þG**), and other thermal factors(B3-LYP/6-31þG**). Thus, the enthalpy of formation of the cations, anions, and the salt being investigated can be extracted readily according to Further, the impact sensitivity of an energetic material is essential, because it is an important index to guarantee safety for storage or use.…”

Section: Detonation Propertiesmentioning

confidence: 99%

Structure, Thermal Behaviour, and Energetic Properties of 4-Amino-1,2,4-triazole Dinitroguanidine Salt

Jin

Jia

et al. 2014

Aust. J. Chem.

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A novel nitrogen-rich energetic compound 4-amino-1,2,4-triazole dinitroguanidine salt (4-ATDNG) was synthesized and fully characterized. Its crystal, thermal behaviour, and detonation properties were investigated by X-ray diffraction, thermogravimetry-derivative thermogravimetry-differential scanning calorimetry (TG-DTG-DSC) coupling system, and the Kamlet-Jacobs equation. In view of the obtained values such as the critical temperature of thermal explosion (T b , 186.368C), entropy of activation (DS 6 ¼ , 60.22 J mol À1 k À1 ), enthalpy of activation (DH 6 ¼ , 143.24 kJ mol À1 ), free energy of activation (DG 6 ¼ , 116.34 kJ mol À1 ), detonation pressure (P, 29.78 GPa), detonation velocity (V, 8.28 km s À1 ), and impact sensitivity (h 50 ¼ 135 cm), it is proposed that 4-ATDNG possesses excellent thermal stability and has the potential to be a useful energetic material in the future.

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Triazolium-Based Energetic Ionic Liquids

Cited by 169 publications

References 78 publications

Electronic Structure Studies of Tetrazolium-Based Ionic Liquids

Electronic Structure Studies of Tetrazolium-Based Ionic Liquids

Accurate Methods for Large Molecular Systems

Structure, Thermal Behaviour, and Energetic Properties of 4-Amino-1,2,4-triazole Dinitroguanidine Salt

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