Pentazole-Based Energetic Ionic Liquids:  A Computational Study

Pimienta, Ian S. O.; Elzey, Sherrie; Boatz, Jerry A.; Gordon, Mark S.

doi:10.1021/jp0663006

Cited by 32 publications

(33 citation statements)

References 49 publications

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“…As shown in previous studies, [80][81][82] ionic liquid ion pairs have a definite separation of charge (approximately +1 on the cations and -1 on the anions) at equilibrium geometries. This charge separation is also observed for tetramers, as shown in Table 2, and the charge separation between cations and anions is still present up to hexamer structures.…”

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

confidence: 72%

“…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%

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

confidence: 72%

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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“…Replacing a hydrogen atom with functional substituents resulted in similar observations as made from previous work on the smaller azole analogs . As a general feature, most EDGs result in lower heats of formation while most EWGs lead to higher values.…”

Section: Resultssupporting

confidence: 89%

“…The calculated heats of formation will be used to quantify the energy content of these compounds. Previous studies have measured the contributions of additional nitrogen atoms to the calculated heats of formation for a few azole cations . The results show an increase of about 31 kcal/mol per nitrogen atom added in the cations triazolium, tetrazolium, and pentazolium.…”

Section: Resultsmentioning

confidence: 87%

Heats of formation and thermal stability of substituted 1,1′‐Azobis(tetrazole) compounds with an extended nitrogen chain

Pimienta

Patkowski

2018

Int J of Quantum Chemistry

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The molecular structures of 1,1′‐Azobis(tetrazole) (N10) and monosubstituted compounds involving F, CH3, CN, NH2, OH, OCH3, N3, NF2, NO2, and CH2NO2 groups are investigated using density functional theory. The heats of formation of these compounds are investigated using ab initio composite methods. Intrinsic reaction coordinate calculations are performed to determine the energies along the decomposition pathways. The optimized geometries of the N10 compounds indicate planar configurations consisting of aromatic nitrogen–nitrogen and carbon–nitrogen bonds. The stability and energy content of the substituted compounds are highly correlated with the nature of the substituents. Electron‐donating groups reduce the heats of formation but increase the exothermicity of the decomposition. The decomposition of the N10 compounds is classified into two general pathways: (1) a scheme involving straight‐up decomposition and (2) a scheme involving functional rearrangement. Compounds undergoing decomposition pathway (1) are more exothermic with lower rate‐determining activation barriers than those undergoing the latter pathway (2).

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“…[35][36][37] Recently a study by Stoimenovski et al 38 showed that combining primary and tertiary amines of similar pK aq a values with a common acid (acetic acid) resulted in ionic liquids of various degree of ionisation. Protic ionic liquids with primary amines exhibited close-to-ideal behaviour on the Walden plot, whereas tertiary amines formed fluid mixtures with a very low degree of ionisation.…”

Section: Types Of Interactions In Ionic Liquids: a Theoretical Perspementioning

confidence: 99%

Towards large-scale, fully ab initio calculations of ionic liquids

Izgorodina

2011

Phys. Chem. Chem. Phys.

121

101

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Ionic liquids have attracted a substantial amount of interest as replacement of traditional electrolytes in high efficiency electrochemical devices for generation and storage of energy due to their superior physical and chemical properties, especially low volatility and high electrochemical stability. For enhanced performance of the electrochemical devices ionic liquids are required to be highly conductive and low viscous. Long-range Coulomb and short-range dispersion interactions between ions affect physical and chemical properties of ionic liquids in a very complex way, thus preventing direct correlations to the chemical structure. Considering a vast combination of available cations and anions that can be used to synthesize ionic liquids, development of predictive theoretical approaches that allow for accurate tailoring of their physical properties has become crucial to further enhance the performance of electrochemical devices such as lithium batteries, fuel and solar cells. This perspective article gives a thorough overview of current theoretical approaches applied for studying thermodynamic (melting point and enthalpy of vapourisation) and transport (conductivity and viscosity) properties of ionic liquids, emphasizing their reliability and limitations. Strategies for improving predictive power and versatility of existing theoretical approaches are also outlined.

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Pentazole-Based Energetic Ionic Liquids: A Computational Study

Cited by 32 publications

References 49 publications

Accurate Methods for Large Molecular Systems

Accurate Methods for Large Molecular Systems

Heats of formation and thermal stability of substituted 1,1′‐Azobis(tetrazole) compounds with an extended nitrogen chain

Towards large-scale, fully ab initio calculations of ionic liquids

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