Multilevel quantum chemical calculation of the enthalpy of formation of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]-tetrazine-4,6-di-N-dioxide

Kiselev, Vitaly G.; Gritsan, Nina P.; Зарко, В. Е.; Kalmykov, P. I.; Shandakov, V. A.

doi:10.1007/s10573-007-0074-6

Cited by 33 publications

(11 citation statements)

References 11 publications

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“…As another example, consider furazano-1,2,3,4-tetrazine-1, 3-dioxide (FTDO, 8), in which there has recently been considerable interest [63][64][65]. Its measured density and heat of formation have been reported to be 1.85 g/cm 3 and 160.9 kcal mol -1 [65].…”

Section: Heat Of Detonation and The Design Of Energetic Compoundsmentioning

confidence: 99%

Impact sensitivity and the maximum heat of detonation

2015

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Section: Heat Of Detonation and The Design Of Energetic Compoundsmentioning

confidence: 99%

Impact sensitivity and the maximum heat of detonation

2015

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“…[21][22][23] The methods of electronic structure calculation used in this study include the ab initio CBS-QB3, G3MP2B3 and G4 composite methods along with the B3LYP/6-31+G(2d,p), M06-2X/6-311+G(2d,p), and B97XD/6-311+G(2d,p) DFT methods. [24][25][26][27][28][29][30][31] The composite CBS-QB3 calculation method has been used for the thermochemical properties, to achieve improvements on the accuracy over the DFT methods. The CBS-QB3 method utilizes the B3LYP/6-311G(2d,d,p) level of theory to obtain the optimized lowest energy geometries and to calculate vibration frequencies, it then uses CCSD(T), MP4(SDQ), and MP2 calculations to determine single-point energies.…”

Section: Calculation Methodsmentioning

confidence: 99%

Reaction kinetics and thermochemistry of the chemically activated and stabilized primary ethyl radical of methyl ethyl sulfide, CH₃SCH₂CH₂•, with O₂ to CH₃SCH₂CH₂OO•

Song

Bozzelli

2019

Int J of Chemical Kinetics

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Oxidation of methyl ethyl sulfide (CH 3 SCH 2 CH 3 , methylthioethane, MES) under atmospheric and combustion conditions is initiated by hydroxyl radicals, MES radicals, generated after loss of a H atom via OH abstraction, will further react with O 2 to form chemically activated and stabilized peroxyl radical adducts. The kinetics of the chemically activated reaction between the CH 3 SCH 2 CH 2 • radical and molecular oxygen are analyzed using quantum Rice-Ramsperger-Kassel theory for k(E) with master equation analysis and a modified strong-collision approach to account for further reactions and collisional deactivation. Thermodynamic properties of reactants, products, and transition states are determined by the B3LYP/6-31+G(2d,p), M062X/6-311+G(2d,p), B97XD/6-311+G(2d,p) density functional theory, and CBS-QB3, G3MP2B3, and G4 composite methods. The reaction of CH 3 SCH 2 CH 2 • with O 2 forms an energized peroxy adduct CH 3 SCH 2 CH 2 OO• with a calculated well depth of 34.1 kcal mol −1 at the CBS-QB3 level of theory. Thermochemical properties of reactants, transition states, and products obtained under CBS-QB3 level are used for calculation of kinetic parameters. Reaction enthalpies are compared between the methods. The temperature and pressure-dependent rate coefficients for both the chemically activated reactions of the energized adduct and the thermally activated reactions of the stabilized adducts are presented. Stabilization and isomerization of the CH 3 SCH 2 CH 2 OO• adduct are important under high pressure and low temperature.At higher temperatures and atmospheric pressure, the chemically activated peroxy adduct reacts to new products before stabilization. Addition of the peroxyl oxygen radical to the sulfur atom followed by sulfur-oxygen double bond formation and elimination of the methyl radical to form S(= O)CCO• + CH 3 (branching) is a potentially important new pathway for other alkyl-sulfide peroxy radical systems under thermal or combustion conditions. K E Y W O R D Skinetics, methyl ethyl sulfide, oxidation, thermochemistry 618

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“…Molecular structures and vibrational frequencies were determined at the B3LYP/6‐311G (2d,d,p) in the CBS‐QB3 level of calculation, which is considered accurate for the calculation of electronic structure and energies of the first and second row atoms . The Complete Basis Set‐QB3 multi‐level method was developed by the research group of G. Peterson and Kiselev et al The CBS‐QB3 multilevel method is based on the optimized geometries at the B3LYP/6‐311G(2d,d,p) level.…”

Section: Methodsmentioning

confidence: 99%

Structures and thermochemistry of methyl ethyl sulfide and its hydroperoxides: HOOCH₂SCH₂CH₃, CH₃SCH(OOH)CH₃, CH₃SCH₂CH₂OOH, and radicals

Song

Bozzelli

2017

J of Physical Organic Chem

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Hydroperoxides and the corresponding peroxy radicals are important intermediates during the partial oxidation of methyl ethyl sulfide (CH3SCH2CH3) in both atmospheric chemistry and in combustion. Structural parameters, internal rotor potentials, bond dissociation energies, and thermochemical properties (ΔHfo, So and Cp(T)) of 3 corresponding hydroperoxides CH2(OOH)SCH2CH3, CH3SCH(OOH)CH3, CH3SCH2CH2OOH of methyl ethyl sulfides, and the radicals formed via loss of a hydrogen atom are important to understanding the oxidation reactions of MES. The lowest energy molecular structures were identified using the density functional B3LYP/6‐311G(2d,d,p) level of theory. Standard enthalpies of formation (ΔHfo298) for the radicals and their parent molecules were calculated using the density functional B3LYP/6‐31G(d,p), B3LYP/6‐31 + G(2d,p), and the composite CBS‐QB3 ab initio methods. Isodesmic reactions were used to determine ∆Hfo values. Internal rotation potential energy diagrams and rotation barriers were investigated using the B3LYP/6‐31G(d,p) level theory. Contributions for So298 and Cp(T) were calculated using the rigid rotor harmonic oscillator approximation based on the structures and vibrational frequencies obtained by the density functional calculations, with contributions from torsion frequencies replaced by internal rotor contributions. The recommended values for enthalpies of formation of the most stable conformers of CH3SCH2CH2, CH2(OOH)SCH2CH3, CH3SCH(OOH)CH3, and CH3SCH2CH2OOH are −14.0, −33.0, −37.2, and −32.7 kcal/mol, respectively. Group additivity values were developed for estimating properties of structurally similar and larger sulfur‐containing peroxides. Groups for use in group additivity estimation of sulfur peroxide thermochemical properties were developed.

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Multilevel quantum chemical calculation of the enthalpy of formation of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]-tetrazine-4,6-di-N-dioxide

Cited by 33 publications

References 11 publications

Impact sensitivity and the maximum heat of detonation

Impact sensitivity and the maximum heat of detonation

Reaction kinetics and thermochemistry of the chemically activated and stabilized primary ethyl radical of methyl ethyl sulfide, CH₃SCH₂CH₂•, with O₂ to CH₃SCH₂CH₂OO•

Structures and thermochemistry of methyl ethyl sulfide and its hydroperoxides: HOOCH₂SCH₂CH₃, CH₃SCH(OOH)CH₃, CH₃SCH₂CH₂OOH, and radicals

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Multilevel quantum chemical calculation of the enthalpy of formation of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]-tetrazine-4,6-di-N-dioxide

Cited by 33 publications

References 11 publications

Impact sensitivity and the maximum heat of detonation

Impact sensitivity and the maximum heat of detonation

Reaction kinetics and thermochemistry of the chemically activated and stabilized primary ethyl radical of methyl ethyl sulfide, CH3SCH2CH2•, with O2 to CH3SCH2CH2OO•

Structures and thermochemistry of methyl ethyl sulfide and its hydroperoxides: HOOCH2SCH2CH3, CH3SCH(OOH)CH3, CH3SCH2CH2OOH, and radicals

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Reaction kinetics and thermochemistry of the chemically activated and stabilized primary ethyl radical of methyl ethyl sulfide, CH₃SCH₂CH₂•, with O₂ to CH₃SCH₂CH₂OO•

Structures and thermochemistry of methyl ethyl sulfide and its hydroperoxides: HOOCH₂SCH₂CH₃, CH₃SCH(OOH)CH₃, CH₃SCH₂CH₂OOH, and radicals