Modeling Photolytic Decomposition of Energetically Functionalized Dodecanes

Nelson, Tammie Renee; Huestis, Patricia Leigh; Manner, Virginia Warren

doi:10.1021/acs.jpca.2c03404

Modeling Photolytic Decomposition of Energetically Functionalized Dodecanes

Journal Article · Tue Oct 04 00:00:00 EDT 2022 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.2c03404· OSTI ID:1893685

^[1]; ^[1]; ^[1]

Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

The photolytic stability of explosives and energetic functional groups is of importance for those who regularly handle or are exposed to explosives in typical environmental conditions. This study models the photolytic degradation of dodecane substituted with various energetic functional groups: azide, nitro, nitrate ester, and nitramine. For the studied molecules, it was found that excitons localize on the energetic functional group, no matter where they were initially formed, and thus, the predominant degradation pathway involves the degradation of the energetic functional group. The relative trends for both 4 and 8 eV excitation energies followed with what is expected from the relative stability of the energetic functional groups to thermal and sub-shock degradation. The one notable exception was the azide functional group; more work should be done to further understand the photolytic effects on the azide functional group.

View Accepted Manuscript (DOE)

Research Organization:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: 89233218CNA000001

OSTI ID:: 1893685

Alternate ID(s):: OSTI ID: 1876768

Report Number(s):: LA-UR-22-24079

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Issue: 40 Vol. 126; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (45)

Predicting Trigger Bonds in Explosive Materials through Wiberg Bond Index Analysis Harper, Lenora K.; Shoaf, Ashley L.; Bayse, Craig A. ChemPhysChem, Vol. 16, Issue 18 https://doi.org/10.1002/cphc.201500773	journal	November 2015
Relationship between the Bond Dissociation Energies and Impact Sensitivities of Some Nitro-Explosives Song, Xiao-Shu; Cheng, Xin-Lu; Yang, Xiang-Dong Propellants, Explosives, Pyrotechnics, Vol. 31, Issue 4 https://doi.org/10.1002/prep.200600042	journal	August 2006
Correlation of Structure and Sensitivity in Inorganic Azides I Effect of Non-Bonded Nitrogen Nitrogen Distances Cartwright, Michael; Wilkinson, Joshua Propellants, Explosives, Pyrotechnics, Vol. 35, Issue 4 https://doi.org/10.1002/prep.200900034	journal	June 2010
Sensitivity and Performance of Energetic Materials Zeman, Svatopluk; Jungová, Marcela Propellants, Explosives, Pyrotechnics, Vol. 41, Issue 3 https://doi.org/10.1002/prep.201500351	journal	April 2016
Computational determination of effects of electric fields upon “trigger linkages” of prototypical energetic molecules Politzer, Peter; Murray, Jane S.; Lane, Pat International Journal of Quantum Chemistry, Vol. 109, Issue 3 https://doi.org/10.1002/qua.21800	journal	January 2009
Collective electronic oscillators for nonlinear optical response of conjugated molecules Tretiak, Sergei; Chernyak, Vladimir; Mukamel, Shaul Chemical Physics Letters, Vol. 259, Issue 1-2 https://doi.org/10.1016/0009-2614(96)00790-7	journal	August 1996
Pulse radiolysis studies on liquid alkanes and related polymers Tagawa, S.; Hayashi, N.; Yoshida, Y. International Journal of Radiation Applications and Instrumentation. Part C. Radiation Physics and Chemistry, Vol. 34, Issue 4 https://doi.org/10.1016/1359-0197(89)90053-2	journal	January 1989
Ranking explosive sensitivity with chemical kinetics derived from molecular dynamics simulations Cawkwell, M. J.; Ferreira, S. R.; Lease, N. Theoretical and Computational Chemistry https://doi.org/10.1016/B978-0-12-822971-2.00007-3	book	March 2022
Artifacts due to trivial unavoided crossings in the modeling of photoinduced energy transfer dynamics in extended conjugated molecules Nelson, Tammie; Fernandez-Alberti, Sebastian; Roitberg, Adrian E. Chemical Physics Letters, Vol. 590 https://doi.org/10.1016/j.cplett.2013.10.052	journal	December 2013
Constant temperature simulations using the Langevin equation with velocity Verlet integration Paterlini, M. Germana; Ferguson, David M. Chemical Physics, Vol. 236, Issue 1-3 https://doi.org/10.1016/s0301-0104(98)00214-6	journal	September 1998
Recent Advances and Perspectives on Nonadiabatic Mixed Quantum–Classical Dynamics Crespo-Otero, Rachel; Barbatti, Mario Chemical Reviews, Vol. 118, Issue 15 https://doi.org/10.1021/acs.chemrev.7b00577	journal	April 2018
Non-adiabatic Excited-State Molecular Dynamics: Theory and Applications for Modeling Photophysics in Extended Molecular Materials Nelson, Tammie R.; White, Alexander J.; Bjorgaard, Josiah A. Chemical Reviews, Vol. 120, Issue 4 https://doi.org/10.1021/acs.chemrev.9b00447	journal	February 2020
NEXMD Software Package for Nonadiabatic Excited State Molecular Dynamics Simulations Malone, Walter; Nebgen, Benjamin; White, Alexander Journal of Chemical Theory and Computation, Vol. 16, Issue 9 https://doi.org/10.1021/acs.jctc.0c00248	journal	July 2020
Nonadiabatic Excited-State Molecular Dynamics for Open-Shell Systems Zhang, Yu; Li, Linqiu; Tretiak, Sergei Journal of Chemical Theory and Computation, Vol. 16, Issue 4 https://doi.org/10.1021/acs.jctc.9b00928	journal	March 2020
Nature of the Trigger Linkage in Explosive Materials Is a Charge-Shift Bond Joy, Jyothish; Danovich, David; Shaik, Sason The Journal of Organic Chemistry, Vol. 86, Issue 21 https://doi.org/10.1021/acs.joc.1c02066	journal	October 2021
Synthesis of Erythritol Tetranitrate Derivatives: Functional Group Tuning of Explosive Sensitivity Lease, Nicholas; Kay, Lisa M.; Brown, Geoffrey W. The Journal of Organic Chemistry, Vol. 85, Issue 7 https://doi.org/10.1021/acs.joc.9b03344	journal	February 2020
Photoactive High Explosives: Linear and Nonlinear Photochemistry of Petrin Tetrazine Chloride Greenfield, Margo T.; McGrane, Shawn D.; Bolme, Cindy A. The Journal of Physical Chemistry A, Vol. 119, Issue 20 https://doi.org/10.1021/acs.jpca.5b02092	journal	May 2015
Ultrafast Photodissociation Dynamics of Nitromethane Nelson, Tammie; Bjorgaard, Josiah; Greenfield, Margo The Journal of Physical Chemistry A, Vol. 120, Issue 4 https://doi.org/10.1021/acs.jpca.5b09776	journal	January 2016
Ranking the Drop-Weight Impact Sensitivity of Common Explosives Using Arrhenius Chemical Rates Computed from Quantum Molecular Dynamics Simulations Cawkwell, M. J.; Manner, V. W. The Journal of Physical Chemistry A, Vol. 124, Issue 1 https://doi.org/10.1021/acs.jpca.9b10808	journal	December 2019
Understanding Explosive Sensitivity with Effective Trigger Linkage Kinetics Cawkwell, Marc J.; Davis, Jack; Lease, Nicholas ACS Physical Chemistry Au, Vol. 2, Issue 5 https://doi.org/10.1021/acsphyschemau.2c00022	journal	June 2022
Density Matrix Analysis and Simulation of Electronic Excitations in Conjugated and Aggregated Molecules Tretiak, Sergei; Mukamel, Shaul Chemical Reviews, Vol. 102, Issue 9 https://doi.org/10.1021/cr0101252	journal	September 2002
Properties of lead azide prepared in molten salt media Egghart, Heinrich C. Inorganic Chemistry, Vol. 6, Issue 11 https://doi.org/10.1021/ic50057a048	journal	November 1967
Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model Dewar, Michael J. S.; Zoebisch, Eve G.; Healy, Eamonn F. Journal of the American Chemical Society, Vol. 107, Issue 13 https://doi.org/10.1021/ja00299a024	journal	June 1985
Two-Dimensional Real-Space Analysis of Optical Excitations in Acceptor-Substituted Carotenoids Tretiak, Sergei; Chernyak, Vladimir; Mukamel, Shaul Journal of the American Chemical Society, Vol. 119, Issue 47 https://doi.org/10.1021/ja9720164	journal	November 1997
Nonadiabatic Excited-State Molecular Dynamics Modeling of Photoinduced Dynamics in Conjugated Molecules Nelson, Tammie; Fernandez-Alberti, Sebastian; Chernyak, Vladimir The Journal of Physical Chemistry B, Vol. 115, Issue 18 https://doi.org/10.1021/jp109522g	journal	May 2011
Screening for energetic compounds based on 1,3-dinitrohexahydropyrimidine skeleton and 5-various explosopheres: molecular design and computational study Duan, Binghui; Liu, Ning; Lu, Xianming Scientific Reports, Vol. 10, Issue 1 https://doi.org/10.1038/s41598-020-75281-5	journal	October 2020
Examining the chemical and structural properties that influence the sensitivity of energetic nitrate esters Manner, Virginia W.; Cawkwell, Marc J.; Kober, Edward M. Chemical Science, Vol. 9, Issue 15 https://doi.org/10.1039/c8sc00903a	journal	January 2018
The effect of nitro groups on N₂ extrusion from aromatic azide-based energetic materials Shoaf, Ashley L.; Bayse, Craig A. New Journal of Chemistry, Vol. 43, Issue 38 https://doi.org/10.1039/c9nj03220g	journal	January 2019
Adiabatic time-dependent density functional methods for excited state properties Furche, Filipp; Ahlrichs, Reinhart The Journal of Chemical Physics, Vol. 117, Issue 16 https://doi.org/10.1063/1.1508368	journal	October 2002
Excitation Energy Transfer in Alkanes. I. Exciton Model Partridge, Roger H. The Journal of Chemical Physics, Vol. 52, Issue 5 https://doi.org/10.1063/1.1673332	journal	March 1970
Excitation Energy Transfer in Alkanes. II. Experimental Demonstration Partridge, Roger H. The Journal of Chemical Physics, Vol. 52, Issue 5 https://doi.org/10.1063/1.1673333	journal	March 1970
Vacuum Ultraviolet Photolysis of Ethane: Molecular Detachment of Hydrogen Okabe, H.; McNesby, J. R. The Journal of Chemical Physics, Vol. 34, Issue 2 https://doi.org/10.1063/1.1701006	journal	February 1961
Vacuum Ultraviolet Photochemistry. IV. Photolysis of Propane Okabe, H.; McNesby, J. R. The Journal of Chemical Physics, Vol. 37, Issue 6 https://doi.org/10.1063/1.1733283	journal	September 1962
Representation independent algorithms for molecular response calculations in time-dependent self-consistent field theories Tretiak, Sergei; Isborn, Christine M.; Niklasson, Anders M. N. The Journal of Chemical Physics, Vol. 130, Issue 5 https://doi.org/10.1063/1.3068658	journal	February 2009
Statistical mechanical theory for non-equilibrium systems. IX. Stochastic molecular dynamics Attard, Phil The Journal of Chemical Physics, Vol. 130, Issue 19 https://doi.org/10.1063/1.3138762	journal	May 2009
First-order nonadiabatic couplings from time-dependent hybrid density functional response theory: Consistent formalism, implementation, and performance Send, Robert; Furche, Filipp The Journal of Chemical Physics, Vol. 132, Issue 4 https://doi.org/10.1063/1.3292571	journal	January 2010
Nonadiabatic coupling vectors for excited states within time-dependent density functional theory in the Tamm–Dancoff approximation and beyond Tavernelli, Ivano; Curchod, Basile F. E.; Laktionov, Andrey The Journal of Chemical Physics, Vol. 133, Issue 19 https://doi.org/10.1063/1.3503765	journal	November 2010
The fluorescence and photofragmentation of liquid saturated hydrocarbons at energies above the photoionization threshold Schwarz, Frederick P.; Smith, Diane; Lias, Sharon G. The Journal of Chemical Physics, Vol. 75, Issue 8 https://doi.org/10.1063/1.442525	journal	October 1981
Molecular dynamics with electronic transitions Tully, John C. The Journal of Chemical Physics, Vol. 93, Issue 2 https://doi.org/10.1063/1.459170	journal	July 1990
Recursive density‐matrix‐spectral‐moment algorithm for molecular nonlinear polarizabilities Tretiak, Sergei; Chernyak, Vladimir; Mukamel, Shaul The Journal of Chemical Physics, Vol. 105, Issue 19 https://doi.org/10.1063/1.472621	journal	November 1996
Identification of unavoided crossings in nonadiabatic photoexcited dynamics involving multiple electronic states in polyatomic conjugated molecules Fernandez-Alberti, Sebastian; Roitberg, Adrian E.; Nelson, Tammie The Journal of Chemical Physics, Vol. 137, Issue 1 https://doi.org/10.1063/1.4732536	journal	July 2012
Nonadiabatic excited-state molecular dynamics: Treatment of electronic decoherence Nelson, Tammie; Fernandez-Alberti, Sebastian; Roitberg, Adrian E. The Journal of Chemical Physics, Vol. 138, Issue 22 https://doi.org/10.1063/1.4809568	journal	June 2013
Experimental and theoretical study of energy transfer in a chromophore triad: What makes modeling dynamics successful? Freixas, Victor M.; Nelson, Tammie; Ondarse-Alvarez, Dianelys The Journal of Chemical Physics, Vol. 153, Issue 24 https://doi.org/10.1063/5.0028126	journal	December 2020
Electronic Coherence and Collective Optical Excitations of Conjugated Molecules Mukamel, S. Science, Vol. 277, Issue 5327 https://doi.org/10.1126/science.277.5327.781	journal	August 1997
Distribution and Fate of Military Explosives and Propellants in Soil: A Review Pichtel, John Applied and Environmental Soil Science, Vol. 2012 https://doi.org/10.1155/2012/617236	journal	January 2012

Similar Records

Radiolytic degradation of dodecane substituted with common energetic functional groups

Journal Article · Mon Mar 20 00:00:00 EDT 2023 · RSC Advances · OSTI ID:1962715

Understanding Trigger Linkage Dynamics in Energetic Materials Using Mixed Picramide Nitrate Ester Explosives

Journal Article · Mon Jan 06 23:00:00 EST 2025 · Journal of Physical Chemistry Letters · OSTI ID:2506993

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
computational chemistry
degradation
energy
functional groups
molecules

Modeling Photolytic Decomposition of Energetically Functionalized Dodecanes

Citation Formats

References (45)

Similar Records

Related Subjects