The role of stereochemistry in combustion processes

Elliott, Sarah N.; Moore, III, Kevin B.; Mulvihill, Clayton R.; Copan, Andreas V.; Pratali Maffei, Luna; Klippenstein, Stephen J.

doi:10.1002/wcms.1710

The role of stereochemistry in combustion processes

Journal Article · Thu Mar 21 00:00:00 EDT 2024 · Wiley Interdisciplinary Reviews: Computational Molecular Science

DOI:https://doi.org/10.1002/wcms.1710· OSTI ID:2340970

^[1]; ^[1]; ^[2]; ^[3]; ^[4]; ^[1]

Chemical Sciences and Engineering Division Argonne National Laboratory Lemont Illinois USA
Department of Mechanical Engineering Baylor University Waco Texas USA
College of Engineering University of Georgia Athens Georgia USA, Department of Chemistry University of Georgia Athens Georgia USA
Dipartimento di Chimica, Materiali e Ingegneria Chimica “Giulio Natta” Politecnico di Milano Milano Italy

Abstract

Stereochemical effects significantly influence chemical processes, yet it is not well understood if they are a leading source of uncertainty in combustion modeling. Stereochemistry influences a combustion model (i) at the earliest stage of its construction when mapping the reaction network, (ii) in the computation of individual thermochemical and rate parameters, and (iii) in the prediction of combustion observables. The present work reviews the importance of enumerating stereochemical species and reactions at each of these steps. Further, it analyzes the separate influence of several types of stereochemistry, including geometric, optical, and fleeting transition state diastereomers. Three reaction networks serve to examine which stages of low‐temperature oxidation are most affected by stereochemistry, including the first and second oxidation of n ‐butane, the third oxidation of n ‐pentane, and the early stages of pyrolysis of 1‐ and 2‐pentene. The 149 reactions in the n ‐butane mechanism are expanded to 183 reactions when accounting for diastereomerism. Each of these 183 reactions is parameterized with ab initio kinetics computations to determine that, for the n ‐butane mechanism, the median factor of diastereomeric deviation is 3.5 at 360 K for rate constants and as high as 1.6 for mechanism reactivity, in terms of ignition delay times, as opposed to a mechanism without stereochemical expansion.

This article is categorized under:

Theoretical and Physical Chemistry > Reaction Dynamics and Kinetics

Theoretical and Physical Chemistry > Thermochemistry

Software > Simulation Methods

View Journal Article

Sponsoring Organization:: USDOE

Grant/Contract Number:: NONE; AC02-06CH11357

OSTI ID:: 2340970

Alternate ID(s):: OSTI ID: 2484290

Journal Information:: Wiley Interdisciplinary Reviews: Computational Molecular Science, Journal Name: Wiley Interdisciplinary Reviews: Computational Molecular Science Journal Issue: 2 Vol. 14; ISSN 1759-0876

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: United States

Language:: English

References (43)

Specification of Molecular Chirality Cahn, R. S.; Ingold, Christopher; Prelog, V. Angewandte Chemie International Edition in English, Vol. 5, Issue 4 https://doi.org/10.1002/anie.196603851	journal	April 1966
Implementation of Stereochemistry in Automatic Kinetic Model Generation: IMPLEMENTATION OF STEREOCHEMISTRY IN AUTOMATIC KINETIC MODEL GENERATION Vandewiele, Nick M.; Van De Vijver, Ruben; Carstensen, Hans-Heinrich International Journal of Chemical Kinetics, Vol. 48, Issue 12 https://doi.org/10.1002/kin.21030	journal	September 2016
“Third‐body” collision parameters for hydrocarbons, alcohols, and hydroperoxides and an effective internal rotor approach for estimating them Jasper, Ahren W. International Journal of Chemical Kinetics, Vol. 52, Issue 6 https://doi.org/10.1002/kin.21358	journal	April 2020
Isomer‐dependent reaction mechanisms of cyclic ether intermediates: cis ‐2,3‐dimethyloxirane and trans ‐2,3‐dimethyloxirane Doner, Anna C.; Davis, Matthew M.; Koritzke, Alanna L. International Journal of Chemical Kinetics https://doi.org/10.1002/kin.21429	journal	October 2020
Temperature dependence of the rate constants of the reactions of oxygen atoms with trans‐2‐butene, cis‐2‐butene, 2‐methylpropene, 2‐methyl‐2‐butene, and 2,3‐dimethyl‐2‐butene Biehl, H.; Bittner, J.; Bohn, B. International Journal of Chemical Kinetics, Vol. 27, Issue 3 https://doi.org/10.1002/kin.550270306	journal	March 1995
Stereochemistry of Organic Compounds Ahluwalia, V. K. https://doi.org/10.1007/978-3-030-84961-0	book	January 2022
Stereochemistry and sequence rules a proposal for modification of Cahn-Ingold-Prelog system Perdih, Marko; Razinger, Marko Tetrahedron: Asymmetry, Vol. 5, Issue 5 https://doi.org/10.1016/S0957-4166(00)86237-0	journal	May 1994
Chemistry of secondary organic aerosol: Formation and evolution of low-volatility organics in the atmosphere Kroll, Jesse H.; Seinfeld, John H. Atmospheric Environment, Vol. 42, Issue 16 https://doi.org/10.1016/j.atmosenv.2008.01.003	journal	May 2008
Genesys: Kinetic model construction using chemo-informatics Vandewiele, Nick M.; Van Geem, Kevin M.; Reyniers, Marie-Françoise Chemical Engineering Journal, Vol. 207-208 https://doi.org/10.1016/j.cej.2012.07.014	journal	October 2012
n-Butane: Ignition delay measurements at high pressure and detailed chemical kinetic simulations Healy, D.; Donato, N. S.; Aul, C. J. Combustion and Flame, Vol. 157, Issue 8 https://doi.org/10.1016/j.combustflame.2010.01.016	journal	August 2010
Understanding the antagonistic effect of methanol as a component in surrogate fuel models: A case study of methanol/n-heptane mixtures Wu, Yingtao; Panigrahy, Snehasish; Sahu, Amrit B. Combustion and Flame, Vol. 226 https://doi.org/10.1016/j.combustflame.2020.12.006	journal	April 2021
Automated identification and calculation of prompt effects in kinetic mechanisms using statistical models Pratali Maffei, Luna; Moore, Kevin B.; Georgievskii, Yuri Combustion and Flame, Vol. 257 https://doi.org/10.1016/j.combustflame.2022.112422	journal	November 2023
Systematically derived thermodynamic properties for alkane oxidation Elliott, Sarah N.; Moore, Kevin B.; Copan, Andreas V. Combustion and Flame https://doi.org/10.1016/j.combustflame.2022.112487	journal	January 2023
Diethyl ether oxidation: Revisiting the kinetics of the intramolecular hydrogen abstraction reactions of its primary and secondary peroxy radicals Duan, Yaozong; Monge-Palacios, M.; Grajales-Gonzalez, E. Fuel, Vol. 326 https://doi.org/10.1016/j.fuel.2022.125046	journal	October 2022
Detailed chemical kinetic models for the low-temperature combustion of hydrocarbons with application to gasoline and diesel fuel surrogates Battin-Leclerc, F. Progress in Energy and Combustion Science, Vol. 34, Issue 4 https://doi.org/10.1016/j.pecs.2007.10.002	journal	August 2008
Kinetics of elementary reactions in low-temperature autoignition chemistry Zádor, Judit; Taatjes, Craig A.; Fernandes, Ravi X. Progress in Energy and Combustion Science, Vol. 37, Issue 4 https://doi.org/10.1016/j.pecs.2010.06.006	journal	August 2011
Evolution, challenges and path forward for low temperature combustion engines Agarwal, Avinash Kumar; Singh, Akhilendra Pratap; Maurya, Rakesh Kumar Progress in Energy and Combustion Science, Vol. 61 https://doi.org/10.1016/j.pecs.2017.02.001	journal	July 2017
From theoretical reaction dynamics to chemical modeling of combustion Klippenstein, Stephen J. Proceedings of the Combustion Institute, Vol. 36, Issue 1 https://doi.org/10.1016/j.proci.2016.07.100	journal	January 2017
Developing detailed chemical kinetic mechanisms for fuel combustion Curran, Henry J. Proceedings of the Combustion Institute, Vol. 37, Issue 1 https://doi.org/10.1016/j.proci.2018.06.054	journal	January 2019
Automated theoretical chemical kinetics: Predicting the kinetics for the initial stages of pyrolysis Elliott, Sarah N.; Moore, Kevin B.; Copan, Andreas V. Proceedings of the Combustion Institute, Vol. 38, Issue 1 https://doi.org/10.1016/j.proci.2020.06.019	journal	January 2021
Probing O2 dependence of hydroperoxy-butyl reactions via isomer-resolved speciation Hartness, Samuel W.; Dewey, Nicholas S.; Christianson, Matthew G. Proceedings of the Combustion Institute https://doi.org/10.1016/j.proci.2022.09.066	journal	November 2022
A review on low temperature combustion engines: Performance, combustion and emission characteristics Krishnamoorthi, M.; Malayalamurthi, R.; He, Zhixia Renewable and Sustainable Energy Reviews, Vol. 116 https://doi.org/10.1016/j.rser.2019.109404	journal	December 2019
EStokTP: Electronic Structure to Temperature- and Pressure-Dependent Rate Constants—A Code for Automatically Predicting the Thermal Kinetics of Reactions Cavallotti, C.; Pelucchi, M.; Georgievskii, Y. Journal of Chemical Theory and Computation, Vol. 15, Issue 2 https://doi.org/10.1021/acs.jctc.8b00701	journal	November 2018
Diastereomers and Low-Temperature Oxidation Danilack, Aaron D.; Mulvihill, Clayton R.; Klippenstein, Stephen J. The Journal of Physical Chemistry A, Vol. 125, Issue 36 https://doi.org/10.1021/acs.jpca.1c05635	journal	September 2021
High-Accuracy Heats of Formation for Alkane Oxidation: From Small to Large via the Automated CBH-ANL Method Elliott, Sarah N.; Keçeli, Murat; Ghosh, Manik K. The Journal of Physical Chemistry A, Vol. 127, Issue 6 https://doi.org/10.1021/acs.jpca.2c07248	journal	January 2023
A Combined Experimental and Theoretical Study of the Reaction OH + 2-Butene in the 400–800 K Temperature Range Antonov, Ivan O.; Kwok, Justin; Zádor, Judit The Journal of Physical Chemistry A, Vol. 119, Issue 28 https://doi.org/10.1021/acs.jpca.5b01012	journal	February 2015
High-Pressure Limit Rate Rules for α-H Isomerization of Hydroperoxyalkylperoxy Radicals Mohamed, Samah Y.; Davis, Alexander C.; Al Rashidi, Mariam J. The Journal of Physical Chemistry A, Vol. 122, Issue 14 https://doi.org/10.1021/acs.jpca.7b11955	journal	March 2018
Comparison of the Kinetics of O(3P) Reactions with the Four Butenes over Wide Temperature Ranges Adusei, George Yaw; Fontijn, Arthur The Journal of Physical Chemistry, Vol. 98, Issue 14 https://doi.org/10.1021/j100065a031	journal	April 1994
Thermochemical Studies of Epoxides and Related Compounds Morgan, Kathleen M.; Ellis, Jamie A.; Lee, Joseph The Journal of Organic Chemistry, Vol. 78, Issue 9 https://doi.org/10.1021/jo4002867	journal	April 2013
Reactions of OH with Butene Isomers: Measurements of the Overall Rates and a Theoretical Study Vasu, Subith S.; Huynh, Lam K.; Davidson, David F. The Journal of Physical Chemistry A, Vol. 115, Issue 12 https://doi.org/10.1021/jp112294h	journal	March 2011
Reformulation and Solution of the Master Equation for Multiple-Well Chemical Reactions Georgievskii, Yuri; Miller, James A.; Burke, Michael P. The Journal of Physical Chemistry A, Vol. 117, Issue 46 https://doi.org/10.1021/jp4060704	journal	May 2013
Stereoisomer-dependent unimolecular kinetics of 2,4-dimethyloxetanyl peroxy radicals Doner, Anna C.; Zádor, Judit; Rotavera, Brandon Faraday Discussions, Vol. 238 https://doi.org/10.1039/D2FD00029F	journal	January 2022
Unimolecular phase space theory rates by inversion of angular momentum-conserved partition function Forst, Wendell Physical Chemistry Chemical Physics, Vol. 1, Issue 6 https://doi.org/10.1039/a808671k	journal	January 1999
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections Chai, Jeng-Da; Head-Gordon, Martin Physical Chemistry Chemical Physics, Vol. 10, Issue 44 https://doi.org/10.1039/b810189b	journal	January 2008
Kinetics, products, and mechanisms of secondary organic aerosol formation Ziemann, Paul J.; Atkinson, Roger Chemical Society Reviews, Vol. 41, Issue 19 https://doi.org/10.1039/c2cs35122f	journal	January 2012
Collisional Energy Transfer. Thermal Unimolecular Systems in the Low‐Pressure Region Tardy, D. C.; Rabinovitch, B. S. The Journal of Chemical Physics, Vol. 45, Issue 10 https://doi.org/10.1063/1.1727392	journal	November 1966
Simplified CCSD(T)-F12 methods: Theory and benchmarks Knizia, Gerald; Adler, Thomas B.; Werner, Hans-Joachim The Journal of Chemical Physics, Vol. 130, Issue 5 https://doi.org/10.1063/1.3054300	journal	February 2009
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements Francl, Michelle M.; Pietro, William J.; Hehre, Warren J. The Journal of Chemical Physics, Vol. 77, Issue 7, p. 3654-3665 https://doi.org/10.1063/1.444267	journal	October 1982
Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen Dunning, Thom H. The Journal of Chemical Physics, Vol. 90, Issue 2 https://doi.org/10.1063/1.456153	journal	January 1989
Variational optimizations in the Rice–Ramsperger–Kassel–Marcus theory calculations for unimolecular dissociations with no reverse barrier Klippenstein, Stephen J. The Journal of Chemical Physics, Vol. 96, Issue 1 https://doi.org/10.1063/1.462472	journal	January 1992
Getting started Oliveira, Suely; Stewart, David Building Proofs https://doi.org/10.1142/9789814641319_0001	book	May 2015
InChI, the IUPAC International Chemical Identifier Heller, Stephen R.; McNaught, Alan; Pletnev, Igor Journal of Cheminformatics, Vol. 7, Issue 1 https://doi.org/10.1186/s13321-015-0068-4	journal	May 2015

Similar Records

Diastereomers and Low-Temperature Oxidation

Journal Article · Wed Sep 01 00:00:00 EDT 2021 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory · OSTI ID:1854512

Stereoisomer-dependent unimolecular kinetics of 2,4-dimethyloxetanyl peroxy radicals

Journal Article · Wed Apr 20 00:00:00 EDT 2022 · Faraday Discussions · OSTI ID:1871974

The role of stereochemistry in combustion processes

Citation Formats

References (43)

Similar Records

Related Subjects