Unimolecular Reaction Pathways of a γ-Ketohydroperoxide from Combined Application of Automated Reaction Discovery Methods

Grambow, Colin A.; Jamal, Adeel; Li, Yi -Pei; Green, William H.; Zador, Judit; Suleimanov, Yury V.

doi:10.1021/jacs.7b11009

Unimolecular Reaction Pathways of a γ-Ketohydroperoxide from Combined Application of Automated Reaction Discovery Methods

Journal Article · Fri Dec 22 00:00:00 EST 2017 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.7b11009· OSTI ID:1421464

^[1]; ^[2]; Li, Yi -Pei ^[2]; ^[2]; ^[3]; Suleimanov, Yury V. ^[4]

Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States); Masschusetts Institute of Technology
Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)
Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Computation-based Science and Technology Research Center, Nicosia (Cyprus)

Ketohydroperoxides are important in liquid-phase autoxidation and in gas-phase partial oxidation and pre-ignition chemistry, but because of their low concentration, instability, and various analytical chemistry limitations, it has been challenging to experimentally determine their reactivity, and only a few pathways are known. In the present work, 75 elementary-step unimolecular reactions of the simplest γ-ketohydroperoxide, 3-hydroperoxypropanal, were discovered by a combination of density functional theory with several automated transition-state search algorithms: the Berny algorithm coupled with the freezing string method, single- and double-ended growing string methods, the heuristic KinBot algorithm, and the single-component artificial force induced reaction method (SC-AFIR). The present joint approach significantly outperforms previous manual and automated transition-state searches – 68 of the reactions of γ-ketohydroperoxide discovered here were previously unknown and completely unexpected. All of the methods found the lowest-energy transition state, which corresponds to the first step of the Korcek mechanism, but each algorithm except for SC-AFIR detected several reactions not found by any of the other methods. We show that the low-barrier chemical reactions involve promising new chemistry that may be relevant in atmospheric and combustion systems. Our study highlights the complexity of chemical space exploration and the advantage of combined application of several approaches. Altogether, the present work demonstrates both the power and the weaknesses of existing fully automated approaches for reaction discovery which suggest possible directions for further method development and assessment in order to enable reliable discovery of all important reactions of any specified reactant(s).

View Accepted Manuscript (DOE)

Research Organization:: Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States); Sandia National Lab. (SNL-CA), Livermore, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-05CH11231; AC04-94AL85000

OSTI ID:: 1421464

Alternate ID(s):: OSTI ID: 1473944

Report Number(s):: SAND--2018-9927J

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 3 Vol. 140; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (78)

Using redundant internal coordinates to optimize equilibrium geometries and transition states Peng, Chunyang; Ayala, Philippe Y.; Schlegel, H. Bernhard Journal of Computational Chemistry, Vol. 17, Issue 1 https://doi.org/10.1002/(SICI)1096-987X(19960115)17:1<49::AID-JCC5>3.0.CO;2-0	journal	January 1996
Heterogeneous Catalysis Schlögl, Robert Angewandte Chemie International Edition, Vol. 54, Issue 11 https://doi.org/10.1002/anie.201410738	journal	February 2015
Gas-Phase Experiments Aimed at Probing the Existence of the Elusive Water Oxide Molecule Schröder, Detlef; Schalley, Christoph A.; Schwarz, Helmut Chemistry - A European Journal, Vol. 2, Issue 10 https://doi.org/10.1002/chem.19960021009	journal	October 1996
Exploring transition state structures for intramolecular pathways by the artificial force induced reaction method Maeda, Satoshi; Taketsugu, Tetsuya; Morokuma, Keiji Journal of Computational Chemistry, Vol. 35, Issue 2 https://doi.org/10.1002/jcc.23481	journal	November 2013
Single-ended transition state finding with the growing string method Zimmerman, Paul M. Journal of Computational Chemistry, Vol. 36, Issue 9 https://doi.org/10.1002/jcc.23833	journal	January 2015
Optimization of equilibrium geometries and transition structures Schlegel, H. Bernhard Journal of Computational Chemistry, Vol. 3, Issue 2 https://doi.org/10.1002/jcc.540030212	journal	July 1982
Artificial Force Induced Reaction (AFIR) Method for Exploring Quantum Chemical Potential Energy Surfaces Maeda, Satoshi; Harabuchi, Yu; Takagi, Makito The Chemical Record, Vol. 16, Issue 5 https://doi.org/10.1002/tcr.201600043	journal	June 2016
Vibration Measurement and Monitoring Schlegel, V. Dynamics of Rotors https://doi.org/10.1007/978-3-7091-2812-1_13	book	January 1984
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Zhao, Yan; Truhlar, Donald G. Theoretical Chemistry Accounts, Vol. 120, Issue 1-3 https://doi.org/10.1007/s00214-007-0310-x	journal	July 2007
Conjugate peak refinement: an algorithm for finding reaction paths and accurate transition states in systems with many degrees of freedom Fischer, Stefan; Karplus, Martin Chemical Physics Letters, Vol. 194, Issue 3 https://doi.org/10.1016/0009-2614(92)85543-J	journal	June 1992
Challenges and opportunities for molecule-based management of chemical processes Van de Vijver, Ruben; Devocht, Brigitte R.; Van Geem, Kevin M. Current Opinion in Chemical Engineering, Vol. 13 https://doi.org/10.1016/j.coche.2016.09.006	journal	August 2016
Chemical mechanism for high temperature combustion of engine relevant fuels with emphasis on soot precursors Blanquart, G.; Pepiot-Desjardins, P.; Pitsch, H. Combustion and Flame, Vol. 156, Issue 3 https://doi.org/10.1016/j.combustflame.2008.12.007	journal	March 2009
Design and implementation of a next-generation software interface for on-the-fly quantum and force field calculations in automated reaction mechanism generation Magoon, Gregory R.; Green, William H. Computers & Chemical Engineering, Vol. 52 https://doi.org/10.1016/j.compchemeng.2012.11.009	journal	May 2013
MSTor: A program for calculating partition functions, free energies, enthalpies, entropies, and heat capacities of complex molecules including torsional anharmonicity Zheng, Jingjing; Mielke, Steven L.; Clarkson, Kenneth L. Computer Physics Communications, Vol. 183, Issue 8 https://doi.org/10.1016/j.cpc.2012.03.007	journal	August 2012
MSTor version 2013: A new version of the computer code for the multi-structural torsional anharmonicity, now with a coupled torsional potential Zheng, Jingjing; Meana-Pañeda, Rubén; Truhlar, Donald G. Computer Physics Communications, Vol. 184, Issue 8 https://doi.org/10.1016/j.cpc.2013.03.011	journal	August 2013
Reaction Mechanism Generator: Automatic construction of chemical kinetic mechanisms Gao, Connie W.; Allen, Joshua W.; Green, William H. Computer Physics Communications, Vol. 203 https://doi.org/10.1016/j.cpc.2016.02.013	journal	June 2016
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
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
Computational Catalysis Using the Artificial Force Induced Reaction Method Sameera, W. M. C.; Maeda, Satoshi; Morokuma, Keiji Accounts of Chemical Research, Vol. 49, Issue 4 https://doi.org/10.1021/acs.accounts.6b00023	journal	March 2016
Catalysts by Design: The Power of Theory Hammes-Schiffer, Sharon Accounts of Chemical Research, Vol. 50, Issue 3 https://doi.org/10.1021/acs.accounts.6b00555	journal	March 2017
A Holy Grail in Chemistry: Computational Catalyst Design: Feasible or Fiction? Poree, Carl; Schoenebeck, Franziska Accounts of Chemical Research, Vol. 50, Issue 3 https://doi.org/10.1021/acs.accounts.6b00606	journal	March 2017
Ab Initio Reactive Computer Aided Molecular Design Martínez, Todd J. Accounts of Chemical Research, Vol. 50, Issue 3 https://doi.org/10.1021/acs.accounts.7b00010	journal	March 2017
Automated Discovery of Elementary Chemical Reaction Steps Using Freezing String and Berny Optimization Methods Suleimanov, Yury V.; Green, William H. Journal of Chemical Theory and Computation, Vol. 11, Issue 9 https://doi.org/10.1021/acs.jctc.5b00407	journal	August 2015
Heuristics-Guided Exploration of Reaction Mechanisms Bergeler, Maike; Simm, Gregor N.; Proppe, Jonny Journal of Chemical Theory and Computation, Vol. 11, Issue 12 https://doi.org/10.1021/acs.jctc.5b00866	journal	November 2015
Automatic Reaction Pathway Search via Combined Molecular Dynamics and Coordinate Driving Method Yang, Manyi; Zou, Jingxiang; Wang, Guoqiang The Journal of Physical Chemistry A, Vol. 121, Issue 6 https://doi.org/10.1021/acs.jpca.6b12195	journal	February 2017
Neural Networks for the Prediction of Organic Chemistry Reactions Wei, Jennifer N.; Duvenaud, David; Aspuru-Guzik, Alán ACS Central Science, Vol. 2, Issue 10 https://doi.org/10.1021/acscentsci.6b00219	journal	October 2016
Theoretical Chemical Kinetics in Tropospheric Chemistry: Methodologies and Applications Vereecken, Luc; Glowacki, David R.; Pilling, Michael J. Chemical Reviews, Vol. 115, Issue 10 https://doi.org/10.1021/cr500488p	journal	February 2015
Reliable Transition State Searches Integrated with the Growing String Method Zimmerman, Paul Journal of Chemical Theory and Computation, Vol. 9, Issue 7 https://doi.org/10.1021/ct400319w	journal	June 2013
Atmospheric Chemistry of Enols: A Theoretical Study of the Vinyl Alcohol + OH + O ₂ Reaction Mechanism So, Sui; Wille, Uta; da Silva, Gabriel Environmental Science & Technology, Vol. 48, Issue 12 https://doi.org/10.1021/es500319q	journal	May 2014
Atmospheric Chemistry of Acetylacetone Zhou, Shouming; Barnes, Ian; Zhu, Tong Environmental Science & Technology, Vol. 42, Issue 21 https://doi.org/10.1021/es8010282	journal	September 2008
Nature of the transition structure for oxygen atom transfer from a hydroperoxide. Theoretical comparison between water oxide and ammonia oxide Bach, Robert D.; Owensby, Amy L.; Gonzalez, Carlos Journal of the American Chemical Society, Vol. 113, Issue 16 https://doi.org/10.1021/ja00016a012	journal	July 1991
Aspects of the reaction mechanism of ethane combustion. Conformations of the ethylperoxy radical Quelch, Geoffrey E.; Gallo, Mary M.; Schaefer, Henry F. Journal of the American Chemical Society, Vol. 114, Issue 21 https://doi.org/10.1021/ja00047a039	journal	October 1992
A theoretical model for the orientation of carbene insertion into saturated hydrocarbons and the origin of the activation barrier Bach, Robert D.; Su, Ming Der; Aldabbagh, Ehab Journal of the American Chemical Society, Vol. 115, Issue 22 https://doi.org/10.1021/ja00075a045	journal	November 1993
Liquid-phase autoxidation of organic compounds at elevated temperatures. 2. Kinetics and mechanisms of the formation of cleavage products in n-hexadecane autoxidation Jensen, R. K.; Korcek, S.; Mahoney, L. R. Journal of the American Chemical Society, Vol. 103, Issue 7 https://doi.org/10.1021/ja00397a026	journal	April 1981
Liquid-phase autoxidation of organic compounds at elevated temperatures. 1. The stirred flow reactor technique and analysis of primary products from n-hexadecane autoxidation at 120-180.degree.C Jensen, R. K.; Korcek, S.; Mahoney, L. R. Journal of the American Chemical Society, Vol. 101, Issue 25 https://doi.org/10.1021/ja00519a018	journal	December 1979
New Pathways for Formation of Acids and Carbonyl Products in Low-Temperature Oxidation: The Korcek Decomposition of γ-Ketohydroperoxides Jalan, Amrit; Alecu, Ionut M.; Meana-Pañeda, Rubén Journal of the American Chemical Society, Vol. 135, Issue 30 https://doi.org/10.1021/ja4034439	journal	July 2013
Direct Observation of the Gas-Phase Criegee Intermediate (CH ₂ OO) Taatjes, Craig A.; Meloni, Giovanni; Selby, Talitha M. Journal of the American Chemical Society, Vol. 130, Issue 36 https://doi.org/10.1021/ja804165q	journal	September 2008
Studies of the Mechanism and Origins of Enantioselectivity for the Chiral Phosphoric Acid-Catalyzed Stereoselective Spiroketalization Reactions Khomutnyk, Yaroslav Ya.; Argüelles, Alonso J.; Winschel, Grace A. Journal of the American Chemical Society, Vol. 138, Issue 1 https://doi.org/10.1021/jacs.5b12528	journal	December 2015
Kinetics of the Gas-Phase Reactions of Alcohols, Aldehydes, Carboxylic Acids, and Water with the C13 Stabilized Criegee Intermediate Formed from Ozonolysis of 1-Tetradecene Tobias, Herbert J.; Ziemann, Paul J. The Journal of Physical Chemistry A, Vol. 105, Issue 25 https://doi.org/10.1021/jp004631r	journal	June 2001
Hybrid Density Functional Theory Predictions of Low-Temperature Dimethyl Ether Combustion Pathways. II. Chain-Branching Energetics and Possible Role of the Criegee Intermediate Andersen, Amity; Carter, Emily A. The Journal of Physical Chemistry A, Vol. 107, Issue 44 https://doi.org/10.1021/jp035423c	journal	November 2003
Ab Initio and Direct Dynamics Studies of the Reaction of Singlet Methylene with Acetylene and the Lifetime of the Cyclopropene Complex Yu, Hua-Gen; Muckerman, James T. The Journal of Physical Chemistry A, Vol. 109, Issue 9 https://doi.org/10.1021/jp045049w	journal	February 2005
Pathways and Rate Coefficients for the Decomposition of Vinoxy and Acetyl Radicals Senosiain, Juan P.; Klippenstein, Stephen J.; Miller, James A. The Journal of Physical Chemistry A, Vol. 110, Issue 17 https://doi.org/10.1021/jp054934r	journal	May 2006
Mindless Chemistry Bera, Partha P.; Sattelmeyer, Kurt W.; Saunders, Martin The Journal of Physical Chemistry A, Vol. 110, Issue 13 https://doi.org/10.1021/jp057107z	journal	April 2006
Multipath Variational Transition State Theory: Rate Constant of the 1,4-Hydrogen Shift Isomerization of the 2-Cyclohexylethyl Radical Yu, Tao; Zheng, Jingjing; Truhlar, Donald G. The Journal of Physical Chemistry A, Vol. 116, Issue 1 https://doi.org/10.1021/jp209146b	journal	December 2011
Performance of M06, M06-2X, and M06-HF Density Functionals for Conformationally Flexible Anionic Clusters: M06 Functionals Perform Better than B3LYP for a Model System with Dispersion and Ionic Hydrogen-Bonding Interactions Walker, Martin; Harvey, Andrew J. A.; Sen, Ananya The Journal of Physical Chemistry A, Vol. 117, Issue 47 https://doi.org/10.1021/jp408166m	journal	November 2013
Direct Kinetic Measurements of Reactions between the Simplest Criegee Intermediate CH ₂ OO and Alkenes Buras, Zachary J.; Elsamra, Rehab M. I.; Jalan, Amrit The Journal of Physical Chemistry A, Vol. 118, Issue 11 https://doi.org/10.1021/jp4118985	journal	March 2014
Ether Oxides: A New Class of Stable Ylides? A Theoretical Study of Methanol Oxide and Dimethyl Ether Oxide Schalley, Christoph A.; Harvey, Jeremy N.; Schröder, Detlef The Journal of Physical Chemistry A, Vol. 102, Issue 6 https://doi.org/10.1021/jp972986d	journal	February 1998
Phototautomerization of Acetaldehyde to Vinyl Alcohol: A Primary Process in UV-Irradiated Acetaldehyde from 295 to 335 nm Clubb, Alexander E.; Jordan, Meredith J. T.; Kable, S. H. The Journal of Physical Chemistry Letters, Vol. 3, Issue 23 https://doi.org/10.1021/jz301701x	journal	November 2012
Unconventional Peroxy Chemistry in Alcohol Oxidation: The Water Elimination Pathway Welz, Oliver; Klippenstein, Stephen J.; Harding, Lawrence B. The Journal of Physical Chemistry Letters, Vol. 4, Issue 3 https://doi.org/10.1021/jz302004w	journal	January 2013
Direct Determination of the Simplest Criegee Intermediate (CH ₂ OO) Self Reaction Rate Buras, Zachary J.; Elsamra, Rehab M. I.; Green, William H. The Journal of Physical Chemistry Letters, Vol. 5, Issue 13 https://doi.org/10.1021/jz5008406	journal	June 2014
Molecular hydrogen in the troposphere: Global distribution and budget Novelli, Paul C.; Lang, Patricia M.; Masarie, Kenneth A. Journal of Geophysical Research: Atmospheres, Vol. 104, Issue D23 https://doi.org/10.1029/1999JD900788	journal	December 1999
Iron(III)-catalysed carbonyl–olefin metathesis Ludwig, Jacob R.; Zimmerman, Paul M.; Gianino, Joseph B. Nature, Vol. 533, Issue 7603 https://doi.org/10.1038/nature17432	journal	April 2016
Near-threshold H/D exchange in CD3CHO photodissociation Heazlewood, Brianna R.; Maccarone, Alan T.; Andrews, Duncan U. Nature Chemistry, Vol. 3, Issue 6 https://doi.org/10.1038/nchem.1052	journal	May 2011
Discovering chemistry with an ab initio nanoreactor Wang, Lee-Ping; Titov, Alexey; McGibbon, Robert Nature Chemistry, Vol. 6, Issue 12 https://doi.org/10.1038/nchem.2099	journal	November 2014
Theoretical study of the reactions of Criegee intermediates with ozone, alkylhydroperoxides, and carbon monoxide Vereecken, L.; Rickard, A. R.; Newland, M. J. Physical Chemistry Chemical Physics, Vol. 17, Issue 37 https://doi.org/10.1039/C5CP03862F	journal	January 2015
Transition state geometry prediction using molecular group contributions Bhoorasingh, Pierre L.; West, Richard H. Physical Chemistry Chemical Physics, Vol. 17, Issue 48 https://doi.org/10.1039/C5CP04706D	journal	January 2015
Finding reaction mechanisms, intuitive or otherwise Dewyer, Amanda L.; Zimmerman, Paul M. Organic & Biomolecular Chemistry, Vol. 15, Issue 3 https://doi.org/10.1039/C6OB02183B	journal	January 2017
The reaction of Criegee intermediates with acids and enols Vereecken, L. Physical Chemistry Chemical Physics, Vol. 19, Issue 42 https://doi.org/10.1039/C7CP05132H	journal	January 2017
Unimolecular decay strongly limits the atmospheric impact of Criegee intermediates Vereecken, L.; Novelli, A.; Taraborrelli, D. Physical Chemistry Chemical Physics, Vol. 19, Issue 47 https://doi.org/10.1039/C7CP05541B	journal	January 2017
Time-dependent master equation simulation of complex elementary reactions in combustion: Application to the reaction of 1CH2 with C2H2 from 300â€“2000 K Frankcombe, Terry J.; Smith, Sean C. Faraday Discussions, Vol. 119, Issue 1 https://doi.org/10.1039/b102562g	journal	September 2001
Multi-structural variational transition state theory. Kinetics of the 1,4-hydrogen shift isomerization of the pentyl radical with torsional anharmonicity Yu, Tao; Zheng, Jingjing; Truhlar, Donald G. Chemical Science, Vol. 2, Issue 11 https://doi.org/10.1039/c1sc00225b	journal	January 2011
Direct measurement of Criegee intermediate (CH2OO) reactions with acetone, acetaldehyde, and hexafluoroacetone Taatjes, Craig A.; Welz, Oliver; Eskola, Arkke J. Physical Chemistry Chemical Physics, Vol. 14, Issue 30 https://doi.org/10.1039/c2cp40294g	journal	January 2012
Theoretical studies of atmospheric reaction mechanisms in the troposphere Vereecken, Luc; Francisco, Joseph S. Chemical Society Reviews, Vol. 41, Issue 19 https://doi.org/10.1039/c2cs35070j	journal	January 2012
Tropospheric OH and HO2 radicals: field measurements and model comparisons Stone, Daniel; Whalley, Lisa K.; Heard, Dwayne E. Chemical Society Reviews, Vol. 41, Issue 19 https://doi.org/10.1039/c2cs35140d	journal	January 2012
Chemically activated formation of organic acids in reactions of the Criegee intermediate with aldehydes and ketones Jalan, Amrit; Allen, Joshua W.; Green, William H. Physical Chemistry Chemical Physics, Vol. 15, Issue 39 https://doi.org/10.1039/c3cp52598h	journal	January 2013
Improved tangent estimate in the nudged elastic band method for finding minimum energy paths and saddle points Henkelman, Graeme; Jónsson, Hannes The Journal of Chemical Physics, Vol. 113, Issue 22 https://doi.org/10.1063/1.1323224	journal	December 2000
A climbing image nudged elastic band method for finding saddle points and minimum energy paths Henkelman, Graeme; Uberuaga, Blas P.; Jónsson, Hannes The Journal of Chemical Physics, Vol. 113, Issue 22, p. 9901-9904 https://doi.org/10.1063/1.1329672	journal	December 2000
Efficient exploration of reaction paths via a freezing string method Behn, Andrew; Zimmerman, Paul M.; Bell, Alexis T. The Journal of Chemical Physics, Vol. 135, Issue 22 https://doi.org/10.1063/1.3664901	journal	December 2011
Ridge method for finding saddle points on potential energy surfaces Ionova, Irina V.; Carter, Emily A. The Journal of Chemical Physics, Vol. 98, Issue 8 https://doi.org/10.1063/1.465100	journal	April 1993
Growing string method with interpolation and optimization in internal coordinates: Method and examples Zimmerman, Paul M. The Journal of Chemical Physics, Vol. 138, Issue 18 https://doi.org/10.1063/1.4804162	journal	May 2013
Escaping free-energy minima Laio, A.; Parrinello, M. Proceedings of the National Academy of Sciences, Vol. 99, Issue 20 https://doi.org/10.1073/pnas.202427399	journal	September 2002
Enols Are Common Intermediates in Hydrocarbon Oxidation Taatjes, C. A. Science, Vol. 308, Issue 5730 https://doi.org/10.1126/science.1112532	journal	June 2005
Direct Kinetic Measurements of Criegee Intermediate (CH2OO) Formed by Reaction of CH2I with O2 Welz, O.; Savee, J. D.; Osborn, D. L. Science, Vol. 335, Issue 6065 https://doi.org/10.1126/science.1213229	journal	January 2012
Photo-Tautomerization of Acetaldehyde to Vinyl Alcohol: A Potential Route to Tropospheric Acids Andrews, D. U.; Heazlewood, B. R.; Maccarone, A. T. Science, Vol. 337, Issue 6099 https://doi.org/10.1126/science.1220712	journal	August 2012
Direct Measurements of Conformer-Dependent Reactivity of the Criegee Intermediate CH3CHOO Taatjes, C. A.; Welz, O.; Eskola, A. J. Science, Vol. 340, Issue 6129 https://doi.org/10.1126/science.1234689	journal	April 2013
Unraveling Reaction Pathways and Specifying Reaction Kinetics for Complex Systems Vinu, R.; Broadbelt, Linda J. Annual Review of Chemical and Biomolecular Engineering, Vol. 3, Issue 1 https://doi.org/10.1146/annurev-chembioeng-062011-081108	journal	July 2012
Open Babel: An open chemical toolbox O'Boyle, Noel M.; Banck, Michael; James, Craig A. Journal of Cheminformatics, Vol. 3, Issue 1 https://doi.org/10.1186/1758-2946-3-33	journal	October 2011
Estimating the atmospheric concentration of Criegee intermediates and their possible interference in a FAGE-LIF instrument Novelli, Anna; Hens, Korbinian; Tatum Ernest, Cheryl Atmospheric Chemistry and Physics, Vol. 17, Issue 12 https://doi.org/10.5194/acp-17-7807-2017	journal	January 2017

Cited By (4)

The Exploration of Chemical Reaction Networks Unsleber, Jan P.; Reiher, Markus Annual Review of Physical Chemistry, Vol. 71, Issue 1 https://doi.org/10.1146/annurev-physchem-071119-040123	journal	April 2020
Automated reaction path searches for spin-forbidden reactions: Automated Reaction Path Searches Takayanagi, Toshiyuki; Nakatomi, Taiki Journal of Computational Chemistry, Vol. 39, Issue 19 https://doi.org/10.1002/jcc.25202	journal	March 2018
Thermochemistry of the smallest QOOH radical from the roaming fragmentation of energy selected methyl hydroperoxide ions Covert, Kyle J.; Voronova, Krisztina; Torma, Krisztián G. Physical Chemistry Chemical Physics, Vol. 20, Issue 32 https://doi.org/10.1039/c8cp03168a	journal	January 2018
Theoretical study of sensitive reactions in phenol decomposition Pratali Maffei, Luna; Pelucchi, Matteo; Faravelli, Tiziano Reaction Chemistry & Engineering, Vol. 5, Issue 3 https://doi.org/10.1039/c9re00418a	journal	January 2020