Initial-site characterization of hydrogen migration following strong-field double-ionization of ethanol

Severt, Travis; Weckwerth, Eleanor; Kaderiya, Balram; Feizollah, Peyman; Jochim, Bethany; Borne, Kurtis; Ziaee, Farzaneh; P, Kanaka Raju; Carnes, Kevin D.; Dantus, Marcos; Rolles, Daniel; Rudenko, Artem; Wells, Eric; Ben-Itzhak, Itzik

doi:10.1038/s41467-023-44311-x

Title: Initial-site characterization of hydrogen migration following strong-field double-ionization of ethanol

Journal Article · Tue Jan 02 00:00:00 EST 2024 · Nature Communications

DOI:https://doi.org/10.1038/s41467-023-44311-x· OSTI ID:2274867

Severt, Travis;

; Kaderiya, Balram;

;

; Borne, Kurtis; Ziaee, Farzaneh;

;

; Dantus, Marcos;

;

Abstract An essential problem in photochemistry is understanding the coupling of electronic and nuclear dynamics in molecules, which manifests in processes such as hydrogen migration. Measurements of hydrogen migration in molecules that have more than two equivalent hydrogen sites, however, produce data that is difficult to compare with calculations because the initial hydrogen site is unknown. We demonstrate that coincidence ion-imaging measurements of a few deuterium-tagged isotopologues of ethanol can determine the contribution of each initial-site composition to hydrogen-rich fragments following strong-field double ionization. These site-specific probabilities produce benchmarks for calculations and answer outstanding questions about photofragmentation of ethanol dications; e.g., establishing that the central two hydrogen atoms are 15 times more likely to abstract the hydroxyl proton than a methyl-group proton to form H $$$${}_{3}^{+}$$$$ $_{3}^{+}$ and that hydrogen scrambling, involving the exchange of hydrogen between different sites, is important in H ₂ O ⁺ formation. The technique extends to dynamic variables and could, in principle, be applied to larger non-cyclic hydrocarbons.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: FG02-86ER13491; FG02-09ER16115; SISGR (DE-SC0002325)

OSTI ID:: 2274867

Journal Information:: Nature Communications, Journal Name: Nature Communications Vol. 15 Journal Issue: 1; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United Kingdom

Language:: English

References (63)

Ultrafast Roaming Mechanisms in Ethanol Probed by Intense Extreme Ultraviolet Free-Electron Laser Radiation: Electron Transfer versus Proton Transfer Wang, Enliang; Kling, Nora G.; LaForge, Aaron C. The Journal of Physical Chemistry Letters, Vol. 14, Issue 18 https://doi.org/10.1021/acs.jpclett.2c03764	journal	May 2023
Formation of H₃O⁺ in the Ionization and Fragmentation of Ethanol Induced by Electron Beam Irradiation Ma, Chao; Zhou, Jiaqi; Wang, Enliang Laser and Particle Beams, Vol. 2021 https://doi.org/10.1155/2021/6616439	journal	January 2021
Orbiting resonances in formaldehyde reveal coupling of roaming, radical, and molecular channels Foley, Casey D.; Xie, Changjian; Guo, Hua Science, Vol. 374, Issue 6571 https://doi.org/10.1126/science.abk0634	journal	November 2021
The Roaming Atom: Straying from the Reaction Path in Formaldehyde Decomposition Townsend, D. Science, Vol. 306, Issue 5699 https://doi.org/10.1126/science.1104386	journal	November 2004
Ultrafast Proton Transfer Dynamics on the Repulsive Potential of the Ethanol Dication: Roaming-Mediated Isomerization versus Coulomb Explosion Wang, Enliang; Shan, Xu; Chen, Lei The Journal of Physical Chemistry A, Vol. 124, Issue 14 https://doi.org/10.1021/acs.jpca.0c02074	journal	March 2020
Ab Initio Nonadiabatic Quantum Molecular Dynamics Curchod, Basile F. E.; Martínez, Todd J. Chemical Reviews, Vol. 118, Issue 7 https://doi.org/10.1021/acs.chemrev.7b00423	journal	February 2018
Formation of H ₃ O ⁺ from alcohols and ethers induced by intense laser fields Shirota, Tatsuro; Mano, Narutoshi; Tsuge, Masashi Rapid Communications in Mass Spectrometry, Vol. 24, Issue 5 https://doi.org/10.1002/rcm.4438	journal	March 2010
NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist Fulmer, Gregory R.; Miller, Alexander J. M.; Sherden, Nathaniel H. Organometallics, Vol. 29, Issue 9 https://doi.org/10.1021/om100106e	journal	May 2010
Delineation of .alpha.-helical domains in deuteriated Staphylococcal nuclease by 2D NOE NMR spectroscopy Torchia, Dennis A.; Sparks, Steven W.; Bax, Ad. Journal of the American Chemical Society, Vol. 110, Issue 7 https://doi.org/10.1021/ja00215a063	journal	March 1988
Mechanism and Energetics of Intramolecular Hydrogen Transfer in Amide and Peptide Radicals and Cation-Radicals Tureček, František; Syrstad, Erik A. Journal of the American Chemical Society, Vol. 125, Issue 11 https://doi.org/10.1021/ja021162t	journal	March 2003
Formation of H3+ from ethane dication induced by electron impact Zhang, Yu; Ren, Baihui; Yang, Chuan-Lu Communications Chemistry, Vol. 3, Issue 1 https://doi.org/10.1038/s42004-020-00415-9	journal	November 2020
Mixed quantum–classical dynamics Tully, John C. Faraday Discussions, Vol. 110 https://doi.org/10.1039/a801824c	journal	January 1998
Metastable decomposition and hydrogen migration of ethane dication produced in an intense femtosecond near-infrared laser field Hoshina, Kennosuke; Kawamura, Haruna; Tsuge, Masashi The Journal of Chemical Physics, Vol. 134, Issue 6 https://doi.org/10.1063/1.3549137	journal	February 2011
Sequential mechanism in H₃⁺ formation dynamics on the ethanol dication Gope, Krishnendu; Bittner, Dror M.; Strasser, Daniel Physical Chemistry Chemical Physics, Vol. 25, Issue 9 https://doi.org/10.1039/D2CP03632K	journal	January 2023
Roaming reactions: The third way Bowman, Joel M.; Suits, Arthur G. Physics Today, Vol. 64, Issue 11 https://doi.org/10.1063/PT.3.1330	journal	November 2011
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
Strong-field control of H3+ production from methanol dications: Selecting between local and extended formation mechanisms Iwamoto, Naoki; Schwartz, Charles J.; Jochim, Bethany The Journal of Chemical Physics, Vol. 152, Issue 5 https://doi.org/10.1063/1.5129946	journal	February 2020
Infrared Photoactivation Reduces Peptide Folding and Hydrogen-Atom Migration following ETD Tandem Mass Spectrometry Ledvina, Aaron R.; McAlister, Graeme C.; Gardner, Myles W. Angewandte Chemie International Edition, Vol. 48, Issue 45 https://doi.org/10.1002/anie.200903557	journal	October 2009
Emerging Laser Technologies for High-Power and Ultrafast Science Légaré, François https://doi.org/10.1088/978-0-7503-2536-3	book	July 2021
Pressure-dependent rate rules for intramolecular H-migration reactions of normal-alkyl cyclohexylperoxy radicals Yao, XiaoXia; Wang, JingBo; Yao, Qian Combustion and Flame, Vol. 204 https://doi.org/10.1016/j.combustflame.2019.03.011	journal	June 2019
Recoil-ion momentum spectroscopy Ullrich, J.; Moshammer, R.; Dörner, R. Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 30, Issue 13 https://doi.org/10.1088/0953-4075/30/13/006	journal	July 1997
Theories and simulations of roaming Bowman, Joel M.; Houston, Paul L. Chemical Society Reviews, Vol. 46, Issue 24 https://doi.org/10.1039/C7CS00578D	journal	January 2017
Two-body Coulomb explosion in methylacetylene in intense laser fields: double proton migration and proton/deuteron exchange Okino, Tomoya; Watanabe, Anri; Xu, Huailiang Physical Chemistry Chemical Physics, Vol. 14, Issue 12 https://doi.org/10.1039/c2cp23880b	journal	January 2012
Studies of H+, H+2, and H+3 dissociative ionization fragments from methane, ethane, methanol, ethanol, and some deuterated methanols using electron-impact excitation and a time-of-flight method incorporating mass analysis Burrows, M. D.; Ryan, S. R.; Lamb, W. E. The Journal of Chemical Physics, Vol. 71, Issue 12 https://doi.org/10.1063/1.438306	journal	January 1979
Time‐dependent approach to semiclassical dynamics Heller, Eric J. The Journal of Chemical Physics, Vol. 62, Issue 4 https://doi.org/10.1063/1.430620	journal	February 1975
Intramolecular Hydrogen Migration in Alkylperoxy and Hydroperoxyalkylperoxy Radicals: Accurate Treatment of Hindered Rotors Sharma, Sandeep; Raman, Sumathy; Green, William H. The Journal of Physical Chemistry A, Vol. 114, Issue 18 https://doi.org/10.1021/jp9098792	journal	May 2010
Trajectory-Based Nonadiabatic Dynamics with Time-Dependent Density Functional Theory Curchod, Basile F. E.; Rothlisberger, Ursula; Tavernelli, Ivano ChemPhysChem, Vol. 14, Issue 7 https://doi.org/10.1002/cphc.201200941	journal	April 2013
Sequential and concerted C–C and C–O bond dissociation in the Coulomb explosion of 2-propanol Bittner, Dror M.; Gope, Krishnendu; Livshits, Ester The Journal of Chemical Physics, Vol. 157, Issue 7 https://doi.org/10.1063/5.0098531	journal	August 2022
Substituent effects on H ₃ ⁺ formation via H ₂ roaming mechanisms from organic molecules under strong-field photodissociation Ekanayake, Nagitha; Nairat, Muath; Weingartz, Nicholas P. The Journal of Chemical Physics, Vol. 149, Issue 24 https://doi.org/10.1063/1.5065387	journal	December 2018
A possible glycine radical in anaerobic ribonucleotide reductase from Escherichia coli: nucleotide sequence of the cloned nrdD gene. Sun, X.; Harder, J.; Krook, M. Proceedings of the National Academy of Sciences, Vol. 90, Issue 2 https://doi.org/10.1073/pnas.90.2.577	journal	January 1993
Coherent vibrations in methanol cation probed by periodic H3+ ejection after double ionization Ando, Toshiaki; Shimamoto, Akihiro; Miura, Shun Communications Chemistry, Vol. 1, Issue 1 https://doi.org/10.1038/s42004-017-0006-7	journal	March 2018
Cold Target Recoil Ion Momentum Spectroscopy: a ‘momentum microscope’ to view atomic collision dynamics Dörner, R.; Mergel, V.; Jagutzki, O. Physics Reports, Vol. 330, Issue 2-3 https://doi.org/10.1016/S0370-1573(99)00109-X	journal	June 2000
Post-translational activation introduces a free radical into pyruvate formate-lyase. Knappe, J.; Neugebauer, F. A.; Blaschkowski, H. P. Proceedings of the National Academy of Sciences, Vol. 81, Issue 5 https://doi.org/10.1073/pnas.81.5.1332	journal	March 1984
Imaging intramolecular hydrogen migration with time- and momentum-resolved photoelectron diffraction Ota, Fukiko; Abe, Shigeru; Hatada, Keisuke Physical Chemistry Chemical Physics, Vol. 23, Issue 36 https://doi.org/10.1039/D1CP02055B	journal	January 2021
Encoding of vinylidene isomerization in its anion photoelectron spectrum DeVine, Jessalyn A.; Weichman, Marissa L.; Laws, Benjamin Science, Vol. 358, Issue 6361 https://doi.org/10.1126/science.aao1905	journal	October 2017
Time-resolving the ultrafast H2 roaming chemistry and H3+ formation using extreme-ultraviolet pulses Livshits, Ester; Luzon, Itamar; Gope, Krishnendu Communications Chemistry, Vol. 3, Issue 1 https://doi.org/10.1038/s42004-020-0294-1	journal	April 2020
Determination of active sites for H atom rearrangement in dissociative ionization of ethanol Sharma, Vandana; Bapat, B. The Journal of Chemical Physics, Vol. 125, Issue 4 https://doi.org/10.1063/1.2234773	journal	July 2006
Ultrafast hydrogen migration in allene in intense laser fields: Evidence of two-body Coulomb explosion Xu, Huailiang; Okino, Tomoya; Yamanouchi, Kaoru Chemical Physics Letters, Vol. 469, Issue 4-6 https://doi.org/10.1016/j.cplett.2008.12.097	journal	February 2009
Hydrogen migration as a potential driving force in the thermal decomposition of dimethoxymethane: New insights from pyrolysis imaging photoelectron photoion coincidence spectroscopy and computations Yu, Tongpo; Wu, Xiangkun; Zhou, Xiaoguo Combustion and Flame, Vol. 222 https://doi.org/10.1016/j.combustflame.2020.08.040	journal	December 2020
Capturing roaming molecular fragments in real time Endo, Tomoyuki; Neville, Simon P.; Wanie, Vincent Science, Vol. 370, Issue 6520 https://doi.org/10.1126/science.abc2960	journal	November 2020
Wave packet bifurcation in ultrafast hydrogen migration in CH3OH+ by pump-probe coincidence momentum imaging with few-cycle laser pulses Ando, Toshiaki; Shimamoto, Akihiro; Miura, Shun Chemical Physics Letters, Vol. 624 https://doi.org/10.1016/j.cplett.2015.02.017	journal	March 2015
Communication: Long-lived neutral H ₂ in hydrogen migration within methanol dication Nakai, K.; Kato, T.; Kono, H. The Journal of Chemical Physics, Vol. 139, Issue 18 https://doi.org/10.1063/1.4830397	journal	November 2013
Time-resolved molecular dynamics of single and double hydrogen migration in ethanol Kling, Nora G.; Díaz-Tendero, S.; Obaid, R. Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10571-9	journal	June 2019
Efficient ejection of H3+ from hydrocarbon molecules induced by ultrashort intense laser fields Hoshina, Kennosuke; Furukawa, Yusuke; Okino, Tomoya The Journal of Chemical Physics, Vol. 129, Issue 10 https://doi.org/10.1063/1.2973588	journal	September 2008
Hydrogen scrambling in ethane induced by intense laser fields: Statistical analysis of coincidence events Kanya, Reika; Kudou, Tatsuya; Schirmel, Nora The Journal of Chemical Physics, Vol. 136, Issue 20 https://doi.org/10.1063/1.4720503	journal	May 2012
Single-shot carrier-envelope-phase tagging using an f –2 f interferometer and a phase meter: a comparison Ren, Xiaoming; Summers, A. M.; Raju P., Kanaka Journal of Optics, Vol. 19, Issue 12 https://doi.org/10.1088/2040-8986/aa9865	journal	November 2017
Intramolecular Hydrogen Shift Chemistry of Hydroperoxy-Substituted Peroxy Radicals Praske, Eric; Otkjær, Rasmus V.; Crounse, John D. The Journal of Physical Chemistry A, Vol. 123, Issue 2 https://doi.org/10.1021/acs.jpca.8b09745	journal	December 2018
Coincidence momentum imaging of ejection of hydrogen molecular ions from methanol in intense laser fields Okino, Tomoya; Furukawa, Yusuke; Liu, Peng Chemical Physics Letters, Vol. 419, Issue 1-3 https://doi.org/10.1016/j.cplett.2005.11.059	journal	February 2006
Advances in Hydrogen/Deuterium Exchange Mass Spectrometry and the Pursuit of Challenging Biological Systems James, Ellie I.; Murphree, Taylor A.; Vorauer, Clint Chemical Reviews, Vol. 122, Issue 8 https://doi.org/10.1021/acs.chemrev.1c00279	journal	September 2021
Atomic structure dependence of nonsequential double ionization of He, Ne and Ar in strong laser pulses Jesus, V. L. B. de; Feuerstein, B.; Zrost, K. Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 37, Issue 8 https://doi.org/10.1088/0953-4075/37/8/L03	journal	April 2004
Two-body dissociation of formic acid following double ionization by ultrafast laser pulses Severt, T.; Daugaard, Darwin R.; Townsend, Tiana Physical Review A, Vol. 105, Issue 5 https://doi.org/10.1103/PhysRevA.105.053112	journal	May 2022
Bond rearrangement during Coulomb explosion of water molecules Leonard, M.; Sayler, A. M.; Carnes, K. D. Physical Review A, Vol. 99, Issue 1 https://doi.org/10.1103/PhysRevA.99.012704	journal	January 2019
Fragmentation dynamics of the methanol dication Kushawaha, R. K.; Bapat, B. Chemical Physics Letters, Vol. 463, Issue 1-3 https://doi.org/10.1016/j.cplett.2008.08.019	journal	September 2008
Recoil-ion and electron momentum spectroscopy: reaction-microscopes Ullrich, J.; Moshammer, R.; Dorn, A. Reports on Progress in Physics, Vol. 66, Issue 9 https://doi.org/10.1088/0034-4885/66/9/203	journal	August 2003
Ultrafast molecular dynamics in ionized 1- and 2-propanol: from simple fragmentation to complex isomerization and roaming mechanisms Mishra, Debadarshini; Reino-González, Juan; Obaid, Razib Physical Chemistry Chemical Physics, Vol. 24, Issue 1 https://doi.org/10.1039/D1CP04011A	journal	January 2022
Hydrogen Atom Scrambling in Ion‐Molecule Reactions of Methane and Ethylene Huntress, Wesley T. The Journal of Chemical Physics, Vol. 56, Issue 10 https://doi.org/10.1063/1.1676996	journal	May 1972
Mechanisms and time-resolved dynamics for trihydrogen cation (H3 +) formation from organic molecules in strong laser fields Ekanayake, Nagitha; Nairat, Muath; Kaderiya, Balram Scientific Reports, Vol. 7, Issue 1 https://doi.org/10.1038/s41598-017-04666-w	journal	July 2017
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
Roaming-mediated ultrafast isomerization of geminal tri-bromides in the gas and liquid phases Mereshchenko, Andrey S.; Butaeva, Evgeniia V.; Borin, Veniamin A. Nature Chemistry, Vol. 7, Issue 7 https://doi.org/10.1038/nchem.2278	journal	June 2015
Unusual mechanism for H ₃ ⁺ formation from ethane as obtained by femtosecond laser pulse ionization and quantum chemical calculations Kraus, Peter M.; Schwarzer, Martin C.; Schirmel, Nora The Journal of Chemical Physics, Vol. 134, Issue 11 https://doi.org/10.1063/1.3561311	journal	March 2011
No Straight Path: Roaming in Both Ground- and Excited-State Photolytic Channels of NO3 -> NO + O2 Grubb, M. P.; Warter, M. L.; Xiao, H. Science, Vol. 335, Issue 6072 https://doi.org/10.1126/science.1216911	journal	March 2012
Rapid formation of H ⁺ ₃ from ammonia and methane following 4 MeV proton impact Jochim, Bethany; Lueking, Amy; Doshier, Laura Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 42, Issue 9 https://doi.org/10.1088/0953-4075/42/9/091002	journal	April 2009
H2 roaming chemistry and the formation of H3+ from organic molecules in strong laser fields Ekanayake, Nagitha; Severt, Travis; Nairat, Muath Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-07577-0	journal	December 2018

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Title: Initial-site characterization of hydrogen migration following strong-field double-ionization of ethanol

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