Dynamics of hydride anion and acetyloxyl radical production by electron attachment to acetic acid

Hasan, M.; Weber, Th; Centurion, M.; Slaughter, D. S.

doi:10.1063/5.0226252

Title: Dynamics of hydride anion and acetyloxyl radical production by electron attachment to acetic acid

Journal Article · 22 October 2024 · Journal of Chemical Physics

DOI: https://doi.org/10.1063/5.0226252 · OSTI ID:2473057

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Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Univ. of Nebraska, Lincoln, NE (United States)
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Univ. of Nebraska, Lincoln, NE (United States)

Here, we investigate the dynamics and site-selectivity in the dissociation of transient anions formed upon attachment of low energy electrons to acetic acid by anion fragment momentum imaging experiments. The resonances at 6.7 and 7.7 eV are confirmed to dissociate exclusively by the O–H bond, while a third resonance at 9.1 eV dissociates primarily by both C–H break and O–H break. A fourth resonance near 10 eV is found to dissociate by O–H break. For each resonance, the measured kinetic energy release indicates two-body dissociation produces a neutral radical in the ground electronic state, for all four resonances. The measured angular distributions are consistent with all four resonances having A' symmetry.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: AC02-05CH11231; SC0019482

OSTI ID:: 2473057

Journal Information:: Journal of Chemical Physics, Journal Name: Journal of Chemical Physics Journal Issue: 16 Vol. 161; ISSN 0021-9606

Publisher:: American Institute of Physics (AIP)Copyright Statement

Country of Publication:: United States

Language:: English

References (52)

Vacuum ultraviolet absorption spectra and electronic structures of formic acid, acetic acid and ethyl acetate Nagakura, S.; Kaya, K.; Tsubomura, H. Journal of Molecular Spectroscopy, Vol. 13, Issue 1-4 https://doi.org/10.1016/0022-2852(64)90049-9	journal	January 1964
Microwave spectra and centrifugal distortion constants of formic acid containing 13C and 18O: Refinement of the harmonic force field and the molecular structure Davis, R. Wellington; Robiette, A. G.; Gerry, M. C. L. Journal of Molecular Spectroscopy, Vol. 81, Issue 1 https://doi.org/10.1016/0022-2852(80)90331-8	journal	May 1980
A reinvestigation of the molecular structure of acetic acid monomer and dimer by gas electron diffraction Derissen, J. L. Journal of Molecular Structure, Vol. 7, Issue 1-2 https://doi.org/10.1016/0022-2860(71)90008-1	journal	January 1971
Dissociative electron attachment to acetic acid (CH3COOH) Sailer, Wolfgang; Pelc, Andrzej; Probst, Michael Chemical Physics Letters, Vol. 378, Issue 3-4 https://doi.org/10.1016/S0009-2614(03)01285-5	journal	September 2003
Electron attachment to simple organic acids Pelc, A.; Sailer, W.; Scheier, P. Vacuum, Vol. 70, Issue 2-3 https://doi.org/10.1016/S0042-207X(02)00682-6	journal	March 2003
Valence–shell electron energy-loss spectra of formic acid and acetic acid Ari, Tayfun; Haluk Güven, M. Journal of Electron Spectroscopy and Related Phenomena, Vol. 106, Issue 1 https://doi.org/10.1016/S0368-2048(99)00084-5	journal	January 2000
VUV absorption spectrum of acetic acid between 6 and 20eV Leach, Sydney; Schwell, Martin; Un, Sun Chemical Physics, Vol. 321, Issue 1-2 https://doi.org/10.1016/j.chemphys.2005.08.044	journal	January 2006
Acetic acid electronic state spectroscopy by high-resolution vacuum ultraviolet photo-absorption, electron impact, He(I) photoelectron spectroscopy and ab initio calculations Limão-Vieira, P.; Giuliani, A.; Delwiche, J. Chemical Physics, Vol. 324, Issue 2-3 https://doi.org/10.1016/j.chemphys.2005.10.032	journal	May 2006
Electron stimulated desorption of H− ions from condensed acetic acid Bertin, M.; Cáceres, D.; Davis, M. P. Chemical Physics Letters, Vol. 433, Issue 4-6 https://doi.org/10.1016/j.cplett.2006.11.052	journal	January 2007
Generation of (M–H)− ions by dissociative electron attachment to simple organic acids M Pelc, A.; Sailer, W.; Scheier, P. Vacuum, Vol. 78, Issue 2-4 https://doi.org/10.1016/j.vacuum.2005.01.099	journal	May 2005
Hydrogen Abstraction of Acetic Acid by Hydrogen Atom to Form Carboxymethyl Radical •CH₂C(O)OH in Solid para-Hydrogen and Its Implication in Astrochemistry Joshi, Prasad Ramesh; How, Kylie Chia-Yee; Lee, Yuan-Pern ACS Earth and Space Chemistry, Vol. 5, Issue 1 https://doi.org/10.1021/acsearthspacechem.0c00316	journal	January 2021
Fluorescence yields from photodissociative excitation of formic acid, methyl formate, and acetic acid in the vacuum-ultraviolet region Suto, Masako; Wang, Xiuyan; Lee, L. C. The Journal of Physical Chemistry, Vol. 92, Issue 13 https://doi.org/10.1021/j100324a015	journal	June 1988
Pulse radiolysis of aliphatic acids in aqueous solutions. I. Simple monocarboxylic acids Neta, Pedatsur; Simic, Miomir; Hayon, Elie The Journal of Physical Chemistry, Vol. 73, Issue 12 https://doi.org/10.1021/j100846a029	journal	December 1969
Heats of formation of oxygen-containing organic free radicals from appearance energy measurements Holmes, John L.; Lossing, Fred P.; Mayer, Paul M. Journal of the American Chemical Society, Vol. 113, Issue 26 https://doi.org/10.1021/ja00026a002	journal	December 1991
Carboxyl Free Radicals: Formyloxyl (HCOO.bul.) and Acetyloxyl (CH3COO.bul.) Revisited Rauk, Arvi; Yu, Dake; Armstrong, David A. Journal of the American Chemical Society, Vol. 116, Issue 18 https://doi.org/10.1021/ja00097a031	journal	September 1994
Gas-Phase Properties and Reactivity of the Acetate Radical Anion. Determination of the C-H Bond Strengths in Acetic Acid and Acetate Ion Wenthold, Paul G.; Squires, Robert R. Journal of the American Chemical Society, Vol. 116, Issue 26 https://doi.org/10.1021/ja00105a032	journal	December 1994
Intrinsic acidities of carboxylic acids from gas-phase acid equilibriums Yamdagni, R.; Kebarle, P. Journal of the American Chemical Society, Vol. 95, Issue 12 https://doi.org/10.1021/ja00793a038	journal	June 1973
Dynamics of the Acetyloxyl Radical Studied by Dissociative Photodetachment of the Acetate Anion ^† Lu, Zhou; Continetti, Robert E. The Journal of Physical Chemistry A, Vol. 108, Issue 45 https://doi.org/10.1021/jp040355v	journal	November 2004
Determination of the Electron Affinity of the Acetyloxyl Radical (CH ₃ COO) by Low-Temperature Anion Photoelectron Spectroscopy and ab Initio Calculations Wang, Xue-Bin; Woo, Hin-Koon; Wang, Lai-Sheng The Journal of Physical Chemistry A, Vol. 110, Issue 15 https://doi.org/10.1021/jp060138p	journal	April 2006
Ab Initio/Density Functional Theory and Multichannel RRKM Calculations for the CH ₃ O + CO Reaction Wang, Baoshan; Hou, Hua; Gu, Yueshu The Journal of Physical Chemistry A, Vol. 103, Issue 40 https://doi.org/10.1021/jp991203g	journal	September 1999
Dissociative electron attachment to H2S probed by ion momentum imaging Ram, N. Bhargava; Krishnakumar, E. Physical Chemistry Chemical Physics, Vol. 13, Issue 30 https://doi.org/10.1039/C1CP20642G	journal	January 2011
DEA dynamics of chlorine dioxide probed by velocity slice imaging Gope, Krishnendu; Mason, Nigel; Krishnakumar, E. Physical Chemistry Chemical Physics, Vol. 21, Issue 26 https://doi.org/10.1039/C8CP06660D	journal	January 2019
Dissociation dynamics in low energy electron attachment to ammonia using velocity slice imaging Chakraborty, Dipayan; Giri, Aranya; Nandi, Dhananjay Physical Chemistry Chemical Physics, Vol. 21, Issue 39 https://doi.org/10.1039/C9CP03973B	journal	January 2019
Selective bond-breaking in formic acid by dissociative electron attachment Slaughter, D. S.; Weber, Th.; Belkacem, A. Physical Chemistry Chemical Physics, Vol. 22, Issue 25 https://doi.org/10.1039/D0CP01522A	journal	January 2020
Oxidation of carbon monoxide by methoxy-radicals Lissi, E. A.; Massiff, G.; Villa, A. E. Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, Vol. 69, Issue 0 https://doi.org/10.1039/F19736900346	journal	January 1973
Vacuum ultra-violet spectra of formic and acetic acids Bell, Stephen; Ng, T. L.; Walsh, A. D. Journal of the Chemical Society, Faraday Transactions 2, Vol. 71 https://doi.org/10.1039/F29757100393	journal	January 1975
What Woodward and Hoffmann didn't tell us: the failure of the Born–Oppenheimer approximation in competing reaction pathways Waschewsky, Gabriela C. G.; Kash, Phillip W.; Myers, Tanya L. J. Chem. Soc., Faraday Trans., Vol. 90, Issue 12 https://doi.org/10.1039/FT9949001581	journal	January 1994
Gas phase fragmentation of protonated betaine and its clusters Wyer, Jean Ann; Feketeová, Linda; Brøndsted Nielsen, Steen Physical Chemistry Chemical Physics, Vol. 11, Issue 39 https://doi.org/10.1039/b909653a	journal	January 2009
Mechanism for ultrafast internal conversion of adenine Kang, Hyuk; Jung, Boyong; Kim, Seong Keun The Journal of Chemical Physics, Vol. 118, Issue 15 https://doi.org/10.1063/1.1566438	journal	April 2003
Dissociation of H ₂ ⁺ by Electron Impact: Calculated Angular Distribution Zare, Richard N. The Journal of Chemical Physics, Vol. 47, Issue 1 https://doi.org/10.1063/1.1711847	journal	July 1967
Correlations among Electronic Transitions for Carbonyl and for Carboxyl in the Vacuum Ultraviolet Barnes, Edwin E.; Simpson, William T. The Journal of Chemical Physics, Vol. 39, Issue 3 https://doi.org/10.1063/1.1734305	journal	August 1963
Functional group dependent dissociative electron attachment to simple organic molecules Prabhudesai, Vaibhav S.; Nandi, Dhananjay; Kelkar, Aditya H. The Journal of Chemical Physics, Vol. 128, Issue 15 https://doi.org/10.1063/1.2899330	journal	April 2008
A momentum imaging microscope for dissociative electron attachment Adaniya, H.; Slaughter, D. S.; Osipov, T. Review of Scientific Instruments, Vol. 83, Issue 2 https://doi.org/10.1063/1.3685244	journal	February 2012
Communication: Observation of dipole-bound state and high-resolution photoelectron imaging of cold acetate anions Huang, Dao-Ling; Zhu, Guo-Zhu; Wang, Lai-Sheng The Journal of Chemical Physics, Vol. 142, Issue 9 https://doi.org/10.1063/1.4913924	journal	March 2015
Differential cross sections and angular distributions of H^-from dissociative electron attachment to H₂between 3.75 eV and 13 eV Journal of Physics B: Atomic and Molecular Physics, Vol. 10, Issue 2 https://doi.org/10.1088/0022-3700/10/2/017	journal	February 1977
Dissociative electron attachment on H 2 S: energy and angular distributions of H - ions Azria, R.; Coat, Y. Le; Lefevre, G. Journal of Physics B: Atomic and Molecular Physics, Vol. 12, Issue 4 https://doi.org/10.1088/0022-3700/12/4/016	journal	February 1979
Fragmentation of transient water anions following low-energy electron capture by H ₂ O/D ₂ O Fedor, J.; Cicman, P.; Coupier, B. Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 39, Issue 18 https://doi.org/10.1088/0953-4075/39/18/022	journal	September 2006
Absolute cross sections for dissociative electron attachment to H₂O and D₂O Rawat, Prashant; Prabhudesai, Vaibhav S.; Aravind, G. Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 40, Issue 24 https://doi.org/10.1088/0953-4075/40/24/007	journal	November 2007
Dissociative electron attachment to carbon dioxide via the 8.2 eV Feshbach resonance Slaughter, D. S.; Adaniya, H.; Rescigno, T. N. Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 44, Issue 20 https://doi.org/10.1088/0953-4075/44/20/205203	journal	September 2011
Ion-momentum imaging of dissociative attachment of electrons to molecules Slaughter, D. S.; Belkacem, A.; McCurdy, C. W. Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 49, Issue 22 https://doi.org/10.1088/0953-4075/49/22/222001	journal	October 2016
Dissociative electron attachment studies of gas-phase acetic acid using a velocity map imaging technique Chakraborty, Dipayan; Kharchilava, Giorgi; Carmichael, Ian Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 56, Issue 24 https://doi.org/10.1088/1361-6455/ad1745	journal	December 2023
Probing site selective fragmentation of molecules containing hydroxyl group using Velocity Slice Imaging Prabhudesai, Vaibhav S.; Ram, N. Bhargava; Aravind, G. Journal of Physics: Conference Series, Vol. 80 https://doi.org/10.1088/1742-6596/80/1/012016	journal	September 2007
Kinetic-Energy Distribution of Negative Ions Formed by Dissociative Attachment and the Measurement of the Electron Affinity of Oxygen Chantry, P. J.; Schulz, G. J. Physical Review, Vol. 156, Issue 1 https://doi.org/10.1103/PhysRev.156.134	journal	April 1967
Angular Dependence of Scattering Products in Electron-Molecule Resonant Excitation and in Dissociative Attachment O'Malley, Thomas F.; Taylor, Howard S. Physical Review, Vol. 176, Issue 1 https://doi.org/10.1103/PhysRev.176.207	journal	December 1968
Effects of π−σ coupling on dissociative-electron-attachment angular distributions in vinyl, allyl, and benzyl chloride and in chlorobenzene Nag, Pamir; Tarana, Michal; Fedor, Juraj Physical Review A, Vol. 103, Issue 3 https://doi.org/10.1103/PhysRevA.103.032830	journal	March 2021
Dynamics of resonant low-energy electron attachment to ethanol-producing hydroxide anions Chakraborty, Dipayan; Slaughter, Daniel S.; Ptasinska, Sylwia Physical Review A, Vol. 108, Issue 5 https://doi.org/10.1103/PhysRevA.108.052806	journal	November 2023
Angular Distribution of O − from Dissociative Electron Attachment to O 2 Van Brunt, R. J.; Kieffer, L. J. Physical Review A, Vol. 2, Issue 5 https://doi.org/10.1103/PhysRevA.2.1899	journal	November 1970
Angular dependence of dissociative electron attachment to polyatomic molecules: Application to the B 1 2 metastable state of the H 2 O and H 2 S anions Haxton, Daniel J.; McCurdy, C. William; Rescigno, Thomas N. Physical Review A, Vol. 73, Issue 6 https://doi.org/10.1103/PhysRevA.73.062724	journal	June 2006
Low-energy electron collisions with acetic acid Freitas, T. C.; Varella, M. T. do N.; da Costa, R. F. Physical Review A, Vol. 79, Issue 2 https://doi.org/10.1103/PhysRevA.79.022706	journal	February 2009
Observation of the dynamics leading to a conical intersection in dissociative electron attachment to water Haxton, D. J.; Adaniya, H.; Slaughter, D. S. Physical Review A, Vol. 84, Issue 3 https://doi.org/10.1103/PhysRevA.84.030701	journal	September 2011
Functional Group Dependent Site Specific Fragmentation of Molecules by Low Energy Electrons Prabhudesai, Vaibhav S.; Kelkar, Aditya H.; Nandi, Dhananjay Physical Review Letters, Vol. 95, Issue 14 https://doi.org/10.1103/PhysRevLett.95.143202	journal	September 2005
Resonances in Electron Impact on Diatomic Molecules Schulz, George J. Reviews of Modern Physics, Vol. 45, Issue 3 https://doi.org/10.1103/RevModPhys.45.423	journal	July 1973

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Title: Dynamics of hydride anion and acetyloxyl radical production by electron attachment to acetic acid

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