Absolute Photoionization Cross Section of the Simplest Enol, Vinyl Alcohol

Rösch, Daniel; Caravan, Rebecca L.; Taatjes, Craig A.; Au, Kendrew; Almeida, Raybel; Osborn, David L.

doi:10.1021/acs.jpca.1c05825

Absolute Photoionization Cross Section of the Simplest Enol, Vinyl Alcohol

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

DOI:https://doi.org/10.1021/acs.jpca.1c05825· OSTI ID:1840724

^[1]; ^[2]; ^[1]; Au, Kendrew ^[1]; Almeida, Raybel ^[1]; ^[3]

Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Argonne National Lab. (ANL), Lemont, IL (United States)
Sandia National Lab. (SNL-CA), Livermore, CA (United States); Univ. of California, Davis, CA (United States)

The absolute photoionization cross section of vinyl alcohol was determined by multiplexed photoionization mass spectrometry of the Norrish type II photodissociation of butanal at 308 nm. The measured cross sections at 10.005 and 10.205 eV are 7.5 ± 1.9 MB and 8.1 ± 1.9 MB respectively. Here, a higher signal-to-noise ratio photoionization spectrum of vinyl alcohol was recorded via the pyrolysis of 2-chloroethanol and scaled to the absolute cross sections measured using the Norrish type II method. From comparison of our spectrum with previously reported photoelectron spectra we conclude that vinyl alcohol is mainly ionized by direct ionization in the energy range 9 – 9.6 eV, whereas autoionization is responsible for the steady rise in the photoionization spectrum above the end of the Franck-Condon envelope at 9.9 eV.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

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

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1840724

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: 36 Vol. 125; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (43)

Carboxylic Acid Catalyzed Keto-Enol Tautomerizations in the Gas Phase da Silva, Gabriel Angewandte Chemie International Edition, Vol. 49, Issue 41 https://doi.org/10.1002/anie.201003530	journal	September 2010
Ueber Phenylbrommilchsäure Erlenmeyer, Emil Berichte der deutschen chemischen Gesellschaft, Vol. 13, Issue 1 https://doi.org/10.1002/cber.18800130187	journal	January 1880
Chemically Induced Dynamic Nuclear Polarization XI. Intermediary vinyl alcohol during photochemical reactions of acetaldehyde and of acetoin Blank, B.; Fischer, H. Helvetica Chimica Acta, Vol. 56, Issue 1 https://doi.org/10.1002/hlca.19730560147	journal	January 1973
Molecular Ions of Transient Species: Vinyl-Alcohol Cation Albrecht, Bruno; Allan, Michael; Haselbach, Edwin Helvetica Chimica Acta, Vol. 67, Issue 1 https://doi.org/10.1002/hlca.19840670127	journal	February 1984
The kinetics and mechanism of n -butyraldehyde photolysis in the vapor phase at 313 nm: PHOTOLYSIS OF n -BUTYRALDEHYDE Förgeteg, S.; Bérces, T.; Dóbé, S. International Journal of Chemical Kinetics, Vol. 11, Issue 3 https://doi.org/10.1002/kin.550110302	journal	March 1979
Formation of interstellar vinyl alcohol via simple radical processes: Theoretical study: Interstellar Vinyl Alcohol Basiuk, Vladimir A.; Kobayashi, Kensei International Journal of Quantum Chemistry, Vol. 97, Issue 2 https://doi.org/10.1002/qua.10710	journal	October 2003
High-Resolution Fourier Transform Infrared Spectroscopy of Vinyl Alcohol: Rotational Analysis of the ν13 CH2 Wagging Fundamental at 817 cm−1 Joo, Duck-Lae; Merer, A. J.; Clouthier, Dennis J. Journal of Molecular Spectroscopy, Vol. 197, Issue 1 https://doi.org/10.1006/jmsp.1999.7877	journal	September 1999
Theoretical study of reaction mechanisms for the ketonization of vinyl alcohol in gas phase and aqueous solution Ventura, Oscar N.; Lled�s, Agust�; Bonaccorsi, Rosanna Theoretica Chimica Acta, Vol. 72, Issue 3 https://doi.org/10.1007/BF00527661	journal	October 1987
�ber Absorptionsserien von Argon, Krypton und Xenon zu Termen zwischen den beiden Ionisierungsgrenzen2 P 3 2/0 und2 P 1 2/0 Beutler, H. Zeitschrift f�r Physik, Vol. 93, Issue 3-4 https://doi.org/10.1007/BF01365116	journal	March 1935
Microwave spectroscopic detection of vinyl alcohol, CH2CHOH Saito, Shuji Chemical Physics Letters, Vol. 42, Issue 3 https://doi.org/10.1016/0009-2614(76)80638-0	journal	September 1976
Microwave spectrum, dipole moment, and structure of anti-vinyl alcohol Rodler, M. Journal of Molecular Spectroscopy, Vol. 114, Issue 1 https://doi.org/10.1016/0022-2852(85)90332-7	journal	November 1985
A photoionization and molecular orbital study of cyclobutanol and cyclobutylamine radical cations Bouchoux, Guy; Alcaraz, Christian; Dutuit, Odile International Journal of Mass Spectrometry and Ion Processes, Vol. 137 https://doi.org/10.1016/0168-1176(94)04049-4	journal	October 1994
Photoelectron spectroscopic detection of vinyl alcohol, CH2CHOH: evidence for the syn and anti rotamers Matti, George Y.; Osman, Osman I.; Upham, John E. Journal of Electron Spectroscopy and Related Phenomena, Vol. 49, Issue 2 https://doi.org/10.1016/0368-2048(89)85008-X	journal	January 1989
Pressure dependence of the photooxidation of selected carbonyl compounds in air: n -butanal and n -pentanal Tadić, Jovan; Juranić, Ivan; Moortgat, Geert K. Journal of Photochemistry and Photobiology A: Chemistry, Vol. 143, Issue 2-3 https://doi.org/10.1016/S1010-6030(01)00524-X	journal	October 2001
Photoionization cross sections for reaction intermediates in hydrocarbon combustion Cool, Terrill A.; Wang, Juan; Nakajima, Koichi International Journal of Mass Spectrometry, Vol. 247, Issue 1-3 https://doi.org/10.1016/j.ijms.2005.08.018	journal	December 2005
Infrared Spectra of Gas-Phase 1- and 2-Propenol Isomers Shaw, Miranda F.; Osborn, David L.; Jordan, Meredith J. T. The Journal of Physical Chemistry A, Vol. 121, Issue 19 https://doi.org/10.1021/acs.jpca.7b02323	journal	May 2017
Atmospheric Chemistry of Enols: Vinyl Alcohol + OH + O ₂ Reaction Revisited Lei, Xiaoyang; Wang, Weina; Cai, Jie The Journal of Physical Chemistry A, Vol. 123, Issue 14 https://doi.org/10.1021/acs.jpca.8b12240	journal	March 2019
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
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds Stull, Daniel R. Industrial & Engineering Chemistry, Vol. 39, Issue 4 https://doi.org/10.1021/ie50448a022	journal	April 1947
Structure of syn-vinyl alcohol determined by microwave spectroscopy Rodler, Martin; Bauder, A. Journal of the American Chemical Society, Vol. 106, Issue 14 https://doi.org/10.1021/ja00326a024	journal	July 1984
Infrared spectrum and general valence force field of syn-vinyl alcohol Rodler, Martin; Blom, C. E.; Bauder, A. Journal of the American Chemical Society, Vol. 106, Issue 14 https://doi.org/10.1021/ja00326a025	journal	July 1984
Heats of formation of ionic and neutral enols of acetaldehyde and acetone Holmes, J. L.; Lossing, F. P. Journal of the American Chemical Society, Vol. 104, Issue 9 https://doi.org/10.1021/ja00373a058	journal	May 1982
An ab initio molecular orbital study of the structures and stabilities of the C2H4O+.cntdot. isomers Bouma, Willem J.; MacLeod, John K.; Radom, Leo Journal of the American Chemical Society, Vol. 101, Issue 19 https://doi.org/10.1021/ja00513a015	journal	September 1979
The Photolysis of the Alphatic Aldehydes. XIV. The Butyraldehydes ¹ Blacet, F. E.; Calvert, J. G. Journal of the American Chemical Society, Vol. 73, Issue 2 https://doi.org/10.1021/ja01146a048	journal	February 1951
Combustion Chemistry of Enols: Possible Ethenol Precursors in Flames ^† Taatjes, Craig A.; Hansen, Nils; Miller, James A. The Journal of Physical Chemistry A, Vol. 110, Issue 9 https://doi.org/10.1021/jp0547313	journal	March 2006
Photochemistry and Photophysics of n -Butanal, 3-Methylbutanal, and 3,3-Dimethylbutanal: Experimental and Theoretical Study Tadić, Jovan M.; Moortgat, Geert K.; Bera, Partha P. The Journal of Physical Chemistry A, Vol. 116, Issue 24 https://doi.org/10.1021/jp208665v	journal	November 2011
Low-Temperature Combustion Chemistry of n- Butanol: Principal Oxidation Pathways of Hydroxybutyl Radicals Welz, Oliver; Zádor, Judit; Savee, John D. The Journal of Physical Chemistry A, Vol. 117, Issue 46 https://doi.org/10.1021/jp403792t	journal	May 2013
Reaction of the C ₂ H Radical with 1-Butyne (C ₄ H ₆ ): Low-Temperature Kinetics and Isomer-Specific Product Detection ^† Soorkia, Satchin; Trevitt, Adam J.; Selby, Talitha M. The Journal of Physical Chemistry A, Vol. 114, Issue 9 https://doi.org/10.1021/jp911132r	journal	March 2010
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
Atmospheric transformation of enols: A potential secondary source of carboxylic acids in the urban troposphere Archibald, Alex T.; McGillen, Max R.; Taatjes, Craig A. Geophysical Research Letters, Vol. 34, Issue 21 https://doi.org/10.1029/2007GL031032	journal	January 2007
New mechanistic insights to the O(3P) + propene reaction from multiplexed photoionization mass spectrometry Savee, John D.; Welz, Oliver; Taatjes, Craig A. Physical Chemistry Chemical Physics, Vol. 14, Issue 30 https://doi.org/10.1039/c2cp41200d	journal	January 2012
Selective detection of isomers with photoionization mass spectrometry for studies of hydrocarbon flame chemistry Cool, Terrill A.; Nakajima, Koichi; Mostefaoui, Toufik A. The Journal of Chemical Physics, Vol. 119, Issue 16 https://doi.org/10.1063/1.1611173	journal	October 2003
The multiplexed chemical kinetic photoionization mass spectrometer: A new approach to isomer-resolved chemical kinetics Osborn, David L.; Zou, Peng; Johnsen, Howard Review of Scientific Instruments, Vol. 79, Issue 10 https://doi.org/10.1063/1.3000004	journal	October 2008
Absolute photoionization cross-section of the propargyl radical Savee, John D.; Soorkia, Satchin; Welz, Oliver The Journal of Chemical Physics, Vol. 136, Issue 13 https://doi.org/10.1063/1.3698282	journal	April 2012
Predominant decay channel for superexcited organic molecules Koizumi, Hitoshi The Journal of Chemical Physics, Vol. 95, Issue 8 https://doi.org/10.1063/1.461605	journal	October 1991
The heats of formation of some C ₂ H ₅ O ⁺ isomers, relevant bond energies in ethanol and PA(CH ₃ CHO) Ruscic, B.; Berkowitz, J. The Journal of Chemical Physics, Vol. 101, Issue 12 https://doi.org/10.1063/1.467843	journal	December 1994
A complete basis set model chemistry. VI. Use of density functional geometries and frequencies Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W. The Journal of Chemical Physics, Vol. 110, Issue 6 https://doi.org/10.1063/1.477924	journal	February 1999
Microwave Detection of Interstellar Vinyl Alcohol, CH[TINF]2[/TINF][dbond]CHOH Turner, B. E.; Apponi, A. J. The Astrophysical Journal, Vol. 561, Issue 2 https://doi.org/10.1086/324762	journal	November 2001
Solid-Phase Formation of Interstellar Vinyl Alcohol Hudson, R. L.; Moore, M. H. The Astrophysical Journal, Vol. 586, Issue 1 https://doi.org/10.1086/374580	journal	March 2003
Laboratory Studies on the Formation of Three C ₂ H ₄ O Isomers—Acetaldehyde (CH ₃ CHO), Ethylene Oxide (c‐C ₂ H ₄ O), and Vinyl Alcohol (CH ₂ CHOH)—in Interstellar and Cometary Ices Bennett, Chris J.; Osamura, Yoshihiro; Lebar, Matt D. The Astrophysical Journal, Vol. 634, Issue 1 https://doi.org/10.1086/452618	journal	November 2005
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
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
Far-infrared Spectroscopic Characterization of Anti -vinyl Alcohol Bunn, Hayley; Soliday, Rebekah M.; Sumner, Isaiah The Astrophysical Journal, Vol. 847, Issue 1 https://doi.org/10.3847/1538-4357/aa8870	journal	September 2017

Similar Records

Note: Absolute photoionization cross-section of the vinyl radical

Journal Article · Wed Aug 07 00:00:00 EDT 2013 · Journal of Chemical Physics · OSTI ID:1082640

Photoionization study of the vinyl radical

Journal Article · Wed Jun 15 00:00:00 EDT 1988 · J. Chem. Phys.; (United States) · OSTI ID:5183071

Photoionization and electron-impact ionization of Ar{sup 5+}

Journal Article · Fri Jun 15 00:00:00 EDT 2007 · Physical Review. A · OSTI ID:20991147

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Energy
Ionization
Photodissociation
Photoionization
Pyrolysis

Absolute Photoionization Cross Section of the Simplest Enol, Vinyl Alcohol

Citation Formats

References (43)

Similar Records

Related Subjects