Spectroscopy of Ethylenedione and Ethynediolide: A Reinvestigation

Katharine G. Lunny; Yanice Benitez; Yishai Albeck; Daniel Strasser; John F. Stanton; Robert E. Continetti

doi:10.1002/anie.201801848

Spectroscopy of Ethylenedione and Ethynediolide: A Reinvestigation

Katharine G. Lunny, Yanice Benitez, Yishai Albeck, Daniel Strasser, John F. Stanton, Robert E. Continetti^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

In an effort to characterize the electronic states of ethylenedione, OCCO, photoelectron-photofragment coincidence (PPC) spectroscopy was applied to measure anions at m/z 56 and 57 using a pulsed discharge of glyoxal vapor and N₂O. PPC measurements at a photon energy of 3.20 eV yield photoelectron spectra in coincidence with either neutral photofragments or stable neutral products. The measurements showed that primarily stable neutral products were formed, with photoelectron spectra consistent with the oxyallyl diradical, C₃H₄O, and acetone enolate radical, C₃H₅O. The spectra were also found to have features nearly identical to those reported for OCCO and HOCCO by Sanov and co-workers. The stability of the neutral products, as well as an examination of spectra reported for the oxyallyl anion and acetone enolate show that the previous assignments of OCCO and HOCCO are in error, and are instead attributed here to the oxyallyl diradical, C₃H₄O, and the acetone enolate radical, C₃H₅O.

Original language	American English
Pages (from-to)	5394-5397
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	19
DOIs	https://doi.org/10.1002/anie.201801848
State	Published - 4 May 2018

Bibliographical note

Funding Information:
This work was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under award numbers DE-FG03-98ER14879 (REC) and DE-FG02- 07ER15884 (JFS) and the US-Israel Bi-National Science Foundation under award number BSF-2014071.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

anions
ethylenedione
oxyallyl
photoelectron spectroscopy
quantum chemistry
radicals

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10.1002/anie.201801848

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@article{9ace0139c5db44f5acb7c8421cefffcc,

title = "Spectroscopy of Ethylenedione and Ethynediolide: A Reinvestigation",

abstract = "In an effort to characterize the electronic states of ethylenedione, OCCO, photoelectron-photofragment coincidence (PPC) spectroscopy was applied to measure anions at m/z 56 and 57 using a pulsed discharge of glyoxal vapor and N2O. PPC measurements at a photon energy of 3.20 eV yield photoelectron spectra in coincidence with either neutral photofragments or stable neutral products. The measurements showed that primarily stable neutral products were formed, with photoelectron spectra consistent with the oxyallyl diradical, C3H4O, and acetone enolate radical, C3H5O. The spectra were also found to have features nearly identical to those reported for OCCO and HOCCO by Sanov and co-workers. The stability of the neutral products, as well as an examination of spectra reported for the oxyallyl anion and acetone enolate show that the previous assignments of OCCO and HOCCO are in error, and are instead attributed here to the oxyallyl diradical, C3H4O, and the acetone enolate radical, C3H5O.",

keywords = "anions, ethylenedione, oxyallyl, photoelectron spectroscopy, quantum chemistry, radicals",

author = "Lunny, {Katharine G.} and Yanice Benitez and Yishai Albeck and Daniel Strasser and Stanton, {John F.} and Continetti, {Robert E.}",

note = "Funding Information: This work was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under award numbers DE-FG03-98ER14879 (REC) and DE-FG02- 07ER15884 (JFS) and the US-Israel Bi-National Science Foundation under award number BSF-2014071. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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month = may,

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doi = "10.1002/anie.201801848",

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T1 - Spectroscopy of Ethylenedione and Ethynediolide

T2 - A Reinvestigation

AU - Lunny, Katharine G.

AU - Benitez, Yanice

AU - Albeck, Yishai

AU - Strasser, Daniel

AU - Stanton, John F.

AU - Continetti, Robert E.

N1 - Funding Information: This work was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under award numbers DE-FG03-98ER14879 (REC) and DE-FG02- 07ER15884 (JFS) and the US-Israel Bi-National Science Foundation under award number BSF-2014071. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/5/4

Y1 - 2018/5/4

N2 - In an effort to characterize the electronic states of ethylenedione, OCCO, photoelectron-photofragment coincidence (PPC) spectroscopy was applied to measure anions at m/z 56 and 57 using a pulsed discharge of glyoxal vapor and N2O. PPC measurements at a photon energy of 3.20 eV yield photoelectron spectra in coincidence with either neutral photofragments or stable neutral products. The measurements showed that primarily stable neutral products were formed, with photoelectron spectra consistent with the oxyallyl diradical, C3H4O, and acetone enolate radical, C3H5O. The spectra were also found to have features nearly identical to those reported for OCCO and HOCCO by Sanov and co-workers. The stability of the neutral products, as well as an examination of spectra reported for the oxyallyl anion and acetone enolate show that the previous assignments of OCCO and HOCCO are in error, and are instead attributed here to the oxyallyl diradical, C3H4O, and the acetone enolate radical, C3H5O.

AB - In an effort to characterize the electronic states of ethylenedione, OCCO, photoelectron-photofragment coincidence (PPC) spectroscopy was applied to measure anions at m/z 56 and 57 using a pulsed discharge of glyoxal vapor and N2O. PPC measurements at a photon energy of 3.20 eV yield photoelectron spectra in coincidence with either neutral photofragments or stable neutral products. The measurements showed that primarily stable neutral products were formed, with photoelectron spectra consistent with the oxyallyl diradical, C3H4O, and acetone enolate radical, C3H5O. The spectra were also found to have features nearly identical to those reported for OCCO and HOCCO by Sanov and co-workers. The stability of the neutral products, as well as an examination of spectra reported for the oxyallyl anion and acetone enolate show that the previous assignments of OCCO and HOCCO are in error, and are instead attributed here to the oxyallyl diradical, C3H4O, and the acetone enolate radical, C3H5O.

KW - anions

KW - ethylenedione

KW - oxyallyl

KW - photoelectron spectroscopy

KW - quantum chemistry

KW - radicals

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 19

ER -

Spectroscopy of Ethylenedione and Ethynediolide: A Reinvestigation

Abstract

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