Gas-phase Structure Determination Of Dihydroxycarbene, One Of The Smallest Stable Singlet Carbenes

Womack, Carrie

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https://hdl.handle.net/2142/50904 Copy

Description

Title

Gas-phase Structure Determination Of Dihydroxycarbene, One Of The Smallest Stable Singlet Carbenes

Author(s)

Womack, Carrie

Contributor(s)

• McCarthy, Michael C.
• Stanton, John F.
• Field, Robert W.
• Martinez, Oscar, Jr.
• McCaslin, Laura
• Crabtree, Kyle N.

Issue Date

2014-06-16

Keyword(s)

Mini-symposium: Spectroscopy in Kinetics and Dynamics

Abstract

"Carbenes (R$_{1}$-C-R$_{2}$) are a reactive class of compounds, usually characterized by an electron-deficient divalent carbon atom, found in applications ranging from organic synthesis to gas phase oxidation chemistry. Carbenes with 2- or 3-atom substituents often undergo rapid unimolecular isomerization, but may be stabilized if these substituents are electron-donating. Dihydroxycarbene (HO-\""{C}-OH) is one of the smallest singlet carbenes to be afforded this stability, due to its two electron-donating hydroxyl groups. We report the first gas-phase detection and structural characterization of this reactive species, using a combination of Fourier transform microwave spectroscopy and high level electronic structure calculations. Detection in the gas phase indicates that it is fairly stable relative to its isomers, formic acid (HCOOH) and the simplest Criegee intermediate (CH$_2$OO), the latter of which has recently received a great deal of attention for its role in the atmospheric ozonolysis of alkenes. Our experimental results yield a precise structure of HO-\""{C}-OH, and we comment on upcoming experiments investigating its stability and reactivity with other common atmospheric species."

Publisher

International Symposium on Molecular Spectroscopy

Type of Resource

text

Language

English

Permalink

http://hdl.handle.net/2142/50904

DOI

https://doi.org/10.15278/isms.2014.MH10

Copyright and License Information

Copyright 2014 by the authors. Licensed under a Creative Commons Attribution 4.0 International License. http://creativecommons.org/licenses/by/4.0/

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