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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
Subject(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.
Issue Date:2014-06-16
Publisher:International Symposium on Molecular Spectroscopy
Citation Info:Womack, C.; McCarthy, M.C.; Stanton, J.F.; Field, R.W.; Martinez Jr., O.; McCaslin, L.; Crabtree, K.N. GAS-PHASE STRUCTURE DETERMINATION OF DIHYDROXYCARBENE, ONE OF THE SMALLEST STABLE SINGLET CARBENES. Proceedings of the International Symposium on Molecular Spectroscopy, Urbana, IL, June 16-21, 2014. DOI: 10.15278/isms.2014.MH10
Rights Information:Copyright 2014 by the authors. Licensed under a Creative Commons Attribution 4.0 International License.
Date Available in IDEALS:2014-09-17

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