Capture of hydroxymethylene and its fast disappearance through tunnelling

Peter R. Schreiner (), Hans Peter Reisenauer, Frank C. Pickard Iv, Andrew C. Simmonett, Wesley D. Allen (), Edit Mátyus and Attila G. Császár
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Peter R. Schreiner: Institut für Organische Chemie der Justus-Liebig-Universität, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany
Hans Peter Reisenauer: Institut für Organische Chemie der Justus-Liebig-Universität, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany
Frank C. Pickard Iv: University of Georgia, Athens, Georgia 30602, USA
Andrew C. Simmonett: University of Georgia, Athens, Georgia 30602, USA
Wesley D. Allen: University of Georgia, Athens, Georgia 30602, USA
Edit Mátyus: Laboratory of Molecular Spectroscopy, Institute of Chemistry, Eötvös University, H-1518 Budapest 112PO Box 32, Hungary
Attila G. Császár: Laboratory of Molecular Spectroscopy, Institute of Chemistry, Eötvös University, H-1518 Budapest 112PO Box 32, Hungary

Nature, 2008, vol. 453, issue 7197, 906-909

Abstract: Hydroxymethylene: The brief life of a carbene Organic molecules with a carbon atom that forms only two bonds and contains two non-bonding valence electrons are known as carbenes. Many are highly reactive and have long been considered too short-lived for direct observations. Of these, hydroxymethylene (H–C–OH) is of particular interest as it is implicated in the photochemistry of formaldehyde and has been suggested to form carbohydrates in extraterrestrial environments. It had never been observed, but now hydroxymethylene has been synthesized, then trapped in an argon matrix at 11 K. Even in these conditions it rearranges with a half-life of just 2 hours to form formaldehyde, using a mechanism involving rapid hydrogen tunnelling. This means that hydroxymethylene is unlikely to be identified spectroscopically or to be around long enough to be involved in the formation of sugars in space.

Date: 2008
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DOI: 10.1038/nature07010

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