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Direct Determination of Hydrogen-Bonded Structures in Resonant and Tautomeric Reactions Using Ultrafast Electron Diffraction

Srinivasan, Ramesh and Feenstra, Jonathan S. and Park, Sang Tae and Xu, Shoujun and Zewail, Ahmed H. (2004) Direct Determination of Hydrogen-Bonded Structures in Resonant and Tautomeric Reactions Using Ultrafast Electron Diffraction. Journal of the American Chemical Society, 126 (8). pp. 2266-2267. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20160817-132621187

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Abstract

We elucidate the keto−enol tautomeric equilibrium in acetylacetone, the structure of both keto and enol forms, and the nature of the intramolecular O−H···O HB in enolic acetylacetone using our ultrafast electron diffraction apparatus, thereby shedding new light on the nature of the hydrogen bond in resonant tautomeric structures. The enolic structure exhibits some π-resonance delocalization; however, this delocalization is not strong enough to give a symmetric skeletal geometry. The long O···O distance in the refined structure renders the homonuclear O−H···O hydrogen bond in acetylacetone localized and asymmetric.


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http://dx.doi.org/10.1021/ja031927cDOIArticle
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Additional Information:© 2004 American Chemical Society. Received December 23, 2003. Publication Date (Web): February 6, 2004. We thank Professor John D. Roberts and the three reviewers for helpful comments.
Record Number:CaltechAUTHORS:20160817-132621187
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160817-132621187
Official Citation:Direct Determination of Hydrogen-Bonded Structures in Resonant and Tautomeric Reactions Using Ultrafast Electron Diffraction Ramesh Srinivasan, Jonathan S. Feenstra, Sang Tae Park, Shoujun Xu, and Ahmed H. Zewail Journal of the American Chemical Society 2004 126 (8), 2266-2267 DOI: 10.1021/ja031927c
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:69712
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:17 Aug 2016 21:36
Last Modified:17 Aug 2016 21:36

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