Hydrogen tunneling avoided: enol-formation from a charge-tagged phenyl pyruvic acid derivative evidenced by tandem-MS, IR ion spectroscopy and theory-Reference-Cited by-同舟云学术

Hydrogen tunneling avoided: enol-formation from a charge-tagged phenyl pyruvic acid derivative evidenced by tandem-MS, IR ion spectroscopy and theory

Published:2019 Issue:30 Volume:21 Page:16591-16600
ISSN:1463-9076
Container-title:Physical Chemistry Chemical Physics
language:en
Short-container-title:Phys. Chem. Chem. Phys.

Author:

Paul Mathias¹²³⁴^ORCID,Peckelsen Katrin¹²³⁴,Thomulka Thomas¹²³⁴,Neudörfl Jörg¹²³⁴^ORCID,Martens Jonathan⁵⁶⁷⁸⁹^ORCID,Berden Giel⁵⁶⁷⁸⁹^ORCID,Oomens Jos⁵⁶⁷⁸⁹^ORCID,Berkessel Albrecht¹²³⁴^ORCID,Meijer Anthony J. H. M.¹⁰²¹¹¹²^ORCID,Schäfer Mathias¹²³⁴^ORCID

Affiliation:

1. University of Cologne

2. Department of Chemistry

3. 50939 Köln

4. Germany

5. Radboud University

6. Institute for Molecules and Materials

7. FELIX Laboratory

8. 6525 ED Nijmegen

9. The Netherlands

10. University of Sheffield

11. Sheffield S3 7HF

12. UK

Abstract

A charge-tagged hydroxycarbene formed via tandem-MS delivers exclusively enol-tautomers and avoids quantum mechanical hydrogen tunneling in the gas phase.

Funder

Deutsche Forschungsgemeinschaft

Horizon 2020 Framework Programme

Publisher

Royal Society of Chemistry (RSC)

Subject

Physical and Theoretical Chemistry,General Physics and Astronomy

Link

http://pubs.rsc.org/en/content/articlepdf/2019/CP/C9CP02316J

Reference44 articles.

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4. Umpolung by N-Heterocyclic Carbenes: Generation and Reactivity of the Elusive 2,2-Diamino Enols (Breslow Intermediates)

5. Characterization of the Key Intermediates of Carbene-Catalyzed Umpolung by NMR Spectroscopy and X-Ray Diffraction: Breslow Intermediates, Homoenolates, and Azolium Enolates

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