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Concerted or Stepwise: How Much Do Free-Energy Landscapes Tell Us about the Mechanisms of Elimination Reactions?
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Computational and Systems Biology.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Computational and Systems Biology.
2014 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 79, no 3, 1280-1288 p.Article in journal (Refereed) Published
Abstract [en]

The base-catalyzed dehydration of benzene cis-1,2-dihydrodiols is driven by formation of an aromatic product as well as intermediates potentially stabilized by hyperaromaticity. Experiments exhibit surprising shifts in isotope effects, indicating an unusual mechanistic balance on the E2-E1cB continuum. In this study, both land 2-dimensional free energy surfaces are generated for these compounds with various substituents, using density functional theory and a mixed implicit/explicit solvation model. The computational data help unravel hidden intermediates along the reaction coordinate and provide a novel conceptual framework for distinguishing between competing pathways in this and any other system with borderline reaction mechanisms.

Place, publisher, year, edition, pages
2014. Vol. 79, no 3, 1280-1288 p.
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Natural Sciences
Identifiers
URN: urn:nbn:se:uu:diva-220989DOI: 10.1021/jo402702mISI: 000331163800047OAI: oai:DiVA.org:uu-220989DiVA: diva2:707680
Funder
Swedish National Infrastructure for Computing (SNIC), 2013/26-1
Available from: 2014-03-25 Created: 2014-03-24 Last updated: 2017-12-05

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Duarte, FernandaKamerlin, Shina Caroline Lynn

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