uu.seUppsala University Publications
Change search
ReferencesLink to record
Permanent link

Direct link
Superacid-Promoted Ionization of Alkanes Without Carbonium Ion Formation: A Density Functional Theory Study
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
2012 (English)In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 116, no 40, 9979-9984 p.Article in journal (Refereed) Published
Abstract [en]

The carbonium ion has been suggested to be the intermediate in superacid-promoted reactions (SbF5-HF) such as hydrogen-deuterium exchange and in the electrophilic C-H cleavage into hydrogen and the carbenium ion. In this study, the superacid-promoted C-H cleavage into hydrogen and the carbenium ion was studied using density functional theory (B3LYP and M062X) and ab initio methods (MP2 and CCSD). The calculations suggest that the superacid-promoted C-H cleavage proceeds via a concerted transition state leading to hydrogen (H-2) and the carbenium ion without the formation of the elusive carbonium ion. The reactivity for the superacid promoted C-H cleavage decreases upon going from isobutane (tertiary) > propane (secondary) > isobutane (primary) > propane (primary) > ethane >> methane.

Place, publisher, year, edition, pages
2012. Vol. 116, no 40, 9979-9984 p.
National Category
Organic Chemistry Theoretical Chemistry
URN: urn:nbn:se:uu:diva-181675DOI: 10.1021/jp306319sISI: 000309648800023OAI: oai:DiVA.org:uu-181675DiVA: diva2:557357
Available from: 2012-09-27 Created: 2012-09-27 Last updated: 2013-03-07Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full texthttp://pubs.acs.org/doi/abs/10.1021/jp306319s

Search in DiVA

By author/editor
Dinér, Peter
By organisation
Synthetical Organic Chemistry
In the same journal
Journal of Physical Chemistry A
Organic ChemistryTheoretical Chemistry

Search outside of DiVA

GoogleGoogle Scholar
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Altmetric score

Total: 348 hits
ReferencesLink to record
Permanent link

Direct link