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  Concerning the Role of Supercritical Carbon Dioxide in SN1 Reactions

Qiao, Y., Theyssen, N., Eifert, T., Liauw, M. A., Francio, G., Schenk, K., et al. (2017). Concerning the Role of Supercritical Carbon Dioxide in SN1 Reactions. Chemistry – A European Journal, 23(16), 3898-3902. doi:10.1002/chem.201604151.

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 Creators:
Qiao, Yunxiang1, Author              
Theyssen, Nils1, Author              
Eifert , Tobias2, Author
Liauw, Marcel A.2, Author
Francio, Giancarlo3, Author              
Schenk , Karolin2, Author
Leitner, Walter2, 4, Author              
Reetz, Manfred T.5, 6, Author              
Affiliations:
1Service Department Theyssen (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445632              
2Institut für Technische und Makromolekulare Chemie RWTH Aachen University, Worringerweg 1, 52074 Aachen (Germany), ou_persistent22              
3Service Department Leitner (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445626              
4Research Group Leitner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445610              
5Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445588              
6Department of Chemistry, Philipps-Universitt Marburg Hans-Meerwein-Straße, 35032 Marburg (Germany), ou_persistent22              

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Free keywords: carbon dioxide; solvent effects; solvolysis; supercritical fluids; sustainable chemistry
 Abstract: A series of SN1-type reactions has been studied under various conditions to clarify the role of supercritical carbon dioxide (scCO2) as reaction medium for this kind of transformations. The application of scCO2 did not result in higher yields in any of the experiments in comparison to those under neat conditions or in the presence of other inert compressed gases. High-pressure UV/Vis spectroscopic measurements were carried out to quantify the degree of carbocation formation of a highly SN1-active alkyl halide as a function of the applied solvent. No measureable concentration of carbocations could be detected in scCO2, just like in other low polarity solvents. Taken together, these results do not support the previously claimed activating effect via enhanced SN1 ionization due to the quadrupolar moment of the supercritical fluid.

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Language(s): eng - English
 Dates: 2017-02-202017-03-17
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201604151
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Alternative Title : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 23 (16) Sequence Number: - Start / End Page: 3898 - 3902 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058