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Concerning the Role of Supercritical Carbon Dioxide in SN1 Reactions

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Qiao,  Yunxiang
Service Department Theyssen (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Theyssen,  Nils
Service Department Theyssen (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Francio,  Giancarlo
Service Department Leitner (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leitner,  Walter
Institut für Technische und Makromolekulare Chemie RWTH Aachen University, Worringerweg 1, 52074 Aachen (Germany);
Research Group Leitner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Reetz,  Manfred T.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Department of Chemistry, Philipps-Universitt Marburg Hans-Meerwein-Straße, 35032 Marburg (Germany);

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Citation

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.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002C-817A-C
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.