Hydrogen-Deuterium Exchange in Basic Near-Critical and Supercritical Media: An Experimental and Theoretical Study

The Journal of Physical Chemistry. a
Pia R AlburquerqueTolga N V Karsili

Abstract

Treatment of homo- and heterocyclic aromatic substrates with basic deuterium oxide under near- or supercritical conditions results in rapid base-catalyzed hydrogen-deuterium exchange (HDE) in aromatic and benzylic positions. It has been postulated that HDE follows a simple deprotonation-reprotonation mechanism, but little evidence has been provided to date. This study correlates experimentally observed proton exchanges in n-butylbenzene with ab initio calculations of the acidities and potential energy (PE) profiles. In addition to providing further support for carbanion intermediacy in HDE, these results offer new insights into substrate acidities in near- and supercritical aqueous media and the optimal conditions required for their isotope exchange.

References

May 17, 2011·Physical Chemistry Chemical Physics : PCCP·A P Harding, P L A Popelier
Dec 17, 2014·Proceedings of the National Academy of Sciences of the United States of America·Lu WangThomas E Markland

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