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Issue 4, 2011
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Gas-phase H/D-exchange reactions on resorcinarene and pyrogallarene capsules: Proton transport through a one-dimensional Grotthuss mechanism

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Abstract

Hydrogen/deuterium exchange (HDX) experiments can be used to examine the gas-phase structure of hydrogen-bonded dimeric resorcinarene and pyrogallarene capsules. Already the qualitative comparison of the isotope exchange rates of different host–guest complexes with Cs+, tetramethyl ammonium (TMA+) and tetraethyl ammonium (TEA+) as the guest cations provides insight into the H/D-exchange mechanisms and with it, into the capsules' gas-phase ion structures. The smaller Cs+cations bind inside dimeric capsules with an intact seam of hydrogen bonds between the two monomers. Larger cations such as TEA+ lead to capsules with partially disrupted seams of hydrogen bonds. A fast isotope exchange is only observed, when the H-bonding seam between the two monomers is intact. In these cases, the H/D-exchange proceeds by a concerted mechanism reminiscent of the Grotthuss mechanism of proton transfer through water. Since it can only proceed along the seam, we refer to this exchange mechanism as a one dimensional Grotthuss mechanism.

Graphical abstract: Gas-phase H/D-exchange reactions on resorcinarene and pyrogallarene capsules: Proton transport through a one-dimensional Grotthuss mechanism

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Article information


Submitted
25 Oct 2010
Accepted
01 Dec 2010
First published
07 Jan 2011

Chem. Sci., 2011,2, 615-624
Article type
Edge Article

Gas-phase H/D-exchange reactions on resorcinarene and pyrogallarene capsules: Proton transport through a one-dimensional Grotthuss mechanism

H. D. F. Winkler, E. V. Dzyuba, J. A. W. Sklorz, N. K. Beyeh, K. Rissanen and C. A. Schalley, Chem. Sci., 2011, 2, 615
DOI: 10.1039/C0SC00539H

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