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

Henrik D. F. Winkler, Egor V. Dzyuba, Julian A. W. Sklorz, Ngong Kodiah Beyeh, Kari Rissanen, Christoph A. Schalley

Research output: Contribution to journalArticleScientificpeer-review

28 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)615-624
JournalChemical Science
Volume2
Issue number4
DOIs
Publication statusPublished - Jan 2011
MoE publication typeA1 Journal article-refereed

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