One ring to bind them all: shape-selective complexation of phenylenediamine isomers with cucurbit[6]uril in the gas phase

The Journal of Physical Chemistry. a
David V DeardenMartin F Jarrold

Abstract

We examined complexes between cucurbit[6]uril and each of ortho-, meta-, and para-phenylenediamine using computational methods, Fourier transform ion cyclotron resonance mass spectrometry, and ion mobility spectrometry. These fundamental gas phase studies show that the lowest energy binding sites for ortho- and meta-phenylenediamine are on the exterior of cucurbit[6]uril, whereas para-phenylenediamine preferentially binds in the interior, in a pseudorotaxane fashion. This conclusion is based on reactivity of each of the complexes with tert-butylamine, where the ortho- and meta-phenylenediamine complexes exchange with tert-butylamine, whereas the para-phenylenediamine complex undergoes two slow additions without displacement. Further, under sustained off-resonance irradiation conditions, the ortho- and meta-phenylenediamine complexes fragment easily via losses of neutral phenylenediamine, whereas the para-phenylenediamine complex fragments at higher energies primarily via cleavage of covalent bonds in the cucurbituril. Finally, ion mobility studies show ion populations for the ortho- and meta-phenylenediamine complexes that primarily have collision cross sections consistent with external complexation, whereas the para-phenylened...Continue Reading

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Citations

Aug 7, 2012·Journal of the American Society for Mass Spectrometry·Tae Su ChoiHugh I Kim
Jan 18, 2014·Journal of the American Society for Mass Spectrometry·Dong Hun NohHugh I Kim
Jul 8, 2015·Organic & Biomolecular Chemistry·De-Qing ZhangJing-Xin Liu
Apr 24, 2013·Nature Chemistry·Tung-Chun LeeWerner M Nau
Feb 27, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Martin F Czar, Rebecca A Jockusch
Nov 16, 2019·Beilstein Journal of Organic Chemistry·Anniina KiesiläElina Kalenius
May 18, 2010·Organic Letters·Xiaoxi LingEric Masson
Oct 8, 2015·Journal of the American Society for Mass Spectrometry·Ekaterina KovalenkoVladimir P Fedin
Oct 4, 2017·Journal of the American Society for Mass Spectrometry·Glenn CarroyPascal Gerbaux
Apr 12, 2011·Organic Letters·José P Da SilvaV Ramamurthy
Mar 12, 2015·The Journal of Physical Chemistry. B·Jong Wha LeeHugh I Kim
Nov 19, 2020·The Journal of Physical Chemistry. a·Sota TainakaYoshiya Inokuchi

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