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Issue 18, 2019
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Alkyl substituted 4-pyrrolidinopyridinium salts encapsulated in the cavity of cucurbit[10]uril

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Abstract

The interaction between cucuribit[10]uril (Q[10]) and a series of 4-pyrrolidinopyridinium salts bearing aliphatic substituents at the pyridinium nitrogen, namely 4-(C4H8N)C5H5NRBr, where R = Et (g1), n-butyl (g2), n-pentyl (g3), n-hexyl (g4), n-octyl (g5), n-dodecyl (g6), has been studied in aqueous solution by 1H NMR spectroscopy, electronic absorption spectroscopy and mass spectrometry. The results revealed that the guests g1–g5 are located completely inside the cavity differing only in the orientation of g1, g4 and g5 which are aligned with the portal, whilst g2 and g3 are perpendicular to it. For g6, the tetrahydropyrrole moiety remains outside of the portal. DFT calculations confirm the stability of the guests in the Q[10] and the possibility of their curved structure inside the Q[10].

Graphical abstract: Alkyl substituted 4-pyrrolidinopyridinium salts encapsulated in the cavity of cucurbit[10]uril

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Supplementary files

Article information


Submitted
01 Mar 2019
Accepted
08 Apr 2019
First published
10 Apr 2019

New J. Chem., 2019,43, 7028-7034
Article type
Paper

Alkyl substituted 4-pyrrolidinopyridinium salts encapsulated in the cavity of cucurbit[10]uril

W. Xu, M. Liu, M. C. Escaño, C. Redshaw, B. Bian, Y. Fan, Z. Tao and X. Xiao, New J. Chem., 2019, 43, 7028
DOI: 10.1039/C9NJ01089K

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