Issue 1, 2005

Hydrogen bonds between ammonium ions and aromatic rings exist and have key consequences on solid-state and solution phase properties

Abstract

A very small azaphane that exhibits high affinity for H+ has been synthesised. Included protons are stabilised by a charge-assisted NH-π interaction and hence the bound proton is effectively solvated by the aromatic ring. Exchange of H+ is slow on the 1H NMR time scale and the conformational characteristics of the macrobicycle are highly pH dependent.

Graphical abstract: Hydrogen bonds between ammonium ions and aromatic rings exist and have key consequences on solid-state and solution phase properties

Supplementary files

Article information

Article type
Letter
Submitted
06 Oct 2004
Accepted
21 Oct 2004
First published
02 Dec 2004

New J. Chem., 2005,29, 64-67

Hydrogen bonds between ammonium ions and aromatic rings exist and have key consequences on solid-state and solution phase properties

C. A. Ilioudis, M. J. Bearpark and J. W. Steed, New J. Chem., 2005, 29, 64 DOI: 10.1039/B415532G

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