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Issue 5, 2014
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Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution

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Abstract

The phenylurea moiety is a ubiquitous synthon in supramolecular chemistry. Here we report that the introduction of chlorine or bromine atoms in the ortho positions to the urea unit is a simple and very efficient way to improve its intermolecular hydrogen bond (HB) donor character. This effect was demonstrated in solution both in the context of self-association of bis-ureas and hydrogen bonding of mono-ureas to strong HB acceptors.

Graphical abstract: Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution

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Article information


Submitted
29 Sep 2013
Accepted
04 Nov 2013
First published
05 Nov 2013

Chem. Commun., 2014,50, 611-613
Article type
Communication

Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution

I. Giannicchi, B. Jouvelet, B. Isare, M. Linares, A. Dalla Cort and L. Bouteiller, Chem. Commun., 2014, 50, 611
DOI: 10.1039/C3CC47447J

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