Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution

Ilaria Giannicchi, Benjamin Jouvelet, Benjamin Isare, Mathieu Linares, Antonella Dalla Cort, Laurent Bouteiller
2014 Chemical Communications  
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 bis-ureas self-association and of mono-ureas hydrogen bonding to strong HB acceptors. Notes and references
doi:10.1039/c3cc47447j pmid:24280764 fatcat:2snncrol7fcelibaji5ozsvrhu