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.
Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution / Giannicchi, Ilaria; Benjamin, Jouvelet; Benjamin, Isare; Mathieu, Linares; DALLA CORT, Antonella; Laurent, Bouteiller. - In: CHEMICAL COMMUNICATIONS. - ISSN 1359-7345. - STAMPA. - 50:5(2014), pp. 611-613. [10.1039/c3cc47447j]
Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution
GIANNICCHI, ILARIA;DALLA CORT, Antonella;
2014
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
