Issue 11, 2010
From the journal:

CrystEngComm

Experimental and theoretical study of uracil derivatives: the crucial role of weak fluorine–fluorine noncovalent interactions†

Miquel Barceló-Oliver,*ab   Carolina Estarellas,a   Angel García-Raso,a   Angel Terrón,a   Antonio Frontera,*a   David Quiñonero,a   Ignasi Mata,c   Elies Molinsc  and  Pere M. Deyàa  

* Corresponding authors

a Departament de Química, Universitat de les Illes Balears, Crta. Valldemossa km 7.5, Palma de Mallorca, Spain
E-mail: miquel.barcelo@uib.es, toni.frontera@uib.es

b Institute of Inorganic Chemistry, University of Zürich, Winterthurerstrasse 190, Zürich, Switzerland

c Institut de Ciència dels Materials (CSIC), campus de la Universitat Autònoma, Cerdanyola del Vallés, Barcelona, Spain

Abstract

We have recently communicated the important role of lone pair–π, π–π and hydrophobic interactions in the solid architecture of 5-fluoro-1-hexyluracil and 1-hexyluracil (CrystEngComm, 2010, 12, 362–365). As a matter of fact, the simple substitution of a hydrogen atom by a fluorine atom has an enormous consequence in the solid state structure. It has been demonstrated that this is due to an increase in the π-acidity of the ring. In this article we extend the study to other uracil derivatives, where we have changed the hydrophobicity of the hexyl chain by introducing hydrophilic groups in the substituent, such as hydroxyl or carboxylic groups. The latter compounds, i.e. (N1-(3-hydroxypropyl)-5-fluorouracil and N1-(4-hydroxycarbonylbutyl)-5-fluorouracil monohydrate present interesting fluorine–fluorine interactions that are very important in determining the crystal packing.

Graphical abstract: Experimental and theoretical study of uracil derivatives: the crucial role of weak fluorine–fluorine noncovalent interactions

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C0CE00048E
Article type
Paper
Submitted
30 Mar 2010
Accepted
01 Jun 2010
First published
26 Jul 2010

CrystEngComm, 2010,12, 3758-3767

Permissions

Request permissions

Experimental and theoretical study of uracil derivatives: the crucial role of weak fluorine–fluorine noncovalent interactions

M. Barceló-Oliver, C. Estarellas, A. García-Raso, A. Terrón, A. Frontera, D. Quiñonero, I. Mata, E. Molins and P. M. Deyà, CrystEngComm, 2010, 12, 3758 DOI: 10.1039/C0CE00048E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements