Issue 6, 2012

Observed and predicted hydrogen bond motifs in crystal structures of hydantoins, dihydrouracils and uracils

Abstract

A survey of crystal structures containing hydantoin, dihydrouracil and uracil derivatives in the Cambridge Structural Database revealed four main types of hydrogen bond motifs when derivatives with extra substituents able to interfere with the main motif are excluded. All these molecules contain two hydrogen bond donors and two hydrogen bond acceptors in the sequence of NH, C[double bond, length as m-dash]O, NH, and C[double bond, length as m-dash]O groups within a 5-membered ring (hydantoin) and two 6-membered rings (dihydrouracil and uracil). In all cases, both ring NH groups act as donors in the main hydrogen bond motif but there is an excess of hydrogen bond acceptors (two C[double bond, length as m-dash]O able to accept twice each) and so two possibilities are found: (i) each carbonyl O atom may accept one hydrogen bond or (ii) one carbonyl O atom may accept two hydrogen bonds while the other does not participate in the hydrogen bonding. We observed different preferences in the type and symmetry of the motifs adopted by the different derivatives, and a good agreement is found between motifs observed experimentally and those predicted using computational methods. We identified certain molecular factors such as chirality, substituent size and the possibility of C–H⋯O interactions as important factors influencing the motif observation.

Graphical abstract: Observed and predicted hydrogen bond motifs in crystal structures of hydantoins, dihydrouracils and uracils

Supplementary files

Article information

Article type
Paper
Submitted
23 Dec 2011
Accepted
04 Mar 2012
First published
22 Mar 2012

New J. Chem., 2012,36, 1347-1354

Observed and predicted hydrogen bond motifs in crystal structures of hydantoins, dihydrouracils and uracils

A. J. Cruz-Cabeza and C. H. Schwalbe, New J. Chem., 2012, 36, 1347 DOI: 10.1039/C2NJ21060F

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