Engineering short, strong hydrogen bonds in urea di-carboxylic acid complexes

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dc.contributor.authorJones, AOFen_AU
dc.contributor.authorLeech, CKen_AU
dc.contributor.authorMcIntyre, GJen_AU
dc.contributor.authorWilson, CCen_AU
dc.contributor.authorThomas, LHen_AU
dc.date.accessioned2016-09-06T00:53:15Zen_AU
dc.date.available2016-09-06T00:53:15Zen_AU
dc.date.issued2014-04-17en_AU
dc.date.statistics2016-09-06en_AU
dc.description.abstractA series of seven 2:1 molecular complexes of urea (U) and methyl ureas with di-carboxylic acids (A) are reported, along with the results of their study by variable temperature diffraction. These all contain short, strong O–H⋯O hydrogen bonds and a recurring acid⋯amide heterodimer forming U–A–U synthons. Despite differences in the degree of saturation of the linking C–C groups of the di-carboxylic acids and the single or double methyl substitution of one of the N atoms of the urea, the packing arrangements are remarkably similar in five of the complexes; the exceptions being N-methylurea oxalic acid and N,N-dimethylurea fumaric acid. The five similar molecular complexes all show contraction of one unit cell parameter on increasing temperature due to rearrangements of the weaker interactions which hold together the U–A–U units. The strength of the short, strong O–H⋯O hydrogen bond is shown to be linked both to the length of the connecting bridge between the carboxylic acid groups of the acid, and to the ΔpKa values between the two components. ©, 2014, The Royal Society of Chemistry.en_AU
dc.identifier.citationJones, A. O. F., Leech, C. K., McIntyre, G. J., Wilson, C. C., & Thomas, L. H. (2014). Engineering short, strong hydrogen bonds in urea di-carboxylic acid complexes. [10.1039/C4CE00587B]. CrystEngComm, 16(35), 8177-8184. doi:10.1039/c4ce00587ben_AU
dc.identifier.govdoc7059en_AU
dc.identifier.issn2046-2069en_AU
dc.identifier.issue35en_AU
dc.identifier.journaltitleCrystEngCommen_AU
dc.identifier.pagination8177-8184en_AU
dc.identifier.urihttp://dx.doi.org/10.1039/c4ce00587ben_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/7457en_AU
dc.identifier.volume16en_AU
dc.language.isoenen_AU
dc.publisherRoyal Society of Chemistryen_AU
dc.subjectMolecular structureen_AU
dc.subjectTemperature dependenceen_AU
dc.subjectHydrogenen_AU
dc.subjectDicarboxylic acidsen_AU
dc.subjectAtom collisionsen_AU
dc.subjectFumaric aciden_AU
dc.titleEngineering short, strong hydrogen bonds in urea di-carboxylic acid complexesen_AU
dc.typeJournal Articleen_AU
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