dc.contributor.author | McHugh, Charlene | |
dc.contributor.author | Erxleben, Andrea | |
dc.date.accessioned | 2014-01-21T16:17:15Z | |
dc.date.available | 2014-01-21T16:17:15Z | |
dc.date.issued | 2011 | |
dc.identifier.citation | McHugh, C,Erxleben, A (2011) 'Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N-6-Substituted Adenine'. Crystal Growth & Design, 11 :5096-5104. | en_US |
dc.identifier.uri | http://hdl.handle.net/10379/3987 | |
dc.description.abstract | Co-crystal and salt formation of the kinetin analogue N-6-benzyladenine with the pharmaceutically acceptable co-crystal and salt formers maleic acid, oxalic acid, glutaric acid, succinic acid, benzoic acid, and fumaric acid has been studied by solid-state and solvent-drop grinding in combination with X-ray powder diffraction. In all cases, salt or co-crystal formation was observed. Single crystals of (bzadeH(+))(mal(-)) (1) and (bzadeH(+))(2)(ox(2-)) (2) were obtained by solution crystallization, and their X-ray structures are reported along with that of (ade(H+))(2)(mal(-))(2).ade center dot 2H(2)O (3) (bzadeH(+) = N-6-benzyladeninium, adeH(+) = adeninium, ade = adenine, mal(-) = hydrogen maleate, ox(2-) = oxalate). The hydrogen-bonding motifs in 1-3 are discussed. The salts contain a robust bzadeH(+)-carboxylate or ade-carboxylate R-2(2)(9) heterosynthon involving the protonated Hoogsteen sites (N6-H, N7-H) of bzadeH(+) and ade. Molecular recognition between the protonated Hoogsteen site and the carboxylate group stabilizes the unusual 7H,9H tautomer of bzadeH(+) in 2 and the noncanonical 7H-adenine tautomer in 3. | en_US |
dc.format | application/pdf | en_US |
dc.language.iso | en | en_US |
dc.relation.ispartof | Crystal Growth & Design | en |
dc.rights | Attribution-NonCommercial-NoDerivs 3.0 Ireland | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/3.0/ie/ | |
dc.subject | Cyclin-dependent kinases | en_US |
dc.subject | Potassium hydrogen maleate | en_US |
dc.subject | Metal-oxalato frameworks | en_US |
dc.subject | Co-crystal formation | en_US |
dc.subject | Solid-state | en_US |
dc.subject | Gas-phase | en_US |
dc.subject | Noncovalent stabilization | en_US |
dc.subject | Molecular recognition | en_US |
dc.subject | 7H-adenine tautomer | en_US |
dc.subject | Inhibitory-activity | en_US |
dc.title | Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N-6-Substituted Adenine | en_US |
dc.type | Article | en_US |
dc.date.updated | 2013-11-01T17:22:32Z | |
dc.identifier.doi | http://dx.doi.org/10.1021/cg201007m | |
dc.local.publishedsource | http://dx.doi.org/10.1021/cg201007m | en_US |
dc.local.publisherstatement | This document is the unedited author's version of a Submitted Work that was subsequently accepted for publication in Crystal Growth and Design copyright © American Chemical Society after peer review. To access the final edited and published work, see http://dx.doi.org/10.1021/cg201007m | en_US |
dc.description.peer-reviewed | peer-reviewed | |
dc.contributor.funder | |~| | |
dc.internal.rssid | 1126361 | |
dc.local.contact | Andrea Erxleben, School Of Chemistry, Room 150, Arts/Science Building, Nui Galway. 2483 Email: andrea.erxleben@nuigalway.ie | |
dc.local.copyrightchecked | No | |
dc.local.version | ACCEPTED | |
nui.item.downloads | 769 | |