Show simple item record

dc.contributor.authorPortalone, Gustavo
dc.contributor.authorRissanen, Kari
dc.date.accessioned2018-10-03T12:26:58Z
dc.date.issued2018fi
dc.identifier.citationPortalone, G., & Rissanen, K. (2018). Multifacial Recognition in Binary and Ternary Cocrystals from 5-Halouracil and Aminoazine Derivatives. <em>Crystal Growth and Design</em>, 18 (10), 5904-5918. <a href="https://doi.org/10.1021/acs.cgd.8b00662">doi:10.1021/acs.cgd.8b00662</a>fi
dc.identifier.otherTUTKAID_78725
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/59755
dc.description.abstractA systematic analysis using single crystal X-ray diffraction was performed to explore the role exerted by potential intercomponent proton-transfer reactions in the supramolecular structures of A–B cocrystals formed by 5-haloderivatives of uracil (A), coupled with 2-aminoadenine simulants (aminoazines, B). Twelve new heterodimers were synthesized in different stoichiometries and cocrystallized by solvent cogrinding followed by solution crystallization. In the binary cocrystals, uracil or 1-methyluracil with halide modification at the 5 position (F, Cl, Br, I) was coupled with amino-aromatic N-heterocycles (melamine, 2,4,6-triaminopyrimidine, 2,6-diaminopyridine) as a multivalent site for pyrimidine nucleobase recognition. The crystallographic analysis showed that, next to the expected neutral three-point hydrogen bonds (TPI), ionized TPI, favored by A → B proton transfer, can be used for WC multifacial recognition. Noteworthy, the formation of the charged TPI, which depends on the acid/base properties of the components, always takes place between the more acidic site of the 5-halonucleobases (N3 atom) and the more basic site (imino N atom) of 2,4,6-triaminopyrimidine or 2,6-diaminopyridine, and melamine recognition unit results in being insufficiently basic to accept a proton. The general ability of pyrimidine nucleobases to provide electron donating groups to halogen bonding has been confirmed in seven cocrystals containing the 5-chloro, 5-bromo, or 5-iododerivatives coupled with melamine or 2,4,6-triaminopyrimidine. Considerations of the relative acidities of coformers A and of the relative basicities of coformers B allowed us to design and characterize by single-crystal X-ray diffraction the first ternary pyrimidine nucleobase-containing cocrystal based on the JANUS-WEDGE concept: the nucleobase–Janus–nucleobase (1:1:1) triad showing a 2,4,6-triamino pyrimidine molecule wedged via neutral and ionized TPI between the 5-fluorouracil/1-methyluracil pair in reverse WC fashion.fi
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.ispartofseriesCrystal Growth and Design
dc.rightsIn Copyright
dc.subject.otherhalogen bondingfi
dc.subject.othersingle crystal X-raysfi
dc.titleMultifacial Recognition in Binary and Ternary Cocrystals from 5-Halouracil and Aminoazine Derivativesfi
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-201810034333
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemia
dc.date.embargo2019-09-05
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.date.updated2018-10-03T12:15:14Z
dc.description.reviewstatuspeerReviewed
dc.format.pagerange5904-5918
dc.relation.issn1528-7483
dc.relation.numberinseries10
dc.relation.volume18
dc.type.versionFinal Draft
dc.rights.copyright© 2018 American Chemical Society
dc.rights.accesslevelopenAccessfi
dc.format.contentfulltext
dc.rights.urlhttp://rightsstatements.org/page/InC/1.0/?language=en
dc.relation.doi10.1021/acs.cgd.8b00662


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record

In Copyright
Except where otherwise noted, this item's license is described as In Copyright