dc.contributor.author | O’Malley, Ciaran | |
dc.contributor.author | Bouchet, Chloe | |
dc.contributor.author | Manyara, Grayce | |
dc.contributor.author | Walsh, Niamh | |
dc.contributor.author | McArdle, Patrick | |
dc.contributor.author | Erxleben, Andrea | |
dc.date.accessioned | 2021-01-05T13:50:14Z | |
dc.date.issued | 2020-11-24 | |
dc.identifier.citation | O’Malley, Ciaran, Bouchet, Chloe, Manyara, Grayce, Walsh, Niamh, McArdle, Patrick, & Erxleben, Andrea. (2020). Salts, Binary and Ternary Cocrystals of Pyrimethamine: Mechanosynthesis, Solution Crystallization, and Crystallization from the Gas Phase. Crystal Growth & Design. doi:10.1021/acs.cgd.0c01147 | en_IE |
dc.identifier.issn | 1528-7505 | |
dc.identifier.uri | http://hdl.handle.net/10379/16407 | |
dc.description.abstract | A series of salts and binary and ternary cocrystals of the antimalaria drug pyrimethamine (PYR) are reported. PYR has a donor–acceptor–donor (DAD) and a donor–acceptor (DA) binding site, and cocrystallization experiments were performed with coformers with complementary acceptor-donor-acceptor (ADA) and acceptor-donor (AD) H-bonding functionalities. Three different preparation techniques were compared, namely, solution crystallization, crystallization from the gas phase, and liquid-assisted grinding. In several cases different solid-state forms were obtained depending on the crystallization method. The molecular ionic cocrystals PYRH+BAR–·PYR (BAR = barbituric acid) and (PYRH+SAC–)2·GLU (GLU = glutarimide, SAC = saccharin), the binary cocrystal PYR·GLU, the salt PYRH+NIC– (NIC = nicotinic acid), and two polymorphs of PYRH+SAC– could be crystallized by sublimation. Two other ternary molecular ionic cocrystals, (PYRH+BEN–)·PYR·SUC and (PYRH+SAC–)2·SOR (SUC = succinimide, BEN = benzoic acid, SOR = sorbic acid), were obtained by solution crystallization. Attempts to crystallize ternary cocrystals from solution also yielded a number of new two-component cocrystals including four new solvates of PYRH+SAC–, thus extending the structural landscape of the PYR/SAC system. Liquid-assisted milling was performed as a one-pot reaction and with the stepwise addition of the coformers. The (PYRH+SAC–)2·GLU cocrystal formed when the coformers were milled in one step and when they were added to the mill stepwise. For other systems the outcome of the two-step milling experiment depended on the order in which the coformers were added. The PYR-coformer interactions were analyzed using the PIXEL program. | en_IE |
dc.description.sponsorship | This publication has emanated from research supported in part by a research grant from Science Foundation Ireland (SFI) and is co-funded under the European Regional Development Fund under Grant Number 12/RC/2275. | en_IE |
dc.format | application/pdf | en_IE |
dc.language.iso | en | en_IE |
dc.publisher | American Chemical Society | en_IE |
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 | Salts | en_IE |
dc.subject | X-rays | en_IE |
dc.subject | Crystallization | en_IE |
dc.subject | Crystal structure | en_IE |
dc.subject | Oxygen | en_IE |
dc.title | Salts, binary and ternary cocrystals of pyrimethamine: mechanosynthesis, solution crystallization and crystallization from the gas phase | en_IE |
dc.type | Article | en_IE |
dc.date.updated | 2020-12-20T16:05:15Z | |
dc.identifier.doi | 10.1021/acs.cgd.0c01147 | |
dc.local.publishedsource | https://dx.doi.org/10.1021/acs.cgd.0c01147 | en_IE |
dc.description.peer-reviewed | peer-reviewed | |
dc.contributor.funder | Science Foundation Ireland | en_IE |
dc.contributor.funder | European Regional Development Fund | en_IE |
dc.description.embargo | 2021-11-24 | |
dc.internal.rssid | 24010660 | |
dc.local.contact | Andrea Erxleben, School Of Chemistry, Room 150, Arts/Science Building, Nui Galway. 2483 Email: andrea.erxleben@nuigalway.ie | |
dc.local.copyrightchecked | Yes | |
dc.local.version | ACCEPTED | |
dcterms.project | info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ | en_IE |
nui.item.downloads | 109 | |