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A tetrahydrofuran (THF) solution of the mechanochemical product prepared using EtOH as additive led to a single crystal of the same material obtained by mechanochemistry, which was used for crystal structure determination at 100\u2005K. Powder X-ray diffraction ruled out crystallographic phase transitions in the 100\u2013295\u2005K interval. Neat mechanical treatment (in a mortar and pestle, or in a ball mill at 20 or 30\u2005Hz milling frequencies) gave rise to an amorphous phase, as shown by powder X-ray diffraction; however, FT\u2013IR spectroscopy unambiguously indicates that a mechanochemical reaction has occurred. Neat milling the reactants at 10 and 15\u2005Hz led to incomplete reactions. Thermogravimetry and differential scanning calorimetry indicate that the amorphous and crystalline mechanochemical products form glasses\/supercooled liquids before melting, and do not recrystallize upon cooling. However, the amorphous material obtained by neat grinding crystallizes upon storage into the salt reported. The mechanochemical synthesis, crystal structure analysis, Hirshfeld surfaces, powder X-ray diffraction, thermogravimetry, differential scanning calorimetry, FT\u2013IR spectroscopy, and aqueous solubility of quininium aspirinate are herein reported.<\/jats:p>","DOI":"10.1107\/s2053229621008275","type":"journal-article","created":{"date-parts":[[2021,8,25]],"date-time":"2021-08-25T17:17:23Z","timestamp":1629911843000},"page":"566-576","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":4,"title":["Mechanochemical synthesis insights and solid-state characterization of quininium aspirinate, a glass-forming drug\u2013drug salt"],"prefix":"10.1107","volume":"77","author":[{"given":"Nehemiah","family":"Harris","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jubilee","family":"Benedict","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Diane A.","family":"Dickie","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2083-7599","authenticated-orcid":true,"given":"Silvina","family":"Pagola","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2021,8,25]]},"reference":[{"key":"ep3016_bb1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/1475-2875-10-144","volume":"10","author":"Achan","year":"2011","journal-title":"Malar. 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