Catalytic Effect of Solvent Vapors on the Spontaneous Formation of Caffeine–Malonic Acid Cocrystal

Title:
Catalytic Effect of Solvent Vapors on the Spontaneous Formation of Caffeine–Malonic Acid Cocrystal
Authors:
Ji, Canran; Hoffman, Mikaila C.; Mehta, Manish A. ( 0000-0001-7327-0245 )
Abstract:
Caffeine (a model pharmaceutical mimic) and malonic acid (a common excipient partner) are known to form a molecular cocrystal spontaneously over about 1 week when their powders are mixed at ambient conditions. We report the dramatic catalytic acceleration of this reaction when the mixture of powders is exposed to vapors of common laboratory solvents. Acetone and methanol vapors show rate enhancements over 1000-fold, effecting quantitative conversion in less than 5 min. The reaction progress was tracked ex situ by powder X-ray diffraction, and products were verified by C-13 solid-state NMR Our data show no evidence of an intermediate phase. Gravimetric experiments show that solvent vapor uptake is not stoichiometric and is reversible. This rare example of gas phase catalysis of supramolecular transformations has important implications for a deeper mechanistic understanding of diffusion controlled solid-solid reactions.
Citation:
Ji, Canran, Mikaila C. Hoffman, and Manish A. Mehta. 2017. "Catalytic Effect of Solvent Vapors on the Spontaneous Formation of Caffeine–Malonic Acid Cocrystal." Crystal Growth & Design 17(4): 1456-1459.
Publisher:
American Chemical Society
DATE ISSUED:
2017-04-05
Department:
Chemistry and Biochemistry
Type:
Article
PUBLISHED VERSION:
10.1021/acs.cgd.6b01164
Additional Links:
http://pubs.acs.org/doi/abs/10.1021/acs.cgd.6b01164
PERMANENT LINK:
http://hdl.handle.net/11282/620518

Full metadata record

DC FieldValue Language
dc.contributor.authorJi, Canranen
dc.contributor.authorHoffman, Mikaila C.en
dc.contributor.authorMehta, Manish A.en
dc.date.accessioned2017-09-14T17:40:00Z-
dc.date.available2017-09-14T17:40:00Z-
dc.date.issued2017-04-05-
dc.identifier.citationJi, Canran, Mikaila C. Hoffman, and Manish A. Mehta. 2017. "Catalytic Effect of Solvent Vapors on the Spontaneous Formation of Caffeine–Malonic Acid Cocrystal." Crystal Growth & Design 17(4): 1456-1459.en
dc.identifier.issn1528-7483-
dc.identifier.urihttp://hdl.handle.net/11282/620518-
dc.description.abstractCaffeine (a model pharmaceutical mimic) and malonic acid (a common excipient partner) are known to form a molecular cocrystal spontaneously over about 1 week when their powders are mixed at ambient conditions. We report the dramatic catalytic acceleration of this reaction when the mixture of powders is exposed to vapors of common laboratory solvents. Acetone and methanol vapors show rate enhancements over 1000-fold, effecting quantitative conversion in less than 5 min. The reaction progress was tracked ex situ by powder X-ray diffraction, and products were verified by C-13 solid-state NMR Our data show no evidence of an intermediate phase. Gravimetric experiments show that solvent vapor uptake is not stoichiometric and is reversible. This rare example of gas phase catalysis of supramolecular transformations has important implications for a deeper mechanistic understanding of diffusion controlled solid-solid reactions.en
dc.language.isoen_USen
dc.publisherAmerican Chemical Societyen
dc.identifier.doi10.1021/acs.cgd.6b01164-
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/acs.cgd.6b01164en
dc.subject.departmentChemistry and Biochemistryen_US
dc.titleCatalytic Effect of Solvent Vapors on the Spontaneous Formation of Caffeine–Malonic Acid Cocrystalen_US
dc.typeArticleen
dc.identifier.journalCrystal Growth & Designen
dc.subject.keywordSolid-state NMRen_US
dc.subject.keywordCo-crystalsen_US
dc.subject.keywordPharmaceutical cocrystalsen_US
dc.subject.keywordMechanochemical reactionsen_US
dc.subject.keywordClean synthesisen_US
dc.subject.keywordPicric aciden_US
dc.subject.keywordSpectroscopyen_US
dc.subject.keywordKineticsen_US
dc.subject.keywordTimeen_US
dc.identifier.volume17en_US
dc.identifier.issue4en_US
dc.identifier.startpage1456en_US
dc.rightsArchived with thanks to Crystal Growth & Designen
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