Making Co-CrystalsThe Utility of Ternary Phase Diagrams

Chiarella, Renato A.; Davey, Roger J.; Peterson, Matthew L.

doi:10.1021/cg070218y

Cited by 241 publications

(258 citation statements)

References 19 publications

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“…This was not entirely unexpected, as the isolation of pure cocrystal phases can require detailed understanding of the ternary phase diagrams for the acid, nicotinamide and the solvent; especially when narrow regions of stability exist for the pure cocrystal phase. 26 This work is currently underway and will be reported in a forthcoming publication. The ratio given is the acid : nicotinamide molar ratio in the solid mixture.…”

Section: Resultsmentioning

confidence: 99%

Cocrystals of Fenamic Acids with Nicotinamide

Fábián

Hamill

Eccles

et al. 2011

Crystal Growth & Design

105

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Access to the full text of the published version may require a subscription. flufenamic acid, niflumic acid, tolfenamic acid, mefenamic acid and meclofenamic acid was investigated using solution-based and solid-state preparation methods. It was anticipated that the wellknown acid-aromatic nitrogen heterosynthon would provide sufficient driving force for cocrystallization. The experiments yielded cocrystals with four of the five acids. Although the structures of these molecules are similar, they showed marked differences in both the stability and the stoichiometry of the cocrystals. A detailed analysis of the structures and properties of both the starting materials and the cocrystals allows tentative explanation of these differences, but it also shows that even though all four cocrystals utilize one of the most predictable supramolecular synthons (COOH…N), their structures and properties remain elusive to design. Rights

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Section: Resultsmentioning

confidence: 99%

Cocrystals of Fenamic Acids with Nicotinamide

Fábián

Hamill

Eccles

et al. 2011

Crystal Growth & Design

105

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“…A three-component phase diagram of the benzamide:dibenzyl sulfoxide cocrystal in water at 37 °C was constructed, based on methods previously described (Ainouz et al, 2009;Chiarella et al, 2007;Nehm et al, 2006), and is shown in Figure 9. The cocrystal solution equilibrium is described by…”

Section: Ternary Phase Diagrammentioning

confidence: 99%

Characterisation, solubility and intrinsic dissolution behaviour of benzamide: dibenzyl sulfoxide cocrystal

Grossjohann

Eccles

Maguire

et al. 2012

International Journal of Pharmaceutics

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This study examined the 1:1 cocrystal benzamide: dibenzyl sulfoxide, comprising the poorly water soluble dibenzyl sulfoxide (DBSO) and the more soluble benzamide (BA), to establish if this cocrystal shows advantages in terms of solubility and dissolution in comparison to its pure components and to a physical mixture. Solubility studies were performed by measuring DBSO solubility as a function of BA concentration, and a ternary phase diagram was constructed. Dissolution was examined through intrinsic dissolution studies. Solid-state characterisation was carried out by powder X-ray diffraction (PXRD), energy-dispersive X-ray diffraction (EDX), infra-red spectroscopy (ATR-FTIR) and thermal analysis. DBSO solubility was increased by means of complexation with BA. For the cocrystal, the solubility of both components was decreased in comparison to pure components. The cocrystal was identified as metastable and incongruently saturating. Dissolution studies revealed that dissolution of DBSO from the cocrystal was not enhanced in comparison to the pure compound or a physical mix, while BA release was retarded and followed square root of time kinetics. At the disk surface a layer of DBSO was found. The extent of complexation in solution can change the stability of the complex substantially. Incongruent solubility and dissolution behaviour of a cocrystal can result in no enhancement in the dissolution of the less soluble component and retardation of release of the more soluble component

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“…The liquid additive is, however, present in sufficiently small amounts for the system to thermodynamically behave as if it were solvent-free. 26 Consequently, LAG reactions are not affected by limitations of solubility that plague solution-phase reactivity 27 and mechanochemical screening can rapidly provide cocrystals based on starting materials that are too soluble for efficient cocrystallization from solution, or cocrystals of composition that is difficult to obtain by solution growth. The ability to efficiently conduct reactions in stoichiometric compositions that are not effective in solution has also been observed in organic mechanosynthesis.…”

Section: Mechanosynthesis In Organic Synthesis and Cocrystallizationmentioning

confidence: 99%

Clean and Efficient Synthesis Using Mechanochemistry: Coordination Polymers, Metal-Organic Frameworks and Metallodrugs

Friščić¹,

Halász²,

Štrukil³

et al. 2012

Croat. Chem. Acta

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Abstract. This review briefly discusses recent advances and future prospects in the mechanochemical synthesis of coordination compounds by ball milling and grinding, and highlights our contributions to the mechanosynthesis of porous metal-organic frameworks (MOFs) and zeolitic imidazolate frameworks (ZIFs), metal-organic pharmaceutical derivatives and metallodrugs using the recently developed mechanochemical methods of liquid-assisted grinding (LAG) and ion-and liquid-assisted grinding (ILAG). The role of mechanochemistry in the development of a solvent-free laboratory, cocrystal synthesis and new materials for luminescence and gas absorption is also highlighted. (doi: 10.5562/cca2014)

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Making Co-CrystalsThe Utility of Ternary Phase Diagrams

Abstract: We describe the use of ternary, isothermal phase diagrams of co-crystal-forming systems as a basis for understanding current crystallization methodologies and for experimental design in the preparation of co-crystals.

Cited by 241 publications

References 19 publications

Cocrystals of Fenamic Acids with Nicotinamide

Cocrystals of Fenamic Acids with Nicotinamide

Characterisation, solubility and intrinsic dissolution behaviour of benzamide: dibenzyl sulfoxide cocrystal

Clean and Efficient Synthesis Using Mechanochemistry: Coordination Polymers, Metal-Organic Frameworks and Metallodrugs

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