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Issue 12, 2013
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The curious case of (caffeine)·(benzoic acid): how heteronuclear seeding allowed the formation of an elusive cocrystal

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Abstract

Cocrystals are modular multicomponent solids with exceptional utility in synthetic chemistry and materials science. A variety of methods exist for the preparation of cocrystals, yet, some promising cocrystal phases have proven to be intractable synthetic targets. We describe a strategy for the synthesis of the pharmaceutically relevant (caffeine)·(benzoic acid) cocrystal (1), which persistently failed to form using a broad range of established techniques. State-of-the-art crystal structure prediction methods were employed to assess the possible existence of a thermodynamically stable form of 1, hence to identify appropriate heteronuclear seeds for cocrystallization. Once introduced, the designed heteronuclear seeds facilitated the formation of 1 and, significantly they (or seeds of the product cocrystal) continued to act as long-lasting laboratory “contaminants”, which encouraged cocrystal formation even when present at such low levels as to evade detection. The seeding technique described thus enables the synthesis of cocrystals regarded as unobtainable under desired conditions, and potentially signifies a new direction in the field of materials research.

Graphical abstract: The curious case of (caffeine)·(benzoic acid): how heteronuclear seeding allowed the formation of an elusive cocrystal

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Publication details

The article was received on 21 May 2013, accepted on 19 Aug 2013 and first published on 20 Aug 2013


Article type: Edge Article
DOI: 10.1039/C3SC51419F
Citation: Chem. Sci., 2013,4, 4417-4425
  • Open access: Creative Commons BY license
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    The curious case of (caffeine)·(benzoic acid): how heteronuclear seeding allowed the formation of an elusive cocrystal

    D. Bučar, G. M. Day, I. Halasz, G. G. Z. Zhang, J. R. G. Sander, D. G. Reid, L. R. MacGillivray, M. J. Duer and W. Jones, Chem. Sci., 2013, 4, 4417
    DOI: 10.1039/C3SC51419F

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