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

The curious case of (caffeine).(benzoic acid): how heteronuclear seeding allowed the formation of an elusive cocrystal
The curious case of (caffeine).(benzoic acid): how heteronuclear seeding allowed the formation of an elusive cocrystal
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, and to identify appropriate heteronuclear seeds for corystallization. Once introduced, the designed heteronuclear seeds facilitated the formation of 1 and, significantly, 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.
1478-6524
4417-4425
Bucar, Dejan-Kresimir
bc6773f5-d0fc-453a-ace7-e4f969fae8b4
Day, Graeme Matthew
e3be79ba-ad12-4461-b735-74d5c4355636
Halasz, Ivan
6b64d206-f49c-40b4-8a8b-a34eb2be6346
Zhang, Geoff G.Z.
2329626d-dbe0-48fc-a62d-9229a50c74f0
Sander, John R.G.
b33cd8f9-2999-404e-92d1-c5fee3c8af17
Reid, David G.
0d06f1c4-82d5-4c93-af16-92e236df84e7
MacGillivray, Leonard R.G.
f08986e9-1146-439c-abc9-b256d23b9361
Duer, Melinda J.
10ebfcb5-5bf7-466c-af5a-a34d8534a959
Jones, William
3173abf0-1cfa-45f0-996e-2586b385c21e
Bucar, Dejan-Kresimir
bc6773f5-d0fc-453a-ace7-e4f969fae8b4
Day, Graeme Matthew
e3be79ba-ad12-4461-b735-74d5c4355636
Halasz, Ivan
6b64d206-f49c-40b4-8a8b-a34eb2be6346
Zhang, Geoff G.Z.
2329626d-dbe0-48fc-a62d-9229a50c74f0
Sander, John R.G.
b33cd8f9-2999-404e-92d1-c5fee3c8af17
Reid, David G.
0d06f1c4-82d5-4c93-af16-92e236df84e7
MacGillivray, Leonard R.G.
f08986e9-1146-439c-abc9-b256d23b9361
Duer, Melinda J.
10ebfcb5-5bf7-466c-af5a-a34d8534a959
Jones, William
3173abf0-1cfa-45f0-996e-2586b385c21e

Bucar, Dejan-Kresimir, Day, Graeme Matthew, Halasz, Ivan, Zhang, Geoff G.Z., Sander, John R.G., Reid, David G., MacGillivray, Leonard R.G., Duer, Melinda J. and Jones, William (2013) The curious case of (caffeine).(benzoic acid): how heteronuclear seeding allowed the formation of an elusive cocrystal. Chemical Science, 4 (12), 4417-4425. (doi:10.1039/C3SC51419F).

Record type: Article

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, and to identify appropriate heteronuclear seeds for corystallization. Once introduced, the designed heteronuclear seeds facilitated the formation of 1 and, significantly, 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.

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e-pub ahead of print date: 20 August 2013
Published date: 1 December 2013
Organisations: Chemistry

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Local EPrints ID: 356200
URI: https://eprints.soton.ac.uk/id/eprint/356200
ISSN: 1478-6524
PURE UUID: 32a7abff-513e-4865-adde-b7b40b5ef4a9
ORCID for Graeme Matthew Day: ORCID iD orcid.org/0000-0001-8396-2771

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Date deposited: 11 Sep 2013 12:58
Last modified: 06 Jun 2018 12:28

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Contributors

Author: Dejan-Kresimir Bucar
Author: Ivan Halasz
Author: Geoff G.Z. Zhang
Author: John R.G. Sander
Author: David G. Reid
Author: Leonard R.G. MacGillivray
Author: Melinda J. Duer
Author: William Jones

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