A Red Zwitterionic Co-Crystal of Acetaminophen and 2,4-Pyridinedicarboxylic Acid

John R.G Sander; Dejan-Krešimir Bučar; Rodger F Henry; Jonas Baltrusaitis; Geoff G.Z Zhang; Leonard R Macgillivray

doi:10.1002/jps.22229

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A Red Zwitterionic Co-Crystal of Acetaminophen and 2,4-Pyridinedicarboxylic Acid

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A Red Zwitterionic Co-Crystal of Acetaminophen and 2,4-Pyridinedicarboxylic Acid

John R.G Sander, Dejan-Krešimir Bučar, Rodger F Henry, Jonas Baltrusaitis, Geoff G.Z Zhang and Leonard R Macgillivray

Journal of pharmaceutical sciences, Vol.99(9), pp.3676-3683

09/2010

DOI: 10.1002/jps.22229

PMID: 20574998

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Abstract

We report on a co-crystal of acetaminophen (APAP) and 2,4-pyridinedicarboxylic acid (PDA). The co-crystal was discovered by screening using the solution-mediated phase transformation (SMPT) technique. Despite the bulk solids of each component being white in color, the new co-crystal phase exhibited a red color. The new phase was analyzed using single-crystal X-ray diffraction and identified as (APAP) (PDA) (1). Structural analysis revealed PDA to exist in a hitherto unreported zwitterionic form in the co-crystal. A structural analysis of pure PDA revealed the presence of the zwitterion form in (PDA)(H2O) (2), as well. The components of 1 self-assemble as a three-dimensional (3D) hydrogen-bonded network with a pronounced 2D structure. The origin of the red color was investigated using density functional theory calculations, which demonstrate a decreasing π–π* separation involving the components of the solid. © 2010 Wiley-Liss, Inc. and the American Pharmacists Association J Pharm Sci 99:3676–3683, 2010

co-crystals

crystal engineering

crystal structure

crystallization

solid state

Details

Title: Subtitle: A Red Zwitterionic Co-Crystal of Acetaminophen and 2,4-Pyridinedicarboxylic Acid
Creators: John R.G Sander - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242
Dejan-Krešimir Bučar - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242
Rodger F Henry - Structural Chemistry, Global Pharmaceutical R&D, Abbott Laboratories, North Chicago, Illinois 60064
Jonas Baltrusaitis - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242
Geoff G.Z Zhang - Solid State and Material Sciences, Global Pharmaceutical R&D, Abbott Laboratories, North Chicago, Illinois 60064
Leonard R Macgillivray - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242
Resource Type: Journal article
Publication Details: Journal of pharmaceutical sciences, Vol.99(9), pp.3676-3683
DOI: 10.1002/jps.22229
PMID: 20574998
NLM abbreviation: J Pharm Sci
ISSN: 0022-3549
eISSN: 1520-6017
Publisher: Elsevier Inc
Language: English
Date published: 09/2010
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
Record Identifier: 9984216601602771

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