Melt Crystallization for Paracetamol Polymorphism

Alexander G. Shtukenberg, Melissa Tan, Leslie Vogt-Maranto, Eric J. Chan, Wenqian Xu, Jingxiang Yang, Mark Tuckerman, Chunhua T. Hu, Bart Kahr

Research output: Contribution to journalArticle

Abstract

Trimorphic paracetamol, one of the most commonly used analgesic and antipyretic drugs, has been a model system for studying transformations among phases of molecular crystalline materials. During crystallization from the melt and the glass above 0 °C, three new polymorphs of paracetamol (N-acetyl-para-aminophenol or acetaminophen) were discovered, doubling the number of known ambient forms. The crystal structure of one new form was solved using a combination of powder X-ray diffraction and computational techniques. Growth kinetics became anomalous near the glass transition: as temperature decreased, growth rate increased; this rare and poorly understood phenomenon is commonly identified as the glass-to-crystal (GC) growth mode. In addition, two polymorphs displayed optical evidence of helicoidal morphologies, a characteristic of at least 25% of molecular crystals, that has been resistant to a universal explanation.

Original languageEnglish (US)
JournalCrystal Growth and Design
DOIs
StatePublished - Jan 1 2019

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polymorphism
Acetaminophen
Crystallization
Polymorphism
crystallization
Molecular crystals
Glass
glass
Growth kinetics
Crystal growth
X ray powder diffraction
Glass transition
Antipyretics
Crystal structure
Crystalline materials
phase transformations
Analgesics
crystal growth
drugs
crystal structure

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

Shtukenberg, A. G., Tan, M., Vogt-Maranto, L., Chan, E. J., Xu, W., Yang, J., ... Kahr, B. (2019). Melt Crystallization for Paracetamol Polymorphism. Crystal Growth and Design. https://doi.org/10.1021/acs.cgd.9b00473

Melt Crystallization for Paracetamol Polymorphism. / Shtukenberg, Alexander G.; Tan, Melissa; Vogt-Maranto, Leslie; Chan, Eric J.; Xu, Wenqian; Yang, Jingxiang; Tuckerman, Mark; Hu, Chunhua T.; Kahr, Bart.

In: Crystal Growth and Design, 01.01.2019.

Research output: Contribution to journalArticle

Shtukenberg AG, Tan M, Vogt-Maranto L, Chan EJ, Xu W, Yang J et al. Melt Crystallization for Paracetamol Polymorphism. Crystal Growth and Design. 2019 Jan 1. https://doi.org/10.1021/acs.cgd.9b00473
Shtukenberg, Alexander G. ; Tan, Melissa ; Vogt-Maranto, Leslie ; Chan, Eric J. ; Xu, Wenqian ; Yang, Jingxiang ; Tuckerman, Mark ; Hu, Chunhua T. ; Kahr, Bart. / Melt Crystallization for Paracetamol Polymorphism. In: Crystal Growth and Design. 2019.
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