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Title: Melt Crystallization for Paracetamol Polymorphism

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.

Authors:
ORCiD logo [1];  [1]; ORCiD logo [1]; ORCiD logo [1];  [2]; ORCiD logo [1]; ORCiD logo [3]; ORCiD logo [1]; ORCiD logo [1]
  1. New York Univ., New York City, NY (United States)
  2. Argonne National Lab. (ANL), Argonne, IL (United States)
  3. New York Univ., New York City, NY (United States); New York Univ.-East China Normal Univ. Center for Computational Chemistry at NYU Shanghai, Shanghai (China)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); National Science Foundation (NSF)
OSTI Identifier:
1564084
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
Accepted Manuscript
Journal Name:
Crystal Growth and Design
Additional Journal Information:
Journal Volume: 19; Journal Issue: 7; Journal ID: ISSN 1528-7483
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE

Citation Formats

Shtukenberg, Alexander G., Tan, Melissa, Vogt-Maranto, Leslie, Chan, Eric J., Xu, Wenqian, Yang, Jingxiang, Tuckerman, Mark E., Hu, Chunhua T., and Kahr, Bart. Melt Crystallization for Paracetamol Polymorphism. United States: N. p., 2019. Web. doi:10.1021/acs.cgd.9b00473.
Shtukenberg, Alexander G., Tan, Melissa, Vogt-Maranto, Leslie, Chan, Eric J., Xu, Wenqian, Yang, Jingxiang, Tuckerman, Mark E., Hu, Chunhua T., & Kahr, Bart. Melt Crystallization for Paracetamol Polymorphism. United States. doi:10.1021/acs.cgd.9b00473.
Shtukenberg, Alexander G., Tan, Melissa, Vogt-Maranto, Leslie, Chan, Eric J., Xu, Wenqian, Yang, Jingxiang, Tuckerman, Mark E., Hu, Chunhua T., and Kahr, Bart. Mon . "Melt Crystallization for Paracetamol Polymorphism". United States. doi:10.1021/acs.cgd.9b00473.
@article{osti_1564084,
title = {Melt Crystallization for Paracetamol Polymorphism},
author = {Shtukenberg, Alexander G. and Tan, Melissa and Vogt-Maranto, Leslie and Chan, Eric J. and Xu, Wenqian and Yang, Jingxiang and Tuckerman, Mark E. and Hu, Chunhua T. and Kahr, Bart},
abstractNote = {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.},
doi = {10.1021/acs.cgd.9b00473},
journal = {Crystal Growth and Design},
number = 7,
volume = 19,
place = {United States},
year = {2019},
month = {6}
}

Journal Article:
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This content will become publicly available on June 17, 2020
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