Melt Crystallization for Paracetamol Polymorphism

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

doi:10.1021/acs.cgd.9b00473

Title: Melt Crystallization for Paracetamol Polymorphism

Journal Article · 17 June 2019 · Crystal Growth and Design

DOI: https://doi.org/10.1021/acs.cgd.9b00473 · OSTI ID:1564084

^[1]; Tan, Melissa ^[1];

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New York Univ., New York City, NY (United States)
Argonne National Lab. (ANL), Argonne, IL (United States)
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)

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.

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Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); National Science Foundation (NSF)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1564084

Journal Information:: Crystal Growth and Design, Journal Name: Crystal Growth and Design Journal Issue: 7 Vol. 19; ISSN 1528-7483

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (56)

Upack program package for crystal structure prediction: Force fields and crystal structure generation for small carbohydrate molecules van Eijck, Bouke P.; Kroon, Jan Journal of Computational Chemistry, Vol. 20, Issue 8 https://doi.org/10.1002/(SICI)1096-987X(199906)20:8<799::AID-JCC6>3.0.CO;2-Z	journal	June 1999
DDT Polymorphism and the Lethality of Crystal Forms Yang, Jingxiang; Hu, C. T.; Zhu, Xiaolong Angewandte Chemie, Vol. 129, Issue 34 https://doi.org/10.1002/ange.201703028	journal	June 2017
Growth Actuated Bending and Twisting of Single Crystals Shtukenberg, Alexander G.; Punin, Yurii O.; Gujral, Ankit Angewandte Chemie International Edition, Vol. 53, Issue 3 https://doi.org/10.1002/anie.201301223	journal	January 2014
Bernauer′s Bands Shtukenberg, Alexander; Gunn, Erica; Gazzano, Massimo ChemPhysChem, Vol. 12, Issue 8 https://doi.org/10.1002/cphc.201000963	journal	March 2011
Development and testing of a general amber force field Wang, Junmei; Wolf, Romain M.; Caldwell, James W. Journal of Computational Chemistry, Vol. 25, Issue 9 https://doi.org/10.1002/jcc.20035	journal	January 2004
Effect of the damping function in dispersion corrected density functional theory Grimme, Stefan; Ehrlich, Stephan; Goerigk, Lars Journal of Computational Chemistry, Vol. 32, Issue 7 https://doi.org/10.1002/jcc.21759	journal	March 2011
Determination of Phenylpropanolamine Hydrochloride and Acetaminophen in Pharmaceutical Preparations by Raman Spectroscopy King, Thomas H.; Mann, Charles K.; Vickers, Thomas J. Journal of Pharmaceutical Sciences, Vol. 74, Issue 4 https://doi.org/10.1002/jps.2600740415	journal	April 1985
cp2k: atomistic simulations of condensed matter systems Hutter, Jürg; Iannuzzi, Marcella; Schiffmann, Florian Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 4, Issue 1 https://doi.org/10.1002/wcms.1159	journal	June 2013
Preparation and physical characterization of forms II and III of paracetamol Di Martino, P.; Conflant, P.; Drache, M. Journal of thermal analysis, Vol. 48, Issue 3 https://doi.org/10.1007/BF01979491	journal	March 1997
Pseudopotentials for H to Kr optimized for gradient-corrected exchange-correlation functionals Krack, M. Theoretical Chemistry Accounts, Vol. 114, Issue 1-3 https://doi.org/10.1007/s00214-005-0655-y	journal	May 2005
Quickstep: Fast and accurate density functional calculations using a mixed Gaussian and plane waves approach VandeVondele, Joost; Krack, Matthias; Mohamed, Fawzi Computer Physics Communications, Vol. 167, Issue 2 https://doi.org/10.1016/j.cpc.2004.12.014	journal	April 2005
An investigation into the effects of thermal history on the crystallisation behaviour of amorphous paracetamol Qi, Sheng; Avalle, Paolo; Saklatvala, Robert European Journal of Pharmaceutics and Biopharmaceutics, Vol. 69, Issue 1 https://doi.org/10.1016/j.ejpb.2007.10.008	journal	May 2008
Enforcing Ostwald's rule of stages: Isolation of paracetamol forms III and II Burley, Jonathan C.; Duer, Melinda J.; Stein, Robin S. European Journal of Pharmaceutical Sciences, Vol. 31, Issue 5 https://doi.org/10.1016/j.ejps.2007.04.002	journal	August 2007
The interplay between the paracetamol polymorphism and its molecular structures dissolved in supercritical CO2 in contact with the solid phase: In situ vibration spectroscopy and molecular dynamics simulation analysis Oparin, Roman D.; Moreau, Myriam; De Walle, Isabelle European Journal of Pharmaceutical Sciences, Vol. 77 https://doi.org/10.1016/j.ejps.2015.05.016	journal	September 2015
Raman detected differential scanning calorimetry of polymorphic transformations in acetaminophen Kauffman, John F.; Batykefer, Linda M.; Tuschel, David D. Journal of Pharmaceutical and Biomedical Analysis, Vol. 48, Issue 5 https://doi.org/10.1016/j.jpba.2008.09.008	journal	December 2008
Conformational and vibrational reassessment of solid paracetamol Amado, Ana M.; Azevedo, Celeste; Ribeiro-Claro, Paulo J. A. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 183 https://doi.org/10.1016/j.saa.2017.04.076	journal	August 2017
Multichannel Mueller matrix ellipsometer based on the dual rotating compensator principle Chen, Chi; An, Ilsin; Ferreira, G. M. Thin Solid Films, Vol. 455-456 https://doi.org/10.1016/j.tsf.2003.11.191	journal	May 2004
The Third Ambient Aspirin Polymorph Shtukenberg, Alexander G.; Hu, Chunhua T.; Zhu, Qiang Crystal Growth & Design, Vol. 17, Issue 6 https://doi.org/10.1021/acs.cgd.7b00673	journal	May 2017
Nucleation of Molecular Crystals Driven by Relative Information Entropy Gobbo, Gianpaolo; Bellucci, Michael A.; Tribello, Gareth A. Journal of Chemical Theory and Computation, Vol. 14, Issue 2 https://doi.org/10.1021/acs.jctc.7b01027	journal	January 2018
Fast Crystal Growth in o -Terphenyl Glasses: A Possible Role for Fracture and Surface Mobility Powell, C. Travis; Xi, Hanmi; Sun, Ye The Journal of Physical Chemistry B, Vol. 119, Issue 31 https://doi.org/10.1021/acs.jpcb.5b05389	journal	July 2015
Bulk and Surface-Stabilized Structures of Paracetamol Revisited by Raman Confocal Microscopy Rivalta, Arianna; Salzillo, Tommaso; Venuti, Elisabetta ACS Omega, Vol. 3, Issue 8 https://doi.org/10.1021/acsomega.8b01246	journal	August 2018
Glass-Crystal Growth Mode for Testosterone Propionate Shtukenberg, Alexander; Freundenthal, John; Gunn, Erica Crystal Growth & Design, Vol. 11, Issue 10 https://doi.org/10.1021/cg200640g	journal	October 2011
Spherulites Shtukenberg, Alexander G.; Punin, Yuri O.; Gunn, Erica Chemical Reviews, Vol. 112, Issue 3 https://doi.org/10.1021/cr200297f	journal	November 2011
A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model Bayly, Christopher I.; Cieplak, Piotr; Cornell, Wendy The Journal of Physical Chemistry, Vol. 97, Issue 40 https://doi.org/10.1021/j100142a004	journal	October 1993
Reversible Twisting during Helical Hippuric Acid Crystal Growth Shtukenberg, Alexander G.; Freudenthal, John; Kahr, Bart Journal of the American Chemical Society, Vol. 132, Issue 27 https://doi.org/10.1021/ja101491n	journal	July 2010
Resorcinol Crystallization from the Melt: A New Ambient Phase and New “Riddles” Zhu, Qiang; Shtukenberg, Alexander G.; Carter, Damien J. Journal of the American Chemical Society, Vol. 138, Issue 14 https://doi.org/10.1021/jacs.6b01120	journal	March 2016
Dichroism in Helicoidal Crystals Cui, Xiaoyan; Nichols, Shane M.; Arteaga, Oriol Journal of the American Chemical Society, Vol. 138, Issue 37 https://doi.org/10.1021/jacs.6b06278	journal	September 2016
Polymorphism in Paracetamol: Evidence of Additional Forms IV and V at High Pressure Smith, Spencer J.; Bishop, Matthew M.; Montgomery, Jeffrey M. The Journal of Physical Chemistry A, Vol. 118, Issue 31 https://doi.org/10.1021/jp411810y	journal	July 2014
Crystallization near Glass Transition: Transition from Diffusion-Controlled to Diffusionless Crystal Growth Studied with Seven Polymorphs Sun, Ye; Xi, Hanmi; Chen, Shuang The Journal of Physical Chemistry B, Vol. 112, Issue 18 https://doi.org/10.1021/jp7120577	journal	May 2008
Termination of Solid-State Crystal Growth in Molecular Glasses by Fluidity Musumeci, Daniele; Powell, C. Travis; Ediger, M. D. The Journal of Physical Chemistry Letters, Vol. 5, Issue 10 https://doi.org/10.1021/jz5006169	journal	May 2014
Investigating the Recrystallization Behavior of Amorphous Paracetamol by Variable Temperature Raman Studies and Surface Raman Mapping Nanubolu, Jagadeesh Babu; Burley, Jonathan C. Molecular Pharmaceutics, Vol. 9, Issue 6 https://doi.org/10.1021/mp300035g	journal	May 2012
Crystallization and Phase Changes in Paracetamol from the Amorphous Solid to the Liquid Phase Sibik, Juraj; Sargent, Michael J.; Franklin, Miriam Molecular Pharmaceutics, Vol. 11, Issue 4 https://doi.org/10.1021/mp400768m	journal	March 2014
DSC and adiabatic calorimetry study of the polymorphs of paracetamol Boldyreva, Elena V.; Drebushchak, V. A.; Paukov, I. E. Journal of Thermal Analysis and Calorimetry, Vol. 77, Issue 2 https://doi.org/10.1023/B:JTAN.0000038998.47606.27	journal	January 2004
Mechanics of twisted hippuric acid crystals untwisting as they grow Shtukenberg, Alexander G.; Gujral, Ankit; Rosseeva, Elena CrystEngComm, Vol. 17, Issue 46 https://doi.org/10.1039/C5CE00195A	journal	January 2015
Powder diffraction and crystal structure prediction identify four new coumarin polymorphs Shtukenberg, Alexander G.; Zhu, Qiang; Carter, Damien J. Chemical Science, Vol. 8, Issue 7 https://doi.org/10.1039/C7SC00168A	journal	January 2017
ROY revisited, again: the eighth solved structure Tan, Melissa; Shtukenberg, Alexander G.; Zhu, Shengcai Faraday Discussions, Vol. 211 https://doi.org/10.1039/C8FD00039E	journal	January 2018
The errors in lattice energy minimisation studies: sensitivity to experimental variations in the molecular structure of paracetamol Beyer, Theresa; L. Price, Sarah CrystEngComm, Vol. 2, Issue 34 https://doi.org/10.1039/b006604o	journal	January 2000
Crystal structure determination of the elusive paracetamol Form III Perrin, Marc-Antoine; Neumann, Marcus A.; Elmaleh, Hagit Chemical Communications, Issue 22 https://doi.org/10.1039/b822882e	journal	January 2009
Can crystal structure prediction guide experimentalists to a new polymorph of paracetamol? Neumann, Marcus Aurelius; Perrin, Marc-Antoine CrystEngComm, Vol. 11, Issue 11 https://doi.org/10.1039/b909819d	journal	January 2009
Dynamics of the intermolecular hydrogen bonds in the polymorphs of paracetamol in relation to crystal packing and conformational transitions: a variable-temperature polarized Raman spectroscopy study Kolesov, Boris A.; Mikhailenko, Mikhail A.; Boldyreva, Elena V. Physical Chemistry Chemical Physics, Vol. 13, Issue 31 https://doi.org/10.1039/c1cp20139e	journal	January 2011
Size-dependent growth of polymorphs in nanopores and Ostwald's step rule of stages Rengarajan, G. T.; Enke, D.; Steinhart, M. Physical Chemistry Chemical Physics, Vol. 13, Issue 48 https://doi.org/10.1039/c1cp22679g	journal	January 2011
Glass Transition in o ‐Terphenyl Greet, R. J.; Turnbull, D. The Journal of Chemical Physics, Vol. 46, Issue 4 https://doi.org/10.1063/1.1840842	journal	February 1967
Diffusion-controlled and diffusionless crystal growth in liquid o-terphenyl near its glass transition temperature Xi, Hanmi; Sun, Ye; Yu, Lian The Journal of Chemical Physics, Vol. 130, Issue 9 https://doi.org/10.1063/1.3081047	journal	March 2009
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
A hybrid Gaussian and plane wave density functional scheme Lippert, Gerald; Hutter, JuRG; Parrinello, Michele Molecular Physics, Vol. 92, Issue 3 https://doi.org/10.1080/00268979709482119	journal	October 1997
Separable dual-space Gaussian pseudopotentials Goedecker, S.; Teter, M.; Hutter, J. Physical Review B, Vol. 54, Issue 3 https://doi.org/10.1103/PhysRevB.54.1703	journal	July 1996
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
COMPACK : a program for identifying crystal structure similarity using distances Chisholm, James Alexander; Motherwell, Sam Journal of Applied Crystallography, Vol. 38, Issue 1 https://doi.org/10.1107/S0021889804027074	journal	January 2005
The orthorhombic form of p-hydroxyacetanilide Haisa, M.; Kashino, S.; Maeda, H. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 30, Issue 10 https://doi.org/10.1107/S0567740874007473	journal	October 1974
The Monoclinic Form of p-Hydroxyacetanilide Haisa, M.; Kashino, S.; Kawai, R. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 32, Issue 4 https://doi.org/10.1107/S0567740876012223	journal	April 1976
Reassessment of paracetamol orthorhombic Form III and determination of a novel low-temperature monoclinic Form III-m from powder diffraction data Reiss, Céleste A.; Mechelen, Jan B. van; Goubitz, Kees Acta Crystallographica Section C Structural Chemistry, Vol. 74, Issue 3 https://doi.org/10.1107/S2053229618002619	journal	February 2018
Monte Carlo indexing with McMaille Le Bail, A. Powder Diffraction, Vol. 19, Issue 3 https://doi.org/10.1154/1.1763152	journal	September 2004
Transformation of Metastable Forms of Acetaminophen Studied by Thermal Fourier Transform Infrared (FT-IR) Microspectroscopy. Wang, Shun-Li; Lin, Shan-Yang; Wei, Yen-Shan Chemical and Pharmaceutical Bulletin, Vol. 50, Issue 2 https://doi.org/10.1248/cpb.50.153	journal	January 2002
Mueller matrix microscope with a dual continuous rotating compensator setup and digital demodulation Arteaga, Oriol; Baldrís, Marta; Antó, Joan Applied Optics, Vol. 53, Issue 10 https://doi.org/10.1364/AO.53.002236	journal	January 2014
Characterization of Acetaminophen: Molecular Microanalysis with Raman Microprobe Spectroscopy Pestaner, Joseph P.; Mullick, Florabel G.; Centeno, Jose A. Journal of Forensic Sciences, Vol. 41, Issue 6 https://doi.org/10.1520/JFS14050J	journal	November 1996
A Study of the Changes During Heating of Paracetamol de Wet, F. N.; Gerber, J. J.; Lotter, A. P. Drug Development and Industrial Pharmacy, Vol. 24, Issue 5 https://doi.org/10.3109/03639049809085642	journal	January 1998

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