The Third Ambient Aspirin Polymorph
Abstract
Polymorphism in aspirin (acetylsalicylic acid), one of the most widely consumed medications, was equivocal until the structure of a second polymorph II, similar in structure to the original form I, was reported in 2005. Here, the third ambient polymorph of aspirin is described. Lastly, it was crystallized from the melt and its structure was determined using a combination of X-ray powder diffraction analysis and crystal structure prediction algorithms.
- Authors:
-
- New York Univ., New York City, NY (United States)
- Univ. of Nevada, Las Vegas, NV (United States)
- Goethe Univ., Frankfurt am Main (Germany)
- Argonne National Lab. (ANL), Argonne, IL (United States)
- New York Univ., New York City, NY (United States); Waseda Univ., Tokyo (Japan)
- Publication Date:
- Research Org.:
- Argonne National Lab. (ANL), Argonne, IL (United States)
- Sponsoring Org.:
- USDOE National Nuclear Security Administration (NNSA); National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22), Scientific User Facilities Division
- OSTI Identifier:
- 1373897
- Grant/Contract Number:
- AC02-06CH11357
- Resource Type:
- Journal Article: Accepted Manuscript
- Journal Name:
- Crystal Growth and Design
- Additional Journal Information:
- Journal Volume: 17; Journal Issue: 6; Journal ID: ISSN 1528-7483
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Shtukenberg, Alexander G., Hu, Chunhua T., Zhu, Qiang, Schmidt, Martin U., Xu, Wenqian, Tan, Melissa, and Kahr, Bart. The Third Ambient Aspirin Polymorph. United States: N. p., 2017.
Web. doi:10.1021/acs.cgd.7b00673.
Shtukenberg, Alexander G., Hu, Chunhua T., Zhu, Qiang, Schmidt, Martin U., Xu, Wenqian, Tan, Melissa, & Kahr, Bart. The Third Ambient Aspirin Polymorph. United States. https://doi.org/10.1021/acs.cgd.7b00673
Shtukenberg, Alexander G., Hu, Chunhua T., Zhu, Qiang, Schmidt, Martin U., Xu, Wenqian, Tan, Melissa, and Kahr, Bart. 2017.
"The Third Ambient Aspirin Polymorph". United States. https://doi.org/10.1021/acs.cgd.7b00673. https://www.osti.gov/servlets/purl/1373897.
@article{osti_1373897,
title = {The Third Ambient Aspirin Polymorph},
author = {Shtukenberg, Alexander G. and Hu, Chunhua T. and Zhu, Qiang and Schmidt, Martin U. and Xu, Wenqian and Tan, Melissa and Kahr, Bart},
abstractNote = {Polymorphism in aspirin (acetylsalicylic acid), one of the most widely consumed medications, was equivocal until the structure of a second polymorph II, similar in structure to the original form I, was reported in 2005. Here, the third ambient polymorph of aspirin is described. Lastly, it was crystallized from the melt and its structure was determined using a combination of X-ray powder diffraction analysis and crystal structure prediction algorithms.},
doi = {10.1021/acs.cgd.7b00673},
url = {https://www.osti.gov/biblio/1373897},
journal = {Crystal Growth and Design},
issn = {1528-7483},
number = 6,
volume = 17,
place = {United States},
year = {Wed May 17 00:00:00 EDT 2017},
month = {Wed May 17 00:00:00 EDT 2017}
}
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Cited by: 59 works
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Figures / Tables:
Figure 1: Polarized light optical micrograph showing simultaneous crystallization of banded spherulites of aspirin I and or II characterized by concentric optical rings, and smooth spherulites of aspirin IV from the melt containing 16.6 wt.% Canada balsam at room temperature.
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Works referenced in this record:
Aspirin: Dissolution Rates of Two Polymorphic Forms
journal, April 1968
- Tawashi, R.
- Science, Vol. 160, Issue 3823
The Predictably Elusive Form II of Aspirin
journal, December 2005
- Vishweshwar, Peddy; McMahon, Jennifer A.; Oliveira, Mark
- Journal of the American Chemical Society, Vol. 127, Issue 48
Toward Crystal Structure Prediction for Conformationally Flexible Molecules: The Headaches Illustrated by Aspirin
journal, November 2004
- Ouvrard, Carole; Price, Sarah L.
- Crystal Growth & Design, Vol. 4, Issue 6
On the Polymorphism of Aspirin: Crystalline Aspirin as Intergrowths of Two “Polymorphic” Domains
journal, January 2007
- Bond, Andrew D.; Boese, Roland; Desiraju, Gautam R.
- Angewandte Chemie International Edition, Vol. 46, Issue 4
On the Polymorphism of Aspirin
journal, January 2007
- Bond, Andrew D.; Boese, Roland; Desiraju, Gautam R.
- Angewandte Chemie International Edition, Vol. 46, Issue 4
Single crystals of aspirin form II: crystallisation and stability
journal, January 2011
- Bond, Andrew D.; Solanko, Katarzyna A.; Parsons, Simon
- CrystEngComm, Vol. 13, Issue 2
High-pressure polymorphism of acetylsalicylic acid (aspirin): Raman spectroscopy
journal, February 2015
- Crowell, Ethan L.; Dreger, Zbigniew A.; Gupta, Yogendra M.
- Journal of Molecular Structure, Vol. 1082
Growth Actuated Bending and Twisting of Single Crystals
journal, January 2014
- Shtukenberg, Alexander G.; Punin, Yurii O.; Gujral, Ankit
- Angewandte Chemie International Edition, Vol. 53, Issue 3
Circular Birefringence of Banded Spherulites
journal, February 2014
- Cui, Xiaoyan; Shtukenberg, Alexander G.; Freudenthal, John
- Journal of the American Chemical Society, Vol. 136, Issue 14
Twisted Aspirin Crystals
journal, February 2013
- Cui, Xiaoyan; Rohl, Andrew L.; Shtukenberg, Alexander
- Journal of the American Chemical Society, Vol. 135, Issue 9
Spherulites
journal, November 2011
- Shtukenberg, Alexander G.; Punin, Yuri O.; Gunn, Erica
- Chemical Reviews, Vol. 112, Issue 3
Monte Carlo indexing with McMaille
journal, September 2004
- Le Bail, A.
- Powder Diffraction, Vol. 19, Issue 3
Indexing of powder diffraction patterns for low-symmetry lattices by the successive dichotomy method
journal, December 1991
- Boultif, A.; Louër, D.
- Journal of Applied Crystallography, Vol. 24, Issue 6
Constrained evolutionary algorithm for structure prediction of molecular crystals: methodology and applications
journal, May 2012
- Zhu, Qiang; Oganov, Artem R.; Glass, Colin W.
- Acta Crystallographica Section B Structural Science, Vol. 68, Issue 3
New developments in evolutionary structure prediction algorithm USPEX
journal, April 2013
- Lyakhov, Andriy O.; Oganov, Artem R.; Stokes, Harold T.
- Computer Physics Communications, Vol. 184, Issue 4
The Structure of Glycine Dihydrate: Implications for the Crystallization of Glycine from Solution and Its Structure in Outer Space
journal, January 2017
- Xu, Wenqian; Zhu, Qiang; Hu, Chunhua Tony
- Angewandte Chemie International Edition, Vol. 56, Issue 8
CHARMM: A program for macromolecular energy, minimization, and dynamics calculations
journal, July 1983
- Brooks, Bernard R.; Bruccoleri, Robert E.; Olafson, Barry D.
- Journal of Computational Chemistry, Vol. 4, Issue 2
Extension of the CHARMM general force field to sulfonyl-containing compounds and its utility in biomolecular simulations
journal, July 2012
- Yu, Wenbo; He, Xibing; Vanommeslaeghe, Kenno
- Journal of Computational Chemistry, Vol. 33, Issue 31
DFTB+, a Sparse Matrix-Based Implementation of the DFTB Method †
journal, July 2007
- Aradi, B.; Hourahine, B.; Frauenheim, Th.
- The Journal of Physical Chemistry A, Vol. 111, Issue 26
Parametrization and Benchmark of DFTB3 for Organic Molecules
journal, November 2012
- Gaus, Michael; Goez, Albrecht; Elstner, Marcus
- Journal of Chemical Theory and Computation, Vol. 9, Issue 1
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set
journal, October 1996
- Kresse, G.; Furthmüller, J.
- Physical Review B, Vol. 54, Issue 16, p. 11169-11186
Van der Waals density functionals applied to solids
journal, May 2011
- Klimeš, Jiří; Bowler, David R.; Michaelides, Angelos
- Physical Review B, Vol. 83, Issue 19
Unit-cell refinement from powder diffraction scans
journal, December 1981
- Pawley, G. S.
- Journal of Applied Crystallography, Vol. 14, Issue 6
COMPACK : a program for identifying crystal structure similarity using distances
journal, January 2005
- Chisholm, James Alexander; Motherwell, Sam
- Journal of Applied Crystallography, Vol. 38, Issue 1
Evaluation of Shear-Slip Transitions in Crystalline Aspirin by Density-Functional Theory
journal, October 2016
- LeBlanc, Luc M.; Otero-de-la-Roza, Alberto; Johnson, Erin R.
- Crystal Growth & Design, Vol. 16, Issue 12
Role of Dispersion Interactions in the Polymorphism and Entropic Stabilization of the Aspirin Crystal
journal, July 2014
- Reilly, Anthony M.; Tkatchenko, Alexandre
- Physical Review Letters, Vol. 113, Issue 5
Resorcinol Crystallization from the Melt: A New Ambient Phase and New “Riddles”
journal, March 2016
- Zhu, Qiang; Shtukenberg, Alexander G.; Carter, Damien J.
- Journal of the American Chemical Society, Vol. 138, Issue 14
Works referencing / citing this record:
Discovery of new polymorphs of the tuberculosis drug isoniazid
journal, January 2020
- Zhang, Keke; Fellah, Noalle; Shtukenberg, Alexander G.
- CrystEngComm
Evolutionary niching in the GAtor genetic algorithm for molecular crystal structure prediction
journal, January 2018
- Curtis, Farren; Rose, Timothy; Marom, Noa
- Faraday Discussions, Vol. 211
Control and prediction of the organic solid state: a challenge to theory and experiment
journal, September 2018
- Price, Sarah L.
- Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 474, Issue 2217
Structure prediction drives materials discovery
journal, April 2019
- Oganov, Artem R.; Pickard, Chris J.; Zhu, Qiang
- Nature Reviews Materials, Vol. 4, Issue 5
Probing stress induced phase transformation in aspirin polymorphs using Raman spectroscopy enabled nanoindentation
journal, January 2019
- Manimunda, Praveena; Syed Asif, S. A.; Mishra, Manish Kumar
- Chemical Communications, Vol. 55, Issue 62
Confinement-induced polymorphism in acetylsalicylic acid–nanoporous glass composites
journal, August 2018
- Peksa, P.; Trzmiel, J.; Ptak, M.
- Journal of Materials Science, Vol. 54, Issue 1
ROY revisited, again: the eighth solved structure
journal, January 2018
- Tan, Melissa; Shtukenberg, Alexander G.; Zhu, Shengcai
- Faraday Discussions, Vol. 211
Polymorphism of griseofulvin: concomitant crystallization from the melt and a single crystal structure of a metastable polymorph with anomalously large thermal expansion
journal, January 2018
- Su, Yuan; Xu, Jia; Shi, Qin
- Chemical Communications, Vol. 54, Issue 4
Structure Prediction Drives Materials Discovery
text, January 2019
- Oganov, Artem; Pickard, Christopher; Zhu, Qiang
- Apollo - University of Cambridge Repository
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