ζ-Glycine: insight into the mechanism of a polymorphic phase transition
Abstract
Glycine is the simplest and most polymorphic amino acid, with five phases having been structurally characterized at atmospheric or high pressure. A sixth form, the elusive ζ phase, was discovered over a decade ago as a short-lived intermediate which formed as the high-pressure ϵ phase transformed to the γ form on decompression. However, its structure has remained unsolved. We now report the structure of the ζ phase, which was trapped at 100 K enabling neutron powder diffraction data to be obtained. The structure was solved using the results of a crystal structure prediction procedure based on fullyab initioenergy calculations combined with a genetic algorithm for searching phase space. We show that the fate of ζ-glycine depends on its thermal history: although at room temperature it transforms back to the γ phase, warming the sample from 100 K to room temperature yielded β-glycine, the least stable of the known ambient-pressure polymorphs.
- Authors:
-
[1];
[3];
[3];
[4];
[6]
- Harwell Science and Innovation Camus, Didcot (United Kingdom). Rutherford-Appleton Lab. ISIS Facility
- Harwell Science and Innovation Camus, Didcot (United Kingdom). Rutherford-Appleton Lab. ISIS Facility; Univ. of Edinburgh, Scotland (United Kingdom). School of Chemistry and Centre for Science at Extreme Conditions
- Scuola Internazionale Superiore di Studi Avanzati, Trieste (Italy)
- Univ. of Edinburgh, Scotland (United Kingdom). School of Chemistry and Centre for Science at Extreme Conditions
- Scuola Internazionale Superiore di Studi Avanzati, Trieste (Italy); Univ. of California, San Diego, CA (United States). Dept. of Chemistry and Biochemistry
- Harwell Science and Innovation Camus, Didcot (United Kingdom). Rutherford-Appleton Lab. ISIS Facility; Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Publication Date:
- Research Org.:
- Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC)
- OSTI Identifier:
- 1625820
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Accepted Manuscript
- Journal Name:
- IUCrJ
- Additional Journal Information:
- Journal Volume: 4; Journal Issue: 5; Journal ID: ISSN 2052-2525
- Publisher:
- International Union of Crystallography
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; Chemistry; Crystallography; Materials Science
Citation Formats
Bull, Craig L., Flowitt-Hill, Giles, de Gironcoli, Stefano, Küçükbenli, Emine, Parsons, Simon, Pham, Cong Huy, Playford, Helen Y., and Tucker, Matthew G. ζ-Glycine: insight into the mechanism of a polymorphic phase transition. United States: N. p., 2017.
Web. doi:10.1107/s205225251701096x.
Bull, Craig L., Flowitt-Hill, Giles, de Gironcoli, Stefano, Küçükbenli, Emine, Parsons, Simon, Pham, Cong Huy, Playford, Helen Y., & Tucker, Matthew G. ζ-Glycine: insight into the mechanism of a polymorphic phase transition. United States. https://doi.org/10.1107/s205225251701096x
Bull, Craig L., Flowitt-Hill, Giles, de Gironcoli, Stefano, Küçükbenli, Emine, Parsons, Simon, Pham, Cong Huy, Playford, Helen Y., and Tucker, Matthew G. Fri .
"ζ-Glycine: insight into the mechanism of a polymorphic phase transition". United States. https://doi.org/10.1107/s205225251701096x. https://www.osti.gov/servlets/purl/1625820.
@article{osti_1625820,
title = {ζ-Glycine: insight into the mechanism of a polymorphic phase transition},
author = {Bull, Craig L. and Flowitt-Hill, Giles and de Gironcoli, Stefano and Küçükbenli, Emine and Parsons, Simon and Pham, Cong Huy and Playford, Helen Y. and Tucker, Matthew G.},
abstractNote = {Glycine is the simplest and most polymorphic amino acid, with five phases having been structurally characterized at atmospheric or high pressure. A sixth form, the elusive ζ phase, was discovered over a decade ago as a short-lived intermediate which formed as the high-pressure ϵ phase transformed to the γ form on decompression. However, its structure has remained unsolved. We now report the structure of the ζ phase, which was trapped at 100 K enabling neutron powder diffraction data to be obtained. The structure was solved using the results of a crystal structure prediction procedure based on fullyab initioenergy calculations combined with a genetic algorithm for searching phase space. We show that the fate of ζ-glycine depends on its thermal history: although at room temperature it transforms back to the γ phase, warming the sample from 100 K to room temperature yielded β-glycine, the least stable of the known ambient-pressure polymorphs.},
doi = {10.1107/s205225251701096x},
journal = {IUCrJ},
number = 5,
volume = 4,
place = {United States},
year = {Fri Sep 01 00:00:00 EDT 2017},
month = {Fri Sep 01 00:00:00 EDT 2017}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Raman observation of a new (ζ) polymorph of glycine?
journal, February 2006
- Goryainov, S. V.; Boldyreva, E. V.; Kolesnik, E. N.
- Chemical Physics Letters, Vol. 419, Issue 4-6
Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures
journal, March 2008
- Macrae, Clare F.; Bruno, Ian J.; Chisholm, James A.
- Journal of Applied Crystallography, Vol. 41, Issue 2
How to quantify energy landscapes of solids
journal, March 2009
- Oganov, Artem R.; Valle, Mario
- The Journal of Chemical Physics, Vol. 130, Issue 10
Structure−Property Relationships in the Crystals of the Smallest Amino Acid: An Incoherent Inelastic Neutron Scattering Study of the Glycine Polymorphs
journal, July 2008
- Bordallo, Heloisa N.; Boldyreva, Elena V.; Buchsteiner, Alexandra
- The Journal of Physical Chemistry B, Vol. 112, Issue 29
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, Vol. 129, Issue 8
Crystal structure prediction from first principles
journal, December 2008
- Woodley, Scott M.; Catlow, Richard
- Nature Materials, Vol. 7, Issue 12
Structural evolution of amino acid crystals under stress from a non-empirical density functional
journal, October 2012
- Sabatini, Riccardo; Küçükbenli, Emine; Kolb, Brian
- Journal of Physics: Condensed Matter, Vol. 24, Issue 42
Wavefunction methods for noncovalent interactions: Noncovalent interactions
journal, July 2011
- Hohenstein, Edward G.; Sherrill, C. David
- Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 2
Efficient computer modeling of organic materials. The atom–atom, Coulomb–London–Pauli (AA-CLP) model for intermolecular electrostatic-polarization, dispersion and repulsion energies
journal, January 2011
- Gavezzotti, Angelo
- New Journal of Chemistry, Vol. 35, Issue 7
How focussing on hydrogen bonding interactions in amino acids can miss the bigger picture: a high-pressure neutron powder diffraction study of ε-glycine
journal, January 2015
- Moggach, Stephen A.; Marshall, William G.; Rogers, David M.
- CrystEngComm, Vol. 17, Issue 28
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
Nonphotochemical, Laser-Induced Nucleation of Supersaturated Aqueous Glycine Produces Unexpected γ-Polymorph
journal, January 2001
- Zaccaro, Julien; Matic, Jelena; Myerson, Allan S.
- Crystal Growth & Design, Vol. 1, Issue 1
An experimental study of the influence of temperature on a hydrogen-bonded system: the crystal structure of γ-glycine at 83 K and 298 K by neutron diffraction
journal, January 1980
- Kvick, Å ;.; Canning, W. M.; Koetzle, T. F.
- Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 36, Issue 1
QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials
journal, September 2009
- Giannozzi, Paolo; Baroni, Stefano; Bonini, Nicola
- Journal of Physics: Condensed Matter, Vol. 21, Issue 39, Article No. 395502
An investigation into the effects of thermal history on the crystallisation behaviour of amorphous paracetamol
journal, May 2008
- Qi, Sheng; Avalle, Paolo; Saklatvala, Robert
- European Journal of Pharmaceutics and Biopharmaceutics, Vol. 69, Issue 1
The high-pressure phase diagram of ammonia dihydrate
journal, June 2007
- Fortes, A. D.; Wood, I. G.; Alfredsson, M.
- High Pressure Research, Vol. 27, Issue 2
An ab Initio Study of Observed and Hypothetical Polymorphs of Glycine
journal, July 2005
- Chisholm, James A.; Motherwell, Sam; Tulip, Paul R.
- Crystal Growth & Design, Vol. 5, Issue 4
PEARL: the high pressure neutron powder diffractometer at ISIS
journal, August 2016
- Bull, C. L.; Funnell, N. P.; Tucker, M. G.
- High Pressure Research, Vol. 36, Issue 4
Efficient evaluation of triple excitations in symmetry-adapted perturbation theory via second-order Møller–Plesset perturbation theory natural orbitals
journal, September 2010
- Hohenstein, Edward G.; Sherrill, C. David
- The Journal of Chemical Physics, Vol. 133, Issue 10
Inhomogeneous Electron Gas
journal, November 1964
- Hohenberg, P.; Kohn, W.
- Physical Review, Vol. 136, Issue 3B, p. B864-B871
Density fitting of intramonomer correlation effects in symmetry-adapted perturbation theory
journal, July 2010
- Hohenstein, Edward G.; Sherrill, C. David
- The Journal of Chemical Physics, Vol. 133, Issue 1
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
Solid form and solubility
journal, January 2017
- Hunter, Christopher A.; Prohens, Rafel
- CrystEngComm, Vol. 19, Issue 1
Solid-state characterization of paracetamol metastable polymorphs formed in binary mixtures with hydroxypropylmethylcellulose
journal, November 2003
- Rossi, Alessandra; Savioli, Alessandra; Bini, Marcella
- Thermochimica Acta, Vol. 406, Issue 1-2
Effect of High Pressure on the Crystal Structures of Polymorphs of Glycine
journal, July 2005
- Dawson, Alice; Allan, David R.; Belmonte, Scott A.
- Crystal Growth & Design, Vol. 5, Issue 4
A reversible pressure-induced phase transition in β-glycine at 0.76GPa
journal, March 2005
- Goryainov, S. V.; Kolesnik, E. N.; Boldyreva, E. V.
- Physica B: Condensed Matter, Vol. 357, Issue 3-4
Crystal structure prediction from first principles: The crystal structures of glycine
journal, April 2015
- Lund, Albert M.; Pagola, Gabriel I.; Orendt, Anita M.
- Chemical Physics Letters, Vol. 626
Single-crystal structure validation with the program PLATON
journal, January 2003
- Spek, A. L.
- Journal of Applied Crystallography, Vol. 36, Issue 1, p. 7-13
Report on the sixth blind test of organic crystal structure prediction methods
journal, August 2016
- Reilly, Anthony M.; Cooper, Richard I.; Adjiman, Claire S.
- Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 4
α-Glycine under high pressures: a Raman scattering study
journal, November 2003
- Murli, Chitra; Sharma, Surinder M.; Karmakar, S.
- Physica B: Condensed Matter, Vol. 339, Issue 1
Psi4: an open-source ab initio electronic structure program : Psi4: an electronic structure program
journal, October 2011
- Turney, Justin M.; Simmonett, Andrew C.; Parrish, Robert M.
- Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 4
Many-Body Dispersion Interactions in Molecular Crystal Polymorphism
journal, May 2013
- Marom, Noa; DiStasio, Robert A.; Atalla, Viktor
- Angewandte Chemie International Edition, Vol. 52, Issue 26
Perturbation Theory Approach to Intermolecular Potential Energy Surfaces of van der Waals Complexes
journal, November 1994
- Jeziorski, Bogumil; Moszynski, Robert; Szalewicz, Krzysztof
- Chemical Reviews, Vol. 94, Issue 7
van der Waals forces in density functional theory: a review of the vdW-DF method
journal, May 2015
- Berland, Kristian; Cooper, Valentino R.; Lee, Kyuho
- Reports on Progress in Physics, Vol. 78, Issue 6
Experimental Charge Density of α-Glycine at 23 K
journal, February 2000
- Destro, Riccardo; Roversi, Pietro; Barzaghi, Mario
- The Journal of Physical Chemistry A, Vol. 104, Issue 5
Works referencing / citing this record:
Insights into the Crystallization and Structural Evolution of Glycine Dihydrate by In Situ Solid‐State NMR Spectroscopy
journal, May 2018
- Cerreia Vioglio, Paolo; Mollica, Giulia; Juramy, Marie
- Angewandte Chemie, Vol. 130, Issue 22
Structure prediction drives materials discovery
journal, April 2019
- Oganov, Artem R.; Pickard, Chris J.; Zhu, Qiang
- Nature Reviews Materials, Vol. 4, Issue 5
High-pressure polymorphism in l -threonine between ambient pressure and 22 GPa
journal, January 2019
- Giordano, Nico; Beavers, Christine M.; Kamenev, Konstantin V.
- CrystEngComm, Vol. 21, Issue 30
Structural investigation and compression of a co-crystal of indomethacin and saccharin
journal, January 2019
- Connor, Lauren E.; Vassileiou, Antony D.; Halbert, Gavin W.
- CrystEngComm, Vol. 21, Issue 30
Pressure-induced isosymmetric phase transition in biurea
journal, January 2019
- Bull, Craig L.; Funnell, Nicholas P.; Ridley, Christopher J.
- CrystEngComm, Vol. 21, Issue 39
Cohesive properties of the crystalline phases of twenty proteinogenic α-aminoacids from first-principles calculations
journal, January 2019
- Červinka, Ctirad; Fulem, Michal
- Physical Chemistry Chemical Physics, Vol. 21, Issue 34
Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge
journal, September 2019
- Vologzhanina, Anna V.
- Crystals, Vol. 9, Issue 9
Insights into the Crystallization and Structural Evolution of Glycine Dihydrate by In Situ Solid‐State NMR Spectroscopy
journal, May 2018
- Cerreia Vioglio, Paolo; Mollica, Giulia; Juramy, Marie
- Angewandte Chemie International Edition, Vol. 57, Issue 22
Structure Prediction Drives Materials Discovery
text, January 2019
- Oganov, Artem; Pickard, Christopher; Zhu, Qiang
- Apollo - University of Cambridge Repository