Alteration of Polymorphic Selectivity through Different Crystallization Mechanisms Occurring in the Same Crystallization SolutionClick to copy article linkArticle link copied!
Abstract

We report a case in which two different crystallization mechanisms occurring in the same crystallization experiment are found to yield different polymorphic outcomes. In particular, we focus on crystallization of glycine from neutral aqueous solution. Crystallization in the bulk solution gives only the metastable α-polymorph, as observed in previous studies, whereas crystallization by evaporation of a thin film of the solution on the walls of the crystallization vessel is found to give rise to the thermodynamically stable γ-polymorph, and furthermore produces an uncharacteristic crystal morphology for this polymorph. A detailed set of control experiments are described that elucidate mechanistic details relating to the latter crystallization process. The fact that crystallization on the walls of a crystallization vessel can yield a different polymorphic outcome from crystallization in the bulk solution in the same experiment has potentially much wider significance with regard to other polymorphic systems.
*
To whom correspondence should be addressed. E-mail: harriskdm@ cardiff.ac.uk.
Cited By
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
This article is cited by 35 publications.
- Guangjun Han, Pui Shan Chow, and Reginald B. H. Tan . Effects of Common Inorganic Salts on Glycine Polymorphic Transformation: An Insight into Salt-Dependent Polymorphic Selectivity. Crystal Growth & Design 2016, 16
(11)
, 6499-6505. https://doi.org/10.1021/acs.cgd.6b01177
- Qi Jiang, Alexander G. Shtukenberg, Michael D. Ward, and Chunhua Hu . Non-Topotactic Phase Transformations in Single Crystals of β-Glycine. Crystal Growth & Design 2015, 15
(6)
, 2568-2573. https://doi.org/10.1021/acs.cgd.5b00187
- Sendhil K. Poornachary, Jose V. Parambil, Pui Shan Chow, Reginald B. H. Tan, and Jerry Y. Y. Heng . Nucleation of Elusive Crystal Polymorphs at the Solution–Substrate Contact Line. Crystal Growth & Design 2013, 13
(3)
, 1180-1186. https://doi.org/10.1021/cg301597d
- Yin Yani, Pui Shan Chow, and Reginald B. H. Tan . Glycine Open Dimers in Solution: New Insights into α-Glycine Nucleation and Growth. Crystal Growth & Design 2012, 12
(10)
, 4771-4778. https://doi.org/10.1021/cg300452n
- Abil E. Aliev, Sam E. Mann, Aisha S. Rahman, Paul F. McMillan, Furio Corà, Dinu Iuga, Colan E. Hughes, and Kenneth D. M. Harris . High-Resolution Solid-State 2H NMR Spectroscopy of Polymorphs of Glycine. The Journal of Physical Chemistry A 2011, 115
(44)
, 12201-12211. https://doi.org/10.1021/jp207592u
- Guangjun Han, Sendhil K. Poornachary, Pui Shan Chow, and Reginald B. H. Tan . Understanding Growth Morphology Changes of γ-Glycine and dl-Alanine Polar Crystals in Pure Aqueous Solutions. Crystal Growth & Design 2010, 10
(11)
, 4883-4889. https://doi.org/10.1021/cg100934f
- Jun Huang, Thomas C. Stringfellow and Lian Yu. Glycine Exists Mainly as Monomers, Not Dimers, in Supersaturated Aqueous Solutions: Implications for Understanding Its Crystallization and Polymorphism. Journal of the American Chemical Society 2008, 130
(42)
, 13973-13980. https://doi.org/10.1021/ja804836d
- Marie Côte, Colan E. Hughes, Talbir K. Austin, Philippe G. A. Rogueda, Zhigang Pan, Kenneth D. M. Harris and Peter C. Griffiths . Characterization of a Polymorphic System Exhibiting Substantial Variation of Solubility in a Fluorinated Solvent. The Journal of Physical Chemistry C 2008, 112
(37)
, 14570-14578. https://doi.org/10.1021/jp800848w
- Said Hamad, Colan E. Hughes, C. Richard A. Catlow and Kenneth D. M. Harris . Clustering of Glycine Molecules in Aqueous Solution Studied by Molecular Dynamics Simulation. The Journal of Physical Chemistry B 2008, 112
(24)
, 7280-7288. https://doi.org/10.1021/jp711271z
- In Sung Lee, Ki Tae Kim, Alfred Y. Lee and Allan S. Myerson. Concomitant Crystallization of Glycine on Patterned Substrates: The Effect of pH on the Polymorphic Outcome. Crystal Growth & Design 2008, 8
(1)
, 108-113. https://doi.org/10.1021/cg700890m
- Zhen Wang, Xiaoxiao Cui, Antonino Famulari, Javier Martí-Rujas, Benson M. Kariuki, Fang Guo. Solid-state stability of
Z
′ < 1 and
Z
′ = 2 polymorphs of
N
,
N
,
N
′,
N
′-tetrabenzylethylenediamine: a combined experimental and theoretical study. CrystEngComm 2022, 24
(45)
, 7924-7931. https://doi.org/10.1039/D2CE01174C
- Wen‐Chi Wang, Shun‐Fa Wang, Teruki Sugiyama. L‐serine polymorphism controlled by optical trapping with high‐repetition‐rate femtosecond laser pulses. Journal of the Chinese Chemical Society 2022, 69
(1)
, 200-210. https://doi.org/10.1002/jccs.202100269
- E.D. Gomes, A.E. Rodrigues. Crystallization of vanillin from kraft lignin oxidation. Separation and Purification Technology 2020, 247 , 116977. https://doi.org/10.1016/j.seppur.2020.116977
- Maria J. Vesga, David McKechnie, Paul A. Mulheran, Karen Johnston, Jan Sefcik. Conundrum of γ glycine nucleation revisited: to stir or not to stir?. CrystEngComm 2019, 21
(13)
, 2234-2243. https://doi.org/10.1039/C8CE01829D
- Kenneth D. M. Harris, Colan E. Hughes, P. Andrew Williams, Gregory R. Edwards-Gau. `NMR Crystallization':
in-situ
NMR techniques for time-resolved monitoring of crystallization processes. Acta Crystallographica Section C Structural Chemistry 2017, 73
(3)
, 137-148. https://doi.org/10.1107/S2053229616019811
- Guangjun Han, Pui Shan Chow, Reginald B. H. Tan. Salt-dependent growth kinetics in glycine polymorphic crystallization. CrystEngComm 2016, 18
(3)
, 462-470. https://doi.org/10.1039/C5CE01974E
- K. Renuka Devi, K. Srinivasan. Impact of malonic acid on the segregation of glycine polymorphs – Analytical assisted molecular approach. Crystal Research and Technology 2015, 50
(2)
, 171-178. https://doi.org/10.1002/crat.201400400
- Kenneth D.M. Harris, Colan E. Hughes, P. Andrew Williams. Monitoring the evolution of crystallization processes by in-situ solid-state NMR spectroscopy. Solid State Nuclear Magnetic Resonance 2015, 65 , 107-113. https://doi.org/10.1016/j.ssnmr.2014.11.004
- Kenneth D. M. Harris, Colan E. Hughes, P. Andrew Williams. In Situ Solid-State NMR Studies of Crystallization Processes. 2015, 31-53. https://doi.org/10.1007/978-4-431-55555-1_3
- Colan E. Hughes, P. Andrew Williams, Victoria L. Keast, Vasileios G. Charalampopoulos, Gregory R. Edwards-Gau, Kenneth D. M. Harris. New in situ solid-state NMR techniques for probing the evolution of crystallization processes: pre-nucleation, nucleation and growth. Faraday Discussions 2015, 179 , 115-140. https://doi.org/10.1039/C4FD00215F
- Yohei Kamano, Kazunori Kadota, Atsuko Shimosaka, Yoshiyuki Shirakawa, Jusuke Hidaka. Quantitative Evaluation of Glycine Crystal Growth from Solution by a Phase Field Simulation. Journal of Chemical Engineering of Japan 2015, 48
(10)
, 821-828. https://doi.org/10.1252/jcej.15we030
- Nathan Duff, Yuba Raj Dahal, Jeremy D. Schmit, Baron Peters. Salting out the polar polymorph: Analysis by alchemical solvent transformation. The Journal of Chemical Physics 2014, 140
(1)
https://doi.org/10.1063/1.4853775
- Gianluca Di Profio, Mika T. Reijonen, Rocco Caliandro, Antonietta Guagliardi, Efrem Curcio, Enrico Drioli. Insights into the polymorphism of glycine: membrane crystallization in an electric field. Physical Chemistry Chemical Physics 2013, 15
(23)
, 9271. https://doi.org/10.1039/c3cp50664a
- Anna Jawor-Baczynska, Barry D. Moore, Han Seung Lee, Alon V. McCormick, Jan Sefcik. Population and size distribution of solute-rich mesospecies within mesostructured aqueous amino acid solutions. Faraday Discussions 2013, 167 , 425. https://doi.org/10.1039/c3fd00066d
- N. V. Surovtsev, S. V. Adichtchev, V. K. Malinovsky, A. G. Ogienko, V. A. Drebushchak, A. Yu. Manakov, A. I. Ancharov, A. S. Yunoshev, E. V. Boldyreva. Glycine phases formed from frozen aqueous solutions: Revisited. The Journal of Chemical Physics 2012, 137
(6)
https://doi.org/10.1063/1.4739532
- Aniruddh Singh, In Sung Lee, Kitae Kim, Allan S. Myerson. Crystal growth on self-assembled monolayers. CrystEngComm 2011, 13
(1)
, 24-32. https://doi.org/10.1039/C0CE00030B
- Elise J. C. de Vries, Demetrius C. Levendis, Hayley A. Reece. A hexagonal solvate of the neurotransmitter γ-aminobutyric acid. CrystEngComm 2011, 13
(10)
, 3334. https://doi.org/10.1039/c0ce00803f
- Said Hamad, C. Richard A. Catlow. Are glycine cyclic dimers stable in aqueous solution?. CrystEngComm 2011, 13
(13)
, 4391. https://doi.org/10.1039/c0ce00877j
- Mihasina Rabesiaka, Mehrez Sghaier, Bernard Fraisse, Catherine Porte, Jean-Louis Havet, Emma Dichi. Preparation of glycine polymorphs crystallized in water and physicochemical characterizations. Journal of Crystal Growth 2010, 312
(11)
, 1860-1865. https://doi.org/10.1016/j.jcrysgro.2010.03.011
- Colan E. Hughes, Kenneth D. M. Harris. Direct observation of a transient polymorph during crystallization. Chemical Communications 2010, 46
(27)
, 4982. https://doi.org/10.1039/c0cc01007c
- Andrew D. Bond. Polymorphism in molecular crystals. Current Opinion in Solid State and Materials Science 2009, 13
(3-4)
, 91-97. https://doi.org/10.1016/j.cossms.2009.06.004
- Harry G. Brittain. Polymorphism and Solvatomorphism 2007. Journal of Pharmaceutical Sciences 2009, 98
(5)
, 1617-1642. https://doi.org/10.1002/jps.21518
- Colan E. Hughes, Kenneth D. M. Harris. The effect of deuteration on polymorphic outcome in the crystallization of glycine from aqueous solution. New Journal of Chemistry 2009, 33
(4)
, 713. https://doi.org/10.1039/b819199a
- S. L. Price. Computational prediction of organic crystal structures and polymorphism. International Reviews in Physical Chemistry 2008, 27
(3)
, 541-568. https://doi.org/10.1080/01442350802102387
- Sarah L. Price. From crystal structure prediction to polymorph prediction: interpreting the crystal energy landscape. Physical Chemistry Chemical Physics 2008, 10
(15)
, 1996. https://doi.org/10.1039/b719351c
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.