Glycine Polymorphism in Nanoscale Crystallization Chambers
Source abstract
Abstract
Crystallization of glycine by evaporation of aqueous solutions in nanometer-scale channels of controlled-pore glass (CPG) powders and porous polystyrene-poly(dimethyl acrylamide) (p-PS-PDMA) monoliths, the latter prepared by etching polylactide (PLA) from aligned PS-PDMA-PLA triblock copolymers, preferentially results in exclusive formation of the β polymorph, which is not observed during crystallization in bulk form under identical conditions. X-ray diffraction (XRD) reveals that the dimensions of the embedded crystals are commensurate with the pore diameter of the matrix. β-Glycine persists for at least one year in CPG and p-PS-PDMA with pore diameters less than 24 nm, but it transforms slowly to α-glycine over several days when confined within 55 nm CPG. Moreover, variable temperature XRD reveals that β-glycine nanocrystals embedded within CPG are stable at temperatures at which bulk β-glycine ordinarily transforms to the α form. XRD and differential scanning calorimetry (DSC) reveal the melting of glycine nanocrystals within CPG below the temperature at which bulk glycine melts with concomitant decomposition. The melting point depression conforms to the Gibb-Thompson equation, with the melting points decreasing with decreasing pore size. This behavior permits an estimation of the melting temperature of bulk β-glycine, which cannot be measured directly owing to its metastable nature. Collectively, these results demonstrate size-dependent polymorphism for glycine and the ability to examine certain thermal properties under nanoscale confinement that cannot be obtained in bulk form. The observation of β-glycine at nanometer-scale dimensions suggests that glycine crystallization likely involves formation of β nuclei followed by their transformation to the other more stable forms as crystal size increases, in accord with Ostwald’s rule of stages.
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Research context
OpenAlex topics: Crystallization and Solubility Studies · Analytical Chemistry and Chromatography · Enzyme Structure and Function
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Chemical Engineering and Materials Science and the Department of Chemistry, 207 Pleasant Street SE, University of Minnesota, Minneapolis, Minnesota 55455-0431, and the Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, New York, New York 10003-6688
References (82)
Show source-provided references
1. Loisel C. · J. Am. Oil Chem. Soc. · 1998 · 75 · 42510.1007/s11746-998-0245-y ↗
2. Yu L. · J. Am. Chem. Soc. · 2000 · 122 · 58510.1021/ja9930622 ↗
3. Chemburkar S. R. · Org. Process Res. Dev. · 2000 · 4 · 41310.1021/op000023y ↗
4. Brittain J. G. · 1999
5. Byrn S. R. · Pharm. Res. · 1995 · 12 · 94510.1023/A:1016241927429 ↗
6. Rodrigeuz-Hornedo N. · J. Pharm. Sci. · 1999 · 88 · 65110.1021/js980490h ↗
7. Khoshkhoo S. · J. Phys. D: Appl. Phys. · 1993 · 26 · B9010.1088/0022-3727/26/8B/013 ↗
8. Kitamura M. · J. Cryst. Growth · 2002 · 237 · 220510.1016/S0022-0248(01)02277-1 ↗
9. Davey R. J. · J. Am. Chem. Soc. · 1997 · 119 · 176710.1021/ja9626345 ↗
10. Last J. A. · J. Phys. Chem. B · 1999 · 103 · 672310.1021/jp984101j ↗
11. Price C. P. · J. Am. Chem. Soc. · 2005 · 127 · 551210.1021/ja042561m ↗
12. Bonafede S. J. · J. Am. Chem. Soc. · 1995 · 117 · 785310.1021/ja00135a001 ↗
13. Bernstein J. · 2002
14. Oxtoby D. W. · Acc. Chem. Res. · 1998 · 31 · 9110.1021/ar9702278 ↗
15. Jackson C. L. · J. Chem. Phys. · 1990 · 93 · 900210.1063/1.459240 ↗
16. Patrick W. A. · J. Phys. Chem. · 1938 · 42 · 36910.1021/j100898a006 ↗
17. Borisov B. F. · J. Phys. Condens. Matter · 1997 · 9 · 337710.1088/0953-8984/9/16/010 ↗
18. Buffat Ph. · Phys. Rev. A · 1976 · 13 · 228710.1103/PhysRevA.13.2287 ↗
19. Reinnie G. K. · J.Chem. Soc., Faraday Trans. 1 · 1977 · 73 · 68010.1039/f19777300680 ↗
20. Christenson H. K. · J. Phys.: Condens. Matter · 2001 · 13 · R95−R133
21. Jackson C. L. · Chem. Mater. · 1996 · 8 · 212810.1021/cm9601188 ↗
22. Ajayan P. M. · Nature · 1993 · 361 · 33310.1038/361333a0 ↗
23. Prasad R. · Phil. Mag. Lett. · 1994 · 70 · 35710.1080/09500839408240501 ↗
24. Ha J.-M. · J. Phys. Chem. B · 2005 · 109 · 139210.1021/jp045488v ↗
25. Ha J.-M. · J. Am. Chem. Soc. · 2004 · 126 · 338210.1021/ja049724r ↗
26. Ha, J.M.Ph.D. Thesis, University of Minnesota, 2006.
27. Beiner M. · Nano Lett. · 2007 · 7 · 138110.1021/nl0705081 ↗
28. Rengarajan G. T. · J. Mat. Chem. · 2008 · 18 · 253710.1039/b804266g ↗
29. Chang B. S. · Pharm. Res. · 1996 · 13 · 24310.1023/A:1016043114998 ↗
30. Bush L. · Semin. Hematol. · 1998 · 35 · 18
31. Nail S. L. · Pharm. Biotech. · 2002 · 14 · 28110.1007/978-1-4615-0549-5_6 ↗
32. Kuan Y.-J. · Astrophys. J. · 2003 · 593 · 84810.1086/375637 ↗
33. Snyder L. E. · Astrophys. J. · 2005 · 619 · 91410.1086/426677 ↗
34. Elsila J. E. · Astrophys. J. · 2007 · 660 · 91110.1086/513141 ↗
35. Albrecht G. · J. Am. Chem. Soc. · 1939 · 61 · 108710.1021/ja01874a028 ↗
36. Marsh R. E. · Acta Crystallogr. · 1958 · 11 · 65410.1107/S0365110X58001717 ↗
37. Destro R. · J. Phys. Chem. A · 2000 · 104 · 104710.1021/jp993505o ↗
38. Jonsson P.-G. · Acta Crystallogr. B · 1972 · 28 · 182710.1107/S0567740872005096 ↗
39. Power L. F. · Acta Crystallogr. B · 1976 · 32 · 1110.1107/S0567740876002227 ↗
40. Legros J.-P. · Acta Crystallogr. B · 1980 · 36 · 305210.1107/S0567740880010783 ↗
41. Boldyreva E. V. · Z. Kristallogr. · 2003 · 218 · 36610.1524/zkri.218.5.366.20729 ↗
42. Pervolich G. L. · J. Therm. Anal. Calorim. · 2001 · 66 · 69910.1023/A:1013179702730 ↗
43. Dawson A. · Cryst. Growth Des. · 2005 · 5 · 141510.1021/cg049716m ↗
44. Marsh R. E. · Acta Crystallogr. · 1958 · 11 · 65410.1107/S0365110X58001717 ↗
45. Iitaka Y. · Acta Crystallogr. · 1961 · 14 · 110.1107/S0365110X61000012 ↗
46. Iitaka Y. · Acta Crystallogr. · 1960 · 13 · 3510.1107/S0365110X60000066 ↗
47. Boldyreva E. V. · J. Therm. Anal. Calorim. · 2003 · 73 · 40910.1023/A:1025405508035 ↗
48. Boldyreva E. V. · J. Therm. Anal. Calorim. · 2003 · 73 · 41910.1023/A:1025457524874 ↗
49. Chongprasert S. · J. Pharm. Sci. · 2001 · 90 · 172010.1002/jps.1121 ↗
50. Takagi S. · Bull. Chem. Soc. Jpn. · 1959 · 32 · 8410.1246/bcsj.32.84 ↗
51. deKruif C. G. · J. Chem. Thermodyn. · 1979 · 11 · 65110.1016/0021-9614(79)90030-2 ↗
52. Raabe G. · Z. Naturforsch. · 2000 · 55 · 60910.1515/zna-2000-6-708 ↗
53. Rodante F. · Thermochim. Acta · 1992 · 194 · 19710.1016/0040-6031(92)80018-R ↗
54. Wesolowski M. · J. Therm. Anal. Calorm. · 2005 · 82 · 30710.1007/s10973-005-0895-z ↗
55. Li J. · J. Anal. Appl. Pyrolysis · 2007 · 80 · 24710.1016/j.jaap.2007.03.001 ↗
56. Torbeev V. Y. · Cryst. Growth Des. · 2005 · 5 · 219010.1021/cg050200s ↗
57. Landau E. · J. Am. Chem. Soc. · 1989 · 111 · 143610.1021/ja00186a044 ↗
58. Lee A. Y. · J. Am. Chem. Soc. · 2005 · 127 · 1498210.1021/ja055416x ↗
59. Zaccaro J. · Cryst. Growth Des. · 2001 · 1 · 510.1021/cg0055171 ↗
60. Kang J. F. · Langmuir · 2000 · 16 · 379110.1021/la9914054 ↗
61. Chattopadhyay S. · Cryst. Growth Des. · 2005 · 5 · 52310.1021/cg0497344 ↗
62. Lee I. S. · Cryst. Growth Des. · 2008 · 8 · 10810.1021/cg700890m ↗
63. Sun X. · Cryst. Growth Des. · 2006 · 6 · 68410.1021/cg050460+ ↗
64. Rzayev J. · Macromolecules · 2005 · 38 · 310.1021/ma047870b ↗
65. Rzayev J. · J. Am. Chem. Soc. · 2005 · 127 · 1337310.1021/ja053731d ↗
66. Ostwald W. Z. · Z. Phys. Chem. · 1897 · 22 · 28910.1515/zpch-1897-2233 ↗
67. Cullity B. D. · 1978
68. Klug H. P. · 1974
69. Brandrup J. · 1999
70. Bouchard A. · J. Chem. Eng. Data · 2007 · 52 · 162610.1021/je700014k ↗
71. Traces of the carboxyl O-H stretch, alkane stretch and amine stretch were present exclusively for the glycine loaded CPG. Due to the small mass of glycine within the CPG pores and the instrumental limits on the amount of CPG in each IR sample, the glycine absorption peaks were weak.
72. Hamilton, B. D.; Hillmyer, M. A.; Weissbuch, I.; Lahav, M.; Ward, M. D.,manuscript in preparation.
73. In a small number (<10%) of the CPG and p-PS-PDMA samples one or two intense, discrete spots corresponding to α-glycine appeared in the 2D XRD data in addition to the β-glycine nanocrystal arcs. The diffraction peaks widths for these α-glycine crystals indicating crystal sizes larger than the maximum estimable size of 30 nm, suggesting that these α-glycine crystals were bulk crystals on the surfaces of the porous materials. The presence of these bulk crystals appeared to have no impact on the nanocrystal behavior.
74. Drebushchak T. N. · Acta Crystallogr. · 2002 · 58 · o634
75. Drebushchak T. N. · J. Struct. Chem. · 2002 · 43 · 83510.1023/A:1022885510109 ↗
76. For example, the expected amount of glycine embedded within 1 gram of 24 nm CPG with total pore volume 0.95 cm3/g, using a 15% glycine solution (weight percent), is 0.167 g. Based on the surface area of the pores in 24 nm CPG (78.8 m2/g) and the density of glycine (1.58 g/cm3), the thickness of a uniform glycine layer on the pore walls would be 1.34 nm.
77. The respective absolute mass losses for the CPG samples were 2.2% for 7.5 nm CPG, 4.2% for 24 nm CPG, and 6.5% for 55 nm CPG.
78. The DSC peak maxima occurred at 210 °C for 7.5 nm CPG, 219 °C for 24 nm CPG, and 229 °C for 55 nm CPG.
79. aThis form of the Gibbs-Thompson equation assumes constant density, constant heat of fusion, and a crystal-pore wall contact angle of 180°. The assumption of a 180° contact angle, however, may not always be valid. See
80. Scherer G. W. · Cem. Concr. Res. · 1999 · 29 · 134710.1016/S0008-8846(99)00002-2 ↗
81. The slope of the linear fit was −155 ± 44 °C/nm−1. The error bars represent 1 esd based on the linear regression analysis of three data points for each pore size. This error in the melting point can be discerned readily by varying the slope of the fitted line within the limits imposed by all three pore sizes.
82. For example, the DSC data for the 55 nm CPG beads containing embedded β-glycine nanocrystals, which were prepared by imbibing an 18% (weight percent) glycine solution, exhibited an endothermic peak corresponding to a total enthalpy of 0.128 kJ/g total sample (i.e. CPG beads plus contents; seeSupporting Informationfor all samples). The contribution to the endothermic heat flow expected from the known enthalpy of water vaporization (ΔĤvap= 2.28 kJ/g) and the amount of water presumed trapped within the pores is 0.210 kJ/g total sample. Endothermic glycine melting would be expected to add to this heat flow. As such the measured heat flow is substantially less than expected based on the contents within the pores. This suggests an exothermic process that offsets the endothermic contributions, possibly the concomitant solidification of a higher melting amorphous phase. Based on the heat flow expected from the trapped water and the amount embedded glycine (0.21 g/g total sample) the exothermic enthalpy of solidification of the amorphous phase would need to be 30 kJ/mol greater than the melting enthalpy of β-glycine, which seems unreasonably large. This difference would be smaller if the measured heat flow contribution from trapped water was reduced due to a slow and gradual release of water, prior to the onset temperature, which may not be readily detectable.