Citation: Haiying Wang, Andrew C.-H. Sue. How to Visually Identify Homochiral Crystals[J]. University Chemistry, ;2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004 shu

How to Visually Identify Homochiral Crystals

Haiying Wang ^1,, ,
Andrew C.-H. Sue ²

1.
Sichuan Key Laboratory of Medical Imaging, North Sichuan Medical College, Nanchong 637000, Sichuan Province, China;
2.
College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, China

Corresponding author: Haiying Wang, hywang@nsmc.edu.cn
Received Date: 1 September 2023

During the crystallization process of certain racemic compounds, spontaneous resolution can lead to distinctive external appearances of enantiomeric crystal forms. This article offers a comprehensive overview and delineates four methods for identification, namely, examining hemihedral faces, assessing macromorphology, employing circular polarization, and analyzing surface topography. These identification techniques serve as invaluable tools and viewpoints for studying the crystallization behavior of chiral compounds, holding significant potential across diverse applications in pharmaceutical production, materials science, and chemical synthesis.
- Spontaneous resolution,
- Hemihedral faces,
- Macromorphology,
- Circular polarization,
- Surface topography
1. [1]
  Flack, H. D. Helv. Chim. Acta 2003, 86, 905.
2. [2]
  Ramsay, O. B. Stereochemistry. Heyden & Son Ltd.: London, UK, 1981.
3. [3]
  Flack, H. Acta Cryst. 2009, A65, 371.
4. [4]
  Concentrates. Chem. Eng. News 2003, 81, 27.
5. [5]
  Pérez-García, L.; Amabilino, D. B. Chem. Soc. Rev. 2002, 31, 342.
6. [6]
  Pérez-García, L.; Amabilino, D. B. Chem. Soc. Rev. 2007, 36, 941.
7. [7]
  Collison, D. Cryst. Rev. 2017, 24, 144.
8. [8]
  Lan, Z. P.; Lai, X.; Roberts, K.; Klapper, H. Cryst. Growth Des. 2014, 14, 6084.
9. [9]
  Szurgot, J.; Szurgot, M. Cryst. Res. Technol. 1995, 30, 71.
10. [10]
  Schmieder, P.; Denysenko, D.; Grzywa, M.; Baumgärtner, B.; Senkovska, I.; Kaskel, S.; Sastre, G.; van Wüllen, L.; Volkmer, D. Dalton Trans. 2013, 42, 10786.
11. [11]
  Kawasaki, T.; Nakaoda, M.; Kaito, N.; Sasagawa, T.; Soai, K. Orig. Life Evol. Biosph. 2010, 40, 65.
12. [12]
  Coquerel, G.; Petit, S. J. Cryst. Growth 1993, 130, 173.
13. [13]
  Kress, R. B.; Duesler, E. N.; Etter, M. C.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1980, 102, 7709.
14. [14]
  Curtin, D. Y.; Paul, I. C. Chem. Rev. 1981, 81, 525.
15. [15]
  Kauffman, G. B.; Myers, R. D. J. Chem. Edu. 1975, 52, 777.
16. [16]
  Van Rosmalen, G. M.; Bennema, P. J. Cryst. Growth 1990, 99, 1053.
17. [17]
  Coquerel, G.; Perez, G.; Hartman, P. J. Cryst. Growth 1988, 88, 511.
18. [18]
  Davey, R. J.; Black, S. N.; Williams, L. J.; McEwan, D.; Sadler, D. E. J. Cryst. Growth 1990, 102, 97.
19. [19]
  Weissbuch, I.; Leiserowitz, L.; Lahav, M. Chirality 2008, 20, 736.
20. [20]
  Addadi, L.; Weinstein, S.; Gati, E.; Weissbuch, I.; Lahav, M. J. Am. Chem. Soc. 1982, 104, 4610.
21. [21]
  Addadi, L.; Gati, E.; Lahav, M. J. Am. Chem. Soc. 1981, 103, 1251.
22. [22]
  Andrade-Gamboa, J. J. Chem. Edu. 2007, 84, 1783.
23. [23]
  Cuccia, L. A.; Koby, L.; Ningappa, J. B.; Dakessian, M. J. Chem. Edu. 2005, 82, 1043.
24. [24]
25. [25]
  Andrade-Gamboa, J. J. Chem. Edu. 2007, 84, 1783.
26. [26]
  Orme, C. A.; Noy, A.; Wierzbicki, A.; McBride, M. T.; Grantham, M.; Teng, H. H.; Dove, P. M.; De Yoreo, J. J. Nature 2001, 411, 775.
27. [27]
  Weissbuch, I.; Addadi, L.; Lahav, M.; Leiserowitz, L. Science 1991, 253, 637.
28. [28]
  Lin, C. T.; Curtin, D. Y.; Paul, I. C. J. Am. Chem. Soc. 1974, 96, 6199.
29. [29]
  Hanein, D.; Geiger, B.; Addadi, L. Science 1994, 263, 1413.
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