Are racemic crystals favored over homochiral crystals by higher stability or by kinetics? Insights from comparative studies of crystalline stereoisomers

Journal of Organic Chemistry

Volumn 79, Issue 11, 2014, Pages 4809-4816

  Gavezzotti, Angelo ^a   Rizzato, Silvia ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; CRYSTALLINE MATERIALS; NUCLEATION; STEREOCHEMISTRY;

CAMBRIDGE STRUCTURAL DATABASES; COMPARATIVE STUDIES; CRYSTAL AND MOLECULAR STRUCTURE; ENERGY DIFFERENCES; HOMOGENEOUS NUCLEATION; INTRAMOLECULAR ENERGY; PROBABILISTIC FACTORS; QUANTITATIVE CORRELATION;

CRYSTAL SYMMETRY;

ARTICLE; CHEMICAL STRUCTURE; COMPARATIVE STUDY; CORRELATION ANALYSIS; CRYSTAL STRUCTURE; CRYSTALLIZATION; DIASTEREOISOMER; ENANTIOMER; KINETICS; QUANTITATIVE ANALYSIS; RACEMIC MIXTURE; STEREOISOMERISM; THERMODYNAMICS;

EID: 84902105391     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500528k     Document Type: Article

References (41)

1. Mullin, J. W. Crystallization, 4 th ed.; Elsevier: Amsterdam, 2001; p 295.
2. Perez-Garcia, L.; Amabilino, D. B. Chem. Soc. Rev. 2002, 31, 342-356
3. Lorenz, H.; Seidel-Morgenstern, A. Angew. Chem., Int. Ed. 2014, 53 (5) 1218-1250
4. Mislow, K. Bull. Soc. Chim. Belg. 1977, 86, 595-601
5. Allen, F. H. Acta Crystallogr. 2002, B58, 380-388
6. Cruz-Cabeza, A.; Bernstein, J. Chem. Rev. 2014, 114, 2170-2191
7. Dunitz, J. D.; Gavezzotti, A. J. Phys. Chem. B 2012, 116 (23) 6740-6750
8. Brock, C. P.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1991, 113, 9811-9820
9. Gavezzotti, A. New J. Chem. 2011, 35, 1360-1368
10. Gavezzotti, A. Mol. Phys. 2008, 106, 1473-1485
11. Gavezzotti, A. Molecular Aggregation, 2 nd ed.; Oxford University Press: Oxford, 2013; p 210.
12. Gavezzotti, A. Molecular Aggregation, 2 nd ed.; Oxford University Press: Oxford, 2013; Chapter 14.
13. See http://users.unimi.it/gavezzot/clp.zip. The doc folder has full documentation. Download of source programs is free for academic institutions.
14. EZOJUZ: Liu, F.; Cai, X.-L.; Yang, H.; Xia, X.-K.; Guo, Z.-Y.; Yuan, J.; Li, M.-F.; She, Z.-G.; Lin, Y.-C. Planta Med. 2010, 76, 185-189
15. MACLAE: Lo Presti, L.; Soave, R.; Destro, R. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2003, C59, o199-o201
16. Domiano, P.; Predieri, G.; Lanfranchi, M.; Tarasconi, P.; Palla, G. J. Chem. Soc., Perkin Trans. 2 1986, 521-524
17. MOHCES and MOLHI:F Gavrilov, V. V.; Shamsutdinov, M. N.; Kataeva, O. N.; Klochkov, V. V.; Litvinov, I. A.; Shtyrlin, Y. G.; Klimovitskii, E. N. J. Mol. Struct. 2008, 888) 173-179
18. Hirshfeld analysis was carried out with the aid of program CrystalExplorer (Version 3.1). Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Turner, M. J.; Jayatilaka, D.; Spackman, M. A. University of Western Australia, 2012.
19. Spackman, M. A.; McKinnon, J. J. CrystEngComm 2002, 4, 378-392
20. Nilewski, C.; Geisser, R. W.; Ebert, M. O.; Carreira, E. M. J. Am. Chem. Soc. 2009, 131 (43) 15866-15876
21. Nilewski, C.; Giesser, R. W.; Carreira, E. M. Nature 2009, 457, 573-576
22. Davey, R. J.; Schroeder, S. L. M.; ter Horst, J. H. Angew. Chem., Int. Ed. 2013, 52, 2166-2179
23. Viedma, C.; McBride, J. M.; Kahr, B.; Cintas, P. Angew. Chem. 2013, 125, 10739-10742
24. Dunitz, J. D.; Gavezzotti, A. Cryst. Growth Des. 2005, 5, 2180-2189
25. Harada, Y.; Iitaka, Y. Acta Crystallogr. 1974, B30, 726-730
26. Maguire, N. M.; Ford, A.; Clarke, S. L.; Eccles, K. S.; Lawrence, S. E.; Brossat, M.; Moody, T. S.; d Maguire, A. R. Tetrahedron: Asymmetry 2011, 22, 2144-2150
27. Betz, R.; Betzler, F.; Klufers, P. Acta Crystallogr. 2008, E64, o55
28. Jaunin, A.; Petcher, T. J.; Weber, H. P. J. Chem. Soc., Perkin Trans. 2 1977, 186-190
29. Fomulu, S.; Hendi, M. S.; Davis, R. E.; Wheeler, K. A. Cryst.Growth Des. 2002, 2, 637-644
30. Wallentin, C.-J.; Orentas, E.; Johnson, M. T.; Butkus, E.; Wendt, O. F.; Ohrstrom, L.; Warnmark, K. CrystEngComm 2009, 11, 1837-1841
31. Quast, H.; Becker, C.; Geissler, E.; Knoll, K.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Liebigs Ann. Chem. 1994, 109-120
32. Standard Monte Carlo simulations using a composite package optimized over the years for the treatment of organic crystals and liquids were carried out on liquids represented by 432 molecules plus boundary conditions, at constant (room) temperature and pressure. See ref 8 and: Gavezzotti, A. New J. Chem. 2013, 37, 2110-2119
33. LECFUV: Cramer, N.; Buchweitz, M.; Laschat, S.; Frey, W.; Baro, A.; Mathieu, D.; Richter, C.; Schwalbe, H. Chem. - Eur. J. 2006, 12, 2488-2503
34. van der Sluis, P.; Kroon, J. Acta Crystallogr. 1985, C41, 956-959
35. van der Sluis, P.; Kroon, J. Acta Crystallogr. 1989, C45, 1406-1408
36. Pallavicini, M.; Bolchi, C.; Di Pumpo, R.; Fumagalli, L.; Moroni, B.; Valoti, E.; Demartin, F. Tetrahedron: Asymmetry 2004, 15, 1659-1665
37. Desiraju, G. R.; Jagadese, J. V.; Ramanan, A. Crystal Engineering, a Textbook; IISc Press, World Scientific: Singapore, 2011.
38. Myerson, A. S.; Trout, B. L. Science 2013, 341, 855-856
39. Wallace, A. F.; Hedges, L. O.; Fernandez-Martinez, A.; Raiteri, P.; Gale, J. D.; Waychunas, G. A.; Whitelam, S.; Banfield, J. F.; De Yoreo, J. J. Science 2013, 341, 885-889
40. Salvalaglio, M.; Vetter, T.; Giberti, F.; Mazzotti, M.; Parrinello, M. J. Am. Chem. Soc. 2012, 134, 17221-17233
41. Salvalaglio, M.; Giberti, F.; Parrinello, M. Acta Crystallogr. 2014, C70, 132-136