Chiral symmetry breaking phenomenon caused by a phase transition

Symmetry

Volumn 2, Issue 1, 2010, Pages 112-135

  Tamura, Rui ^a   Iwama, Sekai ^a   Takahashi, Hiroki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Chiral separation; Enantiomeric resolution; Epitaxial transition; Mixed crystal; Optical resolution; Polymorphic transition; Preferential enrichment

Indexed keywords

EID: 79953857588     PISSN: None     EISSN: 20738994     Source Type: Journal    
DOI: 10.3390/sym2010112     Document Type: Review

References (53)

1. Mainzer, K. Symmetry and Complexity: The Sprit and Beauty of Nonlinear Science; World Scientific: Singapore, 2005.
2. Kauffman, S. Investigations; Oxford University Press: Oxford, UK, 2000.
3. Waldrop, M.M. Complexity; Simon &Schuster: New York, NY, USA, 1992.
4. Pérez-García, L.; Amabilino, D.B. Spontaneous Resolution Under Supramolecular Control. Chem. Soc. Rev. 2002, 31, 342-356.
5. Ushio, T.; Tamura, R.; Takahashi, H.; Yamamoto, K. Unusual Enantiomeric Resolution Phenomenon Observed upon Recrystallization of a Racemic Compound. Angew. Chem. Int. Ed. Engl. 1996, 35, 2372-2374.
6. Ushio, T.; Tamura, R.; Azuma, N.; Nakamura, K.; Toda, F.; Kobayashi, K. Polymorphism of Compounds Existing as Both Racemic Compounds Crystals and Mixed Crystals of Enantiomers. Mol. Cryst. Liq. Cryst. 1996, 276, 245-252.
7. Tamura, R.; Takahashi, H.; Fujimoto, D.; Ushio, T. Mechanism and Scope of Preferential enrichment, a Symmetry-Breaking Enantiomeric Resolution Phenomenon. Top. Curr. Chem. 2007, 269, 53-82.
8. Tamura, R.; Ushio, T. Preferential Enrichment: A Dynamic Enantiomeric Resolution Phenomenon Caused by Polymorphic Transition During Crystallization. In Enantiomer Separation: Fundamentals and Practical Methods, Toda, F., Ed.; Kluwer: Dordrecht, The Netherlands, 2004; pp. 135-163.
9. Jacques, J.; Collet, A.; Wilen, S.H. Enantiomers, Racemates and Resolutions; Krieger: Malabar, FL, USA, 1994.
10. CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation Kozma, D., Ed.; CRC Press: Boca Raton, FL, USA, 2001.
11. Kinbara, K.; Saigo, K. Chiral Discrimination during Crystallization. Top. Stereochem. 2003, 23, 207-265.
12. Sakai, K.; Sakurai, R.; Nohira, H. New Resolution Technologies Controlled by Chiral Discrimination Mechanisms. Top. Curr. Chem. 2007, 269, 199-231.
13. Kellogg, R.M.; Kaptein, B.; Vries, T.R. Dutch Rresolution of Racemates and the Roles of Solid Solution Formation and Nucleation Inhibition. Top. Curr. Chem. 2007, 269, 159-197.
14. Toda, F. Optical Resolutions by Inclusion Complexation with a Chiral Host Compound. In Enantiomer Separation: Fundamentals and Practical Methods, Toda, F., Ed.; Kluwer: Dordrecht, The Netherlands, 2004; pp. 1-47.
15. Collet, A.; Brienne, M.-J.; Jacques, J. Optical Resolution by Direct Crystallization of Enantiomer Mixtures. Chem. Rev. 1980, 80, 215-230.
16. Collet, A. Optical Resolution. In Comprehensive Supramolecular Chemistry; Reinhoudt, D.N., Ed.; Pergamon: Oxford, UK, 1996; Vol. 10, pp.113-149.
17. Kinbara, K.; Hashimoto, Y.; Sukegawa, M.; Nohira, H.; Saigo, K. Crystal Structures of the Salts of Chiral Primary Amines with Achiral Carboxylic Acids: Recognition of the Commonly-Occurring Supramolecular Assemblies of hydrogen-Bond Networks and Their Role in the Formation of Conglomerates. J. Am. Chem. Soc. 1996, 118, 3441-3449.
18. Coquerel, G. Preferential Crystallization. Top. Curr. Chem. 2007, 269, 1-51.
19. Eliel, E.; Wilen, S.H.; Mander, L.N. Stereochemistry of Organic Compounds; Wiley: New York, NY, USA, 1994; pp.297-464.
20. Tamura, R.; Takahashi, H.; Hirotsu, K.; Nakajima, Y.; Ushio, T.; Toda, F. Unusual Disordered Crystal Structure of a Racemate Exhibiting a Novel Enantiomeric Resolution: Preferential Enrichment. Angew. Chem. Int. Ed. Engl. 1998, 37, 2876-2878.
21. Tamura, R.; Fujimoto, D.; Lepp, Z.; Misaki, K.; Miura, H.; Takahashi, H.; Ushio, T.; Nakai, T.; Hirotsu, K. Mechanism of Preferential Enrichment, an Unusual Enantiomeric Resolution Phenomenon Caused by Polymorphic Transition during Crystallization of Mixed Crystals Composed of Two Enantiomers. J. Am. Chem. Soc. 2002, 124, 13139-13153.
22. 2)H--O Interaction on the Control of a Crystal Structure. Cryst. Growth Des. 2003, 3, 973-979.
23. Tamura R, Mizuta M, Yabunaka S, Fujimoto D, Ariga T, Okuhara S, Ikuma N, Takahashi H, Tsue H. Induction and Inhibition of Preferential Enrichment by Controlling the Mode of the Polymorphic Transition with Seed Crystals. Chem. Eur. J. 2006, 12, 3515-3527.
24. Horiguchi, M.; Okuhara, S.; Shimano, E.; Fujimoto, D.; Takahashi, H.; Tsue, H.; Tamura, R. Control of the Mode of Polymorphic Transition Inducing Preferential Enrichment by Modifying the Molecular Structure or Adding Seed Crystals: Significant Influence of CH/F Hydrogen Bonds. Cryst. Growth Des. 2008, 8, 540-548.
25. Horiguchi, M.; Okuhara, S.; Shimano, E.; Fujimoto, D.; Takahashi, H.; Tsue, H.; Tamura, R. Mechanistic Flexibility of Solvent-Assisted Solid-to-Solid Polymorphic Transition Causing Preferential Enrichment: Significant Contribution of π/π and CH/π Interactions as Well as Hydrogen Bonds. Cryst. Growth Des. 2007, 7, 1643-1652.
26. Bernstein, J. Polymorphism in Molecular Crystals; Oxford University Press: Oxford, UK, 2002.
27. Polymorphism in Pharmaceutical Solids, Drugs and the Pharmaceutical Sciences; Brittain, H.G., Ed.; Marcel Dekker: New York, NY, USA, 1999; Vol. 95.
28. Bernstein, J.; Davey, R.J.; Henck, J.-O. Concomitant Polymorphs. Angew. Chem. Int. Ed. Engl. 1999, 38, 3440-3461.
29. Dunitz, J.D., Bernstein, J. Disappearing Polymorphs. Acc. Chem. Res. 1995, 28, 193-200.
30. McCrone, W.C. Polymorphism. In Physics and Chemistry of the Organic Solid State; Fox, D.; Labes, M.M.; Weissberger, A., Eds.; Interscience: New York, NY, USA, 1965; Vol. II, pp.726-767.
31. Ostwald, W. Grundriss der Allgemeinen Chemie; W. Engelmann: Leipzig, 1899.
32. Parkinson, G.M.; Thomas, J.M.; Williams, J.O.; Goringe, M.J.; Hobbs, L.W. The Suggested Role of Partial Dislocations in the Single Crystal-Single Crystal Phase Transition of a Cyclo-octane Molecular Cationic Salt. J. Chem. Soc., Perkin 2 1976, 836-838.
33. Tamura, R.; Ushio, T.; Nakamura, K.; Takahashi, H.; Azuma, N; Toda, F. Ideal Enantiomeric Resolution by Recrystallization of a Racemic Compound. Enantiomer 1997, 2, 277-280.
34. Tamura, R., Ushio, T.; Takahashi, H.; Nakamura, K.; Azuma, N.; Toda, F.; Endo, K. Ideal Enantiomeric Resolution of a Racemic Compound (Part 4): Relationship Between Enantiomeric Resolution Phenomenon and Crystal Properties. Chirality 1997, 9, 220-224.
35. Takahashi, H.; Tamura, R.; Ushio, T.; Nakajima, Y.; Hirotsu, K. Ideal Enantiomeric Resolution (Preferential Enrichment) by Recrystallization of a Racemic Compound. V: Relationship Between Preferential Enrichment and Crystal Structures. Chirality 1998, 10, 705-710.
36. Tamura, R.; Takahashi, H.; Hirotsu, K.; Nakajima, Y.; Ushio, T. Preferential Enrichment and Crystal Structure. Mol. Cryst. Liq. Cryst. 2001, 356, 185-194.
37. Tamura, R.; Takahashi, H.; Ushio, T.; Nakajima, Y.;Hirotsu, K.; Toda, F. Ideal Enantiomeric Resolution (Preferential Enrichment) by Recrystallization of a Racemic Compound (Part 6): Hydrogen Bonding Mode in the Crystal Structure. Enantiomer 1998, 3, 149-157.
38. Tamura, R.; Takahashi, H.; Miura, H.; Lepp, Z.; Nakajima Y.; Hirotsu, K.; Ushio, T. Comparison of Crystal Structures of New Racemic Chiral Compounds Showing and Not Showing the Phenomenon of Preferential Enrichment. Supramol. Chem. 2001, 13, 71-78.
39. Takahashi, H.; Tamura, R.; Lepp, Z.; Kobayashi, K.; Ushio, T. Preferential Enrichment: An Essential Crystal Structure. Enantiomer 2001, 6, 57-66.
40. Takahashi, H.; Tamura, R.; Fujimoto, D.; Lepp, Z.; Kobayashi, K.; Ushio, T. Preferential Enrichment: Full Crystallographic Analysis of the Unusual Phenomenon in the Mixed Crystals' Version. Chirality 2002, 14, 541-547.
41. Takahashi, H.; Tamura, R.; Yabunaka, S.; Ushio, T. Crystal Structure of a New Racemate Showing Preferential Enrichment: Evidence for the Existence as a Racemic Mixed Crystal Composed of the Two Enantiomers. Mendeleev Commun. 2003, 119-121.
42. Miura, H.; Ushio, T.; Nagai, K.; Fujimoto, D.; Lepp, Z.; Takahashi, H.; Tamura, R. Crystallization of a Desired Metastable Polymorph by Pseudoseeding, Crystal Structure Solution from Its Powder X-ray Diffraction Data, and Confirmation of Polymorphic Transition. Cryst. Growth Des. 2003, 3, 959-965.
43. 2) Coulombic Donor-Acceptor Attraction to the Buildup of a Crystal Structure. Mendeleev Commun. 2004, 239-241.
44. Fujimoto, D.; Takahashi, H.; Ariga, T.; Tamura, R. Preferential Enrichment: Significant Influence of Minor Molecular Modification on the Mode of Polymorphic Transition during Crystallization. Chiraliry, 2006, 18, 188-195.
45. Horiguchi, M.; Yanunaka, S.; Iwama, S.; Shimano, E.; Lepp, Z.; Takahashi, H.; Tsue, H.; Tamura, R. Case Study on the Effects of Molecular Structure on the Mode of Polymorphic Transition Inducing Preferential Enrichment. Eur. J. Org. Chem.2008, 3496-3505.
46. Maruyama, S.; Ooshima, H. Crystallization Behavior of Taltirelin Polymorphs in a Mixture of Water and Methanol. J. Crystal Growth 2000, 212, 239-245.
47. Kitamura, M.; Ueno, S.; Sato, K. Molecular Aspects of the Polymorphic Crystallization of Amino Acids and Lipids. In Crystallization Processes, Ohtaki, H., Ed.; Wiley: Chichester, UK, 1998; pp. 99-129.
48. Kitamura, M. Polymorphism in the Crystallization of L-Glutamic Acid. J. Crystal Growth 1989, 96, 541-546.
49. Dobashi, A.; Saito, N.; Motoyama, Y.; Hara, S. Self-Induced Nonequivalence in the Association of D- and L-Amino Acid Derivatives. J. Am. Chem. Soc. 1986, 108, 307-308.
50. Jursic B.S.; Goldberg, S.I. Enantiomer Discrimination Arising from Solute-Solute Interactions in Partially Resolved Chloroform Solutions of Chiral Carboxamides. J. Org. Chem. 1992, 57, 7172-7174.
51. Harger, M.J.P. Proton Magnetic Resonance Non-equivalence of the Enantiomers of Alkylphenylphosphinic Amides. J. Chem. Soc., Perkin Trans. 2 1977, 1882-1887.
52. Harger, M.J.P. Chemical Shift Non-equivalence of Enantiomers in the Proton Magnetic Resonance Spectra of Partly Resolved Phosphinothioic Acids. J. Chem. Soc., Perkin Trans. 2 1978, 326-331.
53. th International Conference on the Chemistry of Organic Solid State, Sestri Levante, Italy, 14-19 June 2009.