Kinetics and thermodynamics of efficient chiral symmetry breaking in nearly racemic mixtures of conglomerate crystals

Crystal Growth and Design

Volumn 11, Issue 5, 2011, Pages 1957-1965

  Skrdla, Peter J ^a  

^a NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL SYMMETRY; DISPERSIVE KINETICS; FIRST-ORDER; HOMOCHIRALITY; KINETICS AND THERMODYNAMICS; PHASE TRANSFORMATION; RACEMIC MIXTURES; SECONDARY NUCLEATION; SOLUTION PHASE;

CRYSTALS; NUCLEATION; OSTWALD RIPENING; POWER QUALITY; THERMODYNAMICS;

CRYSTAL SYMMETRY;

EID: 79957930576     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg200116e     Document Type: Article

References (70)

1. Viedma, C. Phys. Rev. Lett. 2005, 94, 065504.
2. Viedma, C. Astrobiology 2007, 7, 312.
3. Uwaha, M. J. Phys. Soc. Jpn. 2004, 73, 2601.
4. Noorduin, W. L.; Izumi, T.; Millemaggi, A.; Leeman, M.; Meekes, H.; Van Enckevort, W. J. P.; Kellogg, R. M.; Kaptein, B.; Vlieg, E.; Blackmond, D. G. J. Am. Chem. Soc. 2008, 130, 1158.
5. Viedma, C.; Ortiz, J. E.; de Torres, T.; Izumi, T.; Blackmond, D. G. J. Am. Chem. Soc. 2008, 130, 15274.
6. Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767.
7. Noorduin, W. L.; van der Asdonk, P.; Bode, A. A. C; Meekes, H.; van Enckevort, W. J. P.; Vlieg, E.; Kaptein, B.; van der Meijden, M. W.; Kellogg, R. M.; Deroover, G. Org. Process. Res. Dev. 2010, 14, 908.
8. Skrdla, P. J. J. Phys. Chem. A 2009, 113, 9329.
9. Pasteur, L. C. Hebd. Séanc. Acad. Sci. Paris 1848, 26, 535.
10. Allenmark, S.; Schurig, V. J. Mater. Chem. 1997, 7, 1955.
11. Kaemmerer, H.; Lorenz, H.; Black, S. N.; Seidel-Morgenstern, A Cryst. Growth Des. 2009, 9, 1851.
12. In those ∼85% of cases, the handedness of the molecules does not appear to affect their ability to interact with each other in the crystal packing arrangement.
13. Kondepudi, D. K; Kaufman, R. J.; Singh, N. Science 1990, 250, 975.
14. Kondepudi, D. K; Bullock, K. L.; Digits, J. A; Yarborough, P. D. J. Am. Chem. Soc. 1995, 117, 401.
15. Kondepudi, D. K; Asakura, K Acc. Chem. Res. 2001, 34, 946.
16. Kipping, F. S.; Pope, W. J. Nature 1898, 59, 53.
17. The rate-limiting step of a multistep/complex process defines the critical mechanism responsible for producing the observed kinetics.
18. Frank, F. C. Biochim. Biophys. Acta 1953, 11, 459.
19. Cartwright, J. H. E.; García-Ruiz, J. M.; Piro, O.; Sainz-Díaz, C. I.; Tuval, I. Phys. Rev. Lett. 2004, 93, 035502.
20. McBride, J. M.; Carter, R. L. Angew. Chem, Int. Ed. 1991, 30, 293.
21. Qian, R.-Y.; Botsaris, D. Chem. Eng. Sci. 1998, 53, 1745.
22. Ostwald, W. Z. Phys. Chem. 1907, 34, 295.
23. McBride, J. M.; Tully, J. C. Nature 2008, 452, 161.
24. Plasson, R.; Brandenburg, A. Chirality 2010, 40, 93.
25. Noorduin, W. L.; Meekes, H.; Bode, A. A. C.; van Enckevort, W. J. P.; Kaptein, B.; Kellogg, R. M.; Vlieg, E. Cryst. Growth Des. 2008, 8, 1675.
26. Viedma, C.; Verkuijl, B. J. V.; Ortiz, J. E.; de Torres, T.; Kellogg, R. M.; Blackmond, D. G Chem.-Eur. J. 2010, 16, 4932.
27. Noorduin, W. L.; van Enckevort, W. J. P.; Meekes, H.; Kaptein, B.; Kellogg, R. M.; Tully, J. C.; McBride, J. M.; Vlieg, E. Angew. Chem., Int. Ed. 2010, 49, 8435.
28. Uwaha, M.; Katsuno, H. J. Phys. Soc. Jpn. 2009, 78, 023601.
29. Cartwright, J. H. E.; Piro, O.; Tuval, I. Phys. Rev. Lett. 2007, 98, 165501.
30. Bonner, W. A. Orig. Life Evol. Biosphere 1991, 21, 59.
31. Plonka, A. Annu. Rep. Prog. Chem., Sect. C 2001, 97, 91.
32. Plonka, A. Annu. Rep. Prog. Chem., Sect. C 1988, 85, 47.
33. Adding a small amount of one dissolved enantiomer to the solution phase triggers the process to evolve in favor of the opposite chirality ("a small initial enantiomeric excess...may be induced by minute amounts of chiral species present in the solution"). In contrast, a starting excess of crystals of a particular enantiomer should drive the enrichment toward the same handedness (in the solid-state), due to the increased probability of secondary nucleation on that phase. In either case, the imbalance perturbs the system chemical potential, thus providing the initial driving force for the enantioenrichment.
34. Lifshitz, I. M.; Slyozov, V. V J. Phys. Chem. Solids 1961, 19, 35.
35. Wagner, C. Z. Elektrochem. 1961, 65, 581.
36. Saito, Y.; Hyuga, H. J. Phys. Soc. Jpn. 2008, 77, 113001.
37. Blackmond, D. G Angew. Chem., Int. Ed. 2009, 48, 2648.
38. Lente, G. J. Math. Chem. 2010, 47, 1106.
39. While the arguments presented in ref 37 have merit for most homogeneous reactions monitored on the macroscopic scale, if there were no out-of-equilibrium relaxation effects (e.g., molecular dynamics, observed on the microscopic level), which impart heterogeneity to the 8, 31, 32 system, then one would not observe dispersive kinetics in nature.
40. Volmer, M.; Weber, A. Z. Phys. Chem. 1926, 119, 227.
41. Becker, R; Döring, W. Ann. Phys. 1935, 24, 719.
42. Madras, G; McCoy, B. J. J. Colloid Interface Sci. 2003, 261, 423.
43. Bronnikov, S.; Dierking, I. Physica B 2005, 358, 339.
44. 26 seems valid only if the dissolution/recrystallization is sufficiently rapid such that the solids serve solely as "molecular reservoirs" for the solution phase racemization.
45. Johnson, W. A.; Mehl, R. F. Trans. AIME 1939, 135, 416.
46. Avrami, M. J. Chem. Phys. 1939, 7, 1103.
47. Avrami, M. J. Chem. Phys. 1940, 8, 212.
48. Avrami, M. J. Chem. Phys. 1941, 9, 177.
49. Erofe'ev, B. V. Dokl. Akad. Nauk SSSR 1946, 52, 511.
50. Kolmogorov, A. N. Izv. Akad. Nauk. SSSR 1937, 1, 355.
51. Khawam, A.; Flannagan, D. R. J. Phys. Chem. B 2006, 110, 17315.
52. Bednarek, J.; Plonka, A.; Pacewska, B.; Pysiak, J. Thermochim. Acta 1996, 282/283, 51.
53. Sun, N. X.; Liu, X. D.; Lu, K. Scripta Metall. 1996, 34, 1201.
54. Onischuk, A. A.; Purtov, P. A.; Baklanov, A. M.; Karasev, V. V.; Vosel, S. V. J. Chem. Phys. 2006, 124, 014506.
55. Furthermore, eq 8 in ref 26 results in a "catastrophe" as t → ∞; eq 2/eq 6 in this manuscript do not.
56. Shields, S. P.; Richards, V. N.; Buhro, W. E. Chem. Mater. 2010, 22, 3212.
57. Zheng, H.; Smith, R. K.; Jun, Y.-W.; Kisielowski, C.; Dahmen, U.; Alivisatos, A. P. Science 2009, 324, 1309.
58. Anwar, J.; Boateng, P. K. J. Am. Chem. Soc. 1998, 120, 9600.
59. Hamad, S.; Moon, C.; Catlow, C. R. A.; Hulme, A. T.; Price, S. L. J. Phys. Chem. B 2006, 110, 3323.
60. Bogush, G. H.; Zukowski, C. F. J. Colloid Interface Sci. 1991, 142, 19.
61. De Smet, Y.; Deriemaeker, L.; Parloo, E.; Finsy, R. Langmuir 1999, 15, 2327.
62. In ref 56, the PSDs were modeled using a Gaussian distribution that likely does not support any single rate-limiting mechanism.
63. Skrdla, P. J. Chem. Mater. 2010, 22, 2685.
64. Vyazovkin, S.; Wight, C. A. Thermochim. Acta 1999, 53, 340.
65. Rousseau, R. W.; O'Dell, F. P. Ind. Eng. Chem. Process Des. Dev. 1980, 19, 603.
66. Mitchell, C. A.; Yu, L.; Ward, M. D. J. Am. Chem. Soc. 2001, 123, 10830.
67. Cox, J. R.; Ferris, L. A.; Thalladi, V. R. Angew. Chem., Int. Ed. 2007, 46, 4333.
68. Skrdla, P. J. Phys. Chem. Chem. Phys. 2010, 12, 3788.
69. Skrdla, P. J. J. Pharm. Biomed. Anal. 2007, 45, 251.
70. Meyerhoffer, W. Ber. Dtsch. Chem. Ges. 1904, 37, 2604.