Metastability in supersaturated solution and transition towards chirality in the crystallization of NaClO3

Angewandte Chemie - International Edition

Volumn 50, Issue 10, 2011, Pages 2359-2363

  El Hachemi, Zoubir ^a   Crusats, Joaquim ^a   Ribó, Josep M ^a   McBride, J Michael ^b   Veintemillas Verdaguer, Sabino ^c  

^a UNIVERSITY OF BARCELONA   (Spain)

^b YALE UNIVERSITY   (United States)

^c CENTRO DE ASTROBIOLOGÍA CSIC INTA   (Spain)

Author keywords

Autocatalysis; Chirality; Crystal growth; Phase transitions; Racemic conglomerates

Indexed keywords

AUTOCATALYSIS; CRYSTAL MIXTURES; HOMOCHIRAL; METASTABILITIES; RACEMIC CONGLOMERATES; SUPERSATURATED SOLUTIONS; SYMMETRY-BREAKING;

CHIRALITY; CRYSTAL GROWTH; CRYSTALLIZATION; ENANTIOMERS; STEREOCHEMISTRY;

PHASE TRANSITIONS;

CHLORIDE; CHLORITE; WATER;

ARTICLE; CHEMISTRY; CRYSTALLIZATION; PHASE TRANSITION; SOLUTION AND SOLUBILITY; STEREOISOMERISM;

CHLORIDES; CRYSTALLIZATION; PHASE TRANSITION; SOLUTIONS; STEREOISOMERISM; WATER;

EID: 79952055261     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201007209     Document Type: Article

References (53)

1. a) C. Viedma, Phys. Rev. Lett. 2005, 94, 065504;
2. b) C. Viedma, Cryst. Growth Des. 2007, 7, 553-556;
3. c) W. L. Noorduin, T. Izumi, A. Millemaggi, M. Leeman, H. Meekens, W. J. P. van Enckevort, R. M. Kellogg, B. Kaptein, E. Vlieg, D. G. Blackmond, J. Am. Chem. Soc. 2008, 130, 1158-1159;
4. d) B. Kaptein, W. L. Noorduin, H. Meekes, W. J. P. van Enckvort, R. M. Kellogg, E. Vlieg, Angew. Chem. 2008, 120, 7336-7339;
5. Angew. Chem. Int. Ed. 2008, 47, 7226-7229;
6. e) C. Viedma, J. E. Ortiz, T. de Torres, T. Izumi, D. G. Blackmond, J. Am. Chem. Soc. 2008, 130, 15274-15275;
7. f) W. K. Rybak, Tetrahedron: Asymmetry 2008, 19, 2234-2239;
8. g) S. B. Tsogoeva, S. Wei, M. Mauksch, Angew. Chem. 2009, 121, 598-602;
9. Angew. Chem. Int. Ed. 2009, 48, 590-594;
10. h) M. P. S. Cheung, L. A. Cuccia, Chem. Commun. 2009, 1337-1338;
11. G. Levilain, C. Rougeot, F. Guillen, J.-C. Plaquevent, G. Cocquerel, Tetrahedron: Asymmetry 2009, 20, 2769-2771;
12. j) W. L. Noorduin, P. van der Asdonk, H. Meekes, W. J. P. van Enckervort, B. Kaptein, M. Leeman, R. M. Kellogg, E. Vlieg, Angew. Chem. 2009, 121, 3328-3330;
13. Angew. Chem. Int. Ed. 2009, 48, 3278-3280;
14. k) S. Wei, M. Mauksch, S. B. Tsogoeva, Chem. Eur. J. 2009, 15, 10255-10262;
15. l) A. Flock, C. M. M. Reucher, C. Bolm, Chem. Eur. J. 2010, 16, 3918-3921;
16. m) W. L. Noorduin, H. Meekes, W. J. P. van Enckevort, B. Kaptein, R. M. Kellogg, E. Vlieg, Angew. Chem. 2010, 122, 2593-2595;
17. Angew. Chem. Int. Ed. 2010, 49, 2539-2541.
18. R. Plasson, D. K. Kondepudi, H. Bersini, A. Commeyras, K. Asakura, Chirality 2007, 19, 589-600.
19. J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates and Resolutions, Wiley, New York, 1981, pp. 35-36.
20. R. S. Ward, Tetrahedron: Asymmetry 1995, 6, 1475-1490.
21. D. Zbaida, M. Lahav, K. Dranz, G. Knaup, M. Kottenhahn, Tetrahedron 2000, 56, 6645-6649.
22. a) D. L. Kondepudi, R. Kaufman, N. Singh, Science 1990, 250, 975-977;
23. b) D. L. Kondepudi, K. L. Bullock, J. A. J. A. Digits, J. K. Hall, J. M. Miller, J. Am. Chem. Soc. 1993, 115, 10211-10216;
24. c) D. L. Kondepudi, K. L. Bullock, J. A. Digits, P. D. Yarborough, J. Am. Chem. Soc. 1995, 117, 401-404;
25. d) B. Martin, A. Tharrington, X-I. Wu, Phys. Rev. Lett. 1996, 77, 2826-2829;
26. e) D. K. Kondepudi, J. Laudadio, K. Asakura, J. Am. Chem. Soc. 1999, 121, 1448-1451.
27. a) J. M. McBride, R. L. Carter, Angew. Chem. 1991, 103, 298-300;
28. Angew. Chem. Int. Ed. Engl. 1991, 30, 293-295;
29. b) K. Asakura, T. Soga, T. Uchida, S. Osanai, D. L. Kondepudi, Chirality 2002, 14, 85-89;
30. c) H. E. Cartwright, J. M. Garcia-Ruiz, O. Piro, C. I. Sainz-Diaz, I. Tuval, Phys. Rev. Lett. 2004, 93, 035502.
31. Z. El-Hachemi, J. Crusats, J. M. Ribo, S. Veintemillas-Verdaguer, Cryst. Growth Des. 2009, 9, 4802-4806.
32. a) M. Uwaha, J. Phys. Soc. Jpn. 2004, 73, 2601-2603;
33. R. Plasson, D. K. Kondepudi, K. Asakura, J. Phys. Chem. B 2006, 110, 8481-8487;
34. b) C. Viedma, Astrobiology 2007, 7, 312-319;
35. c) D. G. Blackmond, Chem. Eur. J. 2007, 13, 3290-3295;
36. d) J. H. E. Cartwright, O. Piro, I. Tuval, Phys. Rev. Lett. 2007, 98, 165501;
37. e) L. W. Noorduin, H. Meekes, A. A. C. Bode, W. J. P. van Enckevort, B. Kaptein, R. M. Kellogg, E. Vlieg, Cryst. Growth Des. 2008, 8, 1675-1681;
38. f) J. M. McBride, J. C. Tully, Nature 2008, 452, 161-162;
39. g) M. Uwaha, J. Phys. Soc. Jpn. 2008, 77, 083802;
40. h)W. L. Noorduin, H. Meekes, W. J. P. van Enkevort, A. Millemaggi, M. Leeman, B. Kaptein, R. M. Kellogg, E. Vlieg, Angew. Chem. 2008, 120, 6545-6547;
41. Angew. Chem. Int. Ed. 2008, 47, 6445-6447;
42. i) Y. Saito, H. Hyuga, J. Phys. Soc. Jpn. 2008, 77, 113001;
43. j) H. Katsuno, M. Uwaha, J. Cryst. Growth 2009, 311, 4265-4269;
44. k) Y. Saito, H. Hyuga, J. Phys. Soc. Jpn. 2009, 78, 104001.
45. J. Crusats, S. Veintemillas-Verdaguer, J. M. Ribo, Chem. Eur. J. 2006, 12, 7776-7781.
46. J. H. van't Hoff, Ber. Dtsch. Chem. Ges. 1902, 35, 4252-4264.
47. R. K. Freier, Aqueous Solutions: Data for Inorganic and Organic Compounds, Vol. 1, W. de Gruyter, Berlin, 1976.
48. The opening at the end of the experiment of one of the ground-glass joints allows the top of the reactor with the cups to cool faster, so that crystallization may first occur in the cups (between 10 to 30 s delay).
49. W. Polak, K. Sangwal, J. Cryst. Growth 1995, 152, 182-190.
50. S. Osuna-Esteban, M. P. Zorzano, C. Menor-Salván, M. Ruiz-Bermejo, S. Veintemillas-Verdaguer, Phys. Rev. Lett. 2008, 100, 146102.
51. W. L. Noorduin, W. J. P. van Enkevort, H. Meekes, B. Kaptein, R. M. Kellogg, J. C. Tully, J. M. McBride, E. Vlieg, Angew. Chem. 2010, 122, 8613-8616;
52. Angew. Chem. Int. Ed. 2010, 49, 8435-8438.
53. L. Addadi, M. Lahav, J. Am. Chem. Soc. 1979, 101, 2152-2156.