Surface-mediated nucleation in the solid-state polymorph transformation of terephthalic acid

Journal of the American Chemical Society

Volumn 129, Issue 15, 2007, Pages 4714-4723

  Beckham, Gregg T ^a   Peters, Baron ^a,c   Starbuck, Cíndy ^b   Varíankaval, Narayan ^b   Trout, Bernhardt L ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c UNIVERSITÉ DE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

APPROXIMATION THEORY; MAXIMUM LIKELIHOOD; NUCLEATION; POLYMORPHISM; PROBABILITY; SUPRAMOLECULAR CHEMISTRY;

CRYSTAL EDGES; POLYMORPH TRANSFORMATION; SUPRAMOLECULAR SYNTHONS; SURFACE-MEDIATED NUCLEATION;

SOLID STATE REACTIONS;

PHTHALIC ACID DERIVATIVE; TEREPHTHALIC ACID;

ARTICLE; CRYSTAL STRUCTURE; MOLECULAR MECHANICS; MOLECULAR MODEL; SOLID STATE; STATISTICAL MODEL; SUPRAMOLECULAR CHEMISTRY; SURFACE PROPERTY;

CRYSTALLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHTHALIC ACIDS; PROBABILITY;

EID: 34247490604     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0687567     Document Type: Article

References (54)

1. Mullin, J. W. Ctystallization, 4th ed.; Butterworth-Heinemann: Oxford, 2001.
2. Matsui, M.; Price, G. D. Nature 1991, 351, 735-737.
3. Eddaoudi, M.; Kim, J.; Rosi, N.; Vodak, D.; Wachter, J.; O'Keefe, M.; Yaghi, O. M. Science 2002, 295, 469-472.
4. Sawada, K. Pure Appl. Chem. 1997, 69, 921-928.
5. Spanos, N.; Koutsoukos, P. G. J. Cryst. Growth 1998, 191, 783-790.
6. Irie, M.; Kobatake, S.; Horichi, M. Science 2001, 291, 1769-1772.
7. Morris, K. R.; Griesser, U. J.; Eckhardt, C. J.; Stowell, J. G. Adv. Drug Delivery Rev. 2001, 48, 91-114.
8. Vippagunta, S. R.; Brittain, H. G.; Grant, D. J. W. Adv. Drug Delivery Rev. 2001, 48, 3-26.
9. Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658.
10. Yu, L. X.; Furness, M. S.; Raw, A.; Outlaw, K. P. W.; Nashed, N. E.; Ramos, E.; Miller, S. P. F.; Adams, R. C.; Fang, F.; Patel, R. M.; Holcombe, F. O., Jr.; Chiu, Y.; Hussain, A. S. Pharm. Res. 2003, 20, 531-536.
11. Caira, M. Top. Curr. Chem. 1998, 198, 163-208.
12. Morissette, S. L.; Soukasene, S.; Levinson, D.; Cima, M. J.; Almarsson, Ö. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 2180-2184.
13. Mnyukh, Y. Fundamentals of Solid-State Phase Transitions Ferromagnetism and Ferroelectricity, 1st ed.; Springer: New York, 1998.
14. Mnyukh, Y. V. J. Cryst. Growth 1996, 32, 371-377.
15. Mnyukh, Y. V. Mol. Cryst. Liq. Cryst. 1979, 52, 163-200.
16. Mnyukh, Y. V. Mol. Cryst. Liq. Cryst. 1979, 52, 201-218.
17. Candew, P. T.; Davey, R. J.; Ruddick, A. J. J Chem. Soc. Faraday Trans. 1984, 80, 659-668.
18. Tuble, S. C.; Anwar, J.; Gale, J. D. J. Am. Chem. Soc. 2004, 26, 396-405.
19. Kaneko, F.; Yano, J.; Tsujiuchi, H.; Tashiro, K.; Suzuki, M. J. Phys. Chem. B 1998, 102, 327-330.
20. Peters, B.; Trout, B. L. J. Chem. Phys. 2006, 125, 054108.
21. Bailey, M.; Brown, C. J. Acta Cryst. 1967, 22, 387-391.
22. Sledź, M.; Janczak, J.; Kubiak, R. J. Mol. Struct. 2001, 595, 77-82.
23. Davey, R. J.; Maginn, S. J.; Andrews, S. J.; Buckley, A. M.; Cottier, D.; Dempsey, P.; Rout, J. E.; Stanley, D. R.; Taylor, A. Nature 1993, 366, 248-250.
24. Davey, R. J.; Maginn, S. J.; Andrews, S. J.; Black, S. N.; Buckley, A. M.; Cottier, D.; Dempsey, P.; Plowman, R.; Rout, J. E.; Stanley, D. R.; Taylor, A. J. Chem. Soc. Faraday Traits. 1994, 90, 1003-1009.
25. Moroni, D.; ten Wolde, P. R.; Bolhuis, P. G. Phys. Rev. Lett. 2005, 94, 235703.
26. Zahn, D. Phys. Rev. Lett. 2004, 92, 040801.
27. Radhakrishnan, R.; Trout, B. L. J. Am. Chem. Soc. 2003, 125, 7743-7747.
28. Dellago, C.; Bolhuis, P. G.; Geissler, P. L. Adv. Chem. Phys. 2002, 123, 1-86.
29. Dellago, C.; Bolhuis, P. G.; Csajka, F. S.; Chandler, D. J. Chem. Phys. 1998, 108, 1964-1977.
30. Dellago, C.; Bolhuis, P. G.; Chandler, D. J. Chem. Phys. 1998, 108, 9236-9245.
31. Bolhius, P. G.; Dellago, C.; Chandler, D. Faraday Discuss. 1998, 110, 421-436.
32. Chu, J. W.; Brooks, B. R.; Trout, B. L. J. Am. Chem. Soc. 2004, 126, 16601-16607.
33. Steinhardt, P. J.; Nelson, D. R.; Ronchetti, M. Phys. Rev. B 1983, 28, 784-805.
34. Radhakrishuan, R.; Trout, B. L. J. Chem. Phys. 2002, 117, 1786-1796.
35. Ma, A.; Dinner, A. R. J. Phys. Chem. B 2005, 109, 6769-6779.
36. Best, R. B.; Hummer, G. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 6732-6737.
37. Maragliano, L.; Fischer, A.; Vanden-Eijnden, E.; Ciccotti, G. J. Chem. Phys. 2006, 125, 024106.
38. Du, R.; Pande, V. S.; Grosberg, A. Y.; Tanaka, T.; Shakhnovich, E. S. J. Chem. Phys. 1998, 108, 334-350.
39. Geissler, P. L.; Dellago, C.; Chandler, D. J. Phys. Chem. B 1999, 103, 3706-3710.
40. Truhlar, D. G.; Garrett, B. C. J. Phys. Chem. B 2000, 104, 1069-1072.
41. Desiraju, G. R. Angew. Chem., Int. Ed. 1995, 34, 2311-2327.
42. Ryckaert, J.; Ciccotti, G.; Berendsen, H. J. Comput. Phys. 1977, 23, 327-341.
43. Gavezzotti, A.; Fillippini, G. J. Phys. Chem. 1994, 98, 4831-4837.
44. Raabe, G. Z. Naturforsch., A: Phys. Sci. 2002, 57a, 961-966.
45. MacKerell, A. D.; Wiórkiewicz-Kuczera, J.; Karplus, M. J. Am. Chem. Soc. 1995, 117, 11946-11975.
46. Frisch, M. J.; et al. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
47. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
48. Besler, B. H.; Merz, K. M.; Kollman, P. A. J. Comput. Chem. 1990, 11, 431-439.
49. Singh, U. C.; Kollman, P. A. J. Comput. Chem. 1984, 5, 129-145.
50. Breneman, C. M.; Wilberg, K. B. J. Comput. Chem. 1990, 11, 361-373.
51. Kottalam, J.; Case, D. A. J. Am. Chem. Soc. 1988, 110, 7690-7697.
52. Radhakrishnan, R.; Schlick, T. J. Chem. Phys. 2004, 121, 2436-2444.
53. Turnbull, D.; Fisher, J. C. J. Chem. Phys. 1949, 17, 71-73.
54. It should be noted that after this manuscript was accepted, a study by Anwar, J.; Tuble, S. C.; Kendrick, J. J. Am. Chem. Soc. 2007, 9, 2542-2547 was published which shows concerted molecular displacements in a periodic system of DL-norleucine crystals using molecular dynamics techniques.