Crystal polymorphism in pendimethalin herbicide is driven by electronic delocalization and changes in intramolecular hydrogen bonding. A crystallographic, spectroscopic and computational study

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 9, 1998, Pages 2061-2071

  Stockton, Gerald W ^a   Godfrey, Russell ^b   Hitchcock, Peter ^c   Mendelsohn, Richard ^d   Mowery, Patrick C ^a   Rajan, Srinivasan ^a   Walker, Anthony F ^e  

^a PFIZER INC   (United States)

^b Pharmaceutical Sciences   (United Kingdom)

^c UNIVERSITY OF SUSSEX   (United Kingdom)

^d RUTGERS UNIVERSITY   (United States)

^e Cyanamid Agriculture Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000844380     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a705178f     Document Type: Article

References (66)

1. G. R. Desiraju, Science, 1997, 278, 404.
2. A. S. Meyerson, Handbook of Industrial Crystallization, Butterworth-Heinemann Series in Chemical Engineering, ed. H. Brenner, Butterworth-Heinemann, Boston, 1993.
3. T. L. Therlfall, Analyst, 1995, 120, 2435.
4. G. Clydesdale, K. J. Roberts, K. Lewtas and R. Docherty, J. Cryst. Growth, 1994, 141, 443.
5. R. J. Davey, J. Cryst. Growth, 1975, 29, 212.
6. R. J. Davey, J. Cryst. Growth, 1976, 34, 109.
7. Z. Berkovitch-Yellin, J. Am. Chem. Soc., 1985, 107, 3111.
8. Y. Weisinger-Lewiz, F. Frolow, R. K. McMullan, T. F. Koetzle, M. Lahav and L. Leiserowitz, J. Am. Chem. Soc., 1989, 111, 1035.
9. H. W. Karfunkel, F. J. J. Leusen and R. J. Gdanitz, J. Comput.-Aided Mater. Des., 1993, 1, 177.
10. K. T. Thomson, R. M. Wentzcovitch and M. S. T. Bukowinski, Science, 1996, 274, 1880.
11. G. Clydesdale, K. J. Roberts and R. Docherty, J. Cryst. Growth, 1996, 166, 78.
12. R. Docherty, G. Clydesdale, K. J. Roberts and P. Bennema, J. Phys. D: Appl. Phys., 1991, 24, 88.
13. M. H. J. Hottehuis, J. G. E. Gardeniers, L. Jetten and P. Bennema, J. Cryst. Growth, 1988, 92, 171.
14. P. Hartman and P. Bennema, J. Cryst. Growth, 1980, 49, 145.
15. P. Hartman, J. Cryst. Growth, 1980, 49, 157.
16. J. D. H. Donnay and D. Harker, Am. Mineral., 1937, 22, 446.
17. W. T. M. Mooij, B. O. van Eijck, S. L. Price, P. Verwer and J. Kroon, J. Comput. Chem., 1998, 19, 459.
18. A. Gavezotti, Acc. Chem. Res., 1994, 27, 309.
19. A. Gavezotti, Curr. Opin. Solid State Mater. Sci., 1996, 1, 501.
20. G. Clydesdale and K. J. Roberts, Langmuir, 1996, 12, 5722.
21. P. L. Sprankle, Proc. Br. Weed Control Conf., 12th, 1974, 2, 825.
22. The Pesticide Manual incorporating the Agrochemicals Handbook, British Crop Protection Council, Surrey, UK, and The Royal Society of Chemistry, London, UK, 10th edn., 1994.
23. F. L. Ashton and A. S. Crofts, Mode of Action of Herbicides., Wiley, New York, 1981.
24. Solid/Liquid Dispersions, ed. Th. F. Tadros, Academic Press, New York, 1987.
25. The work described in this paper aided the development of a physically stable suspension concentrate formulation for pendimethalin, as described by L. J. Morgan and M. Bell, US Patent No. 4 871 392, October 3, 1989, and L. J. Morgan, US Patent No. 4 875 929, October 24, 1989.
26. The work described in this paper aided the development of a physically stable suspension concentrate formulation for pendimethalin, as described by L. J. Morgan and M. Bell, US Patent No. 4 871 392, October 3, 1989, and L. J. Morgan, US Patent No. 4 875 929, October 24, 1989.
27. G. Germain, P. Main and M. M. Woolfson, Acta Crystallogr., Sect. B, 1970, 26, 91.
28. E. R. Andrew, A. Bradbury and R. G. Eades, Nature, 1958, 182, 1659.
29. B. Schneider, D. Doskocilova, J. Babka and Z. Ruzicka, J. Magn. Reson., 1980, 37, 41.
30. W. T. Dixon, J. Schaefer, E. O. Stejskal and R. A. McKay, J. Magn. Reson., 1982, 49, 341.
31. G. Scheler, U. Haubenreisser and H. Rosenberger, J. Magn. Reson., 1981, 44, 134.
32. W. Kiefer and H. J. Bernstein, Appl. Spectrosc., 1971, 25, 609.
33. SYBYL Molecular Modeling Software, version 5.2 is a product of Tripos Associates, Inc, a Subsidiary of Evans and Sutherland, 1699 S. Hanley Rd., Suite 303, St. Louis, Missouri 63144.
34. CERIUS Crystal Modeling Software, Molecular Simulations Inc, Burlington, Massachusetts.
35. S. L. Mayo, W. A. Godard III and B. D. Olafson, J. Phys. Chem., 1990, 94, 8897.
36. J. E. Ridley and M. C. Zerner, Theor. Chim. Acta., 1973, 32, 111.
37. M. C. Zerner, G. H. Loew, R. F. Kirchner and U. T. Mueller-Westerhoff, J. Am. Chem. Soc., 1980, 102, 589.
38. W. D. Edwards, B. Weiner and M. C. Zerner, J. Am. Chem. Soc., 1986, 108, 2196.
39. J. Bernstein and A. T. Hagler, J. Am. Chem. Soc., 1978, 100, 673.
40. A. T. Hagler and J. Bernstein, J. Am. Chem. Soc. 1978, 100, 6349.
41. J. Bernstein, Acta Crystallogr., Sect. B, 1979, 35, 360.
42. A Warshel and S. Lifson, J. Chem. Phys., 1970, 53, 582.
43. R. M. Wentzcovitch, Phys. Rev. B: Condens. Matter, 1991, 44, 2358.
44. R. M. Wentzcovitch, J. L. Martins and G. D. Price, Phys. Rev. Lett., 1993, 70, 3947.
45. A. Guvezotti, NATO ASI Ser., Ser. C, 1994, 426, 51.
46. R. K. Hester, J. L. Ackerman, J. L. Neff and J. S. Waugh, Phys. Rev. Lett., 1976, 36, 1081.
47. A. Pines, M. G. Gibby and J. S. Waugh, J. Chem. Phys., 1973, 59, 569.
48. J. Schaefer and E. O. Stejskal, J. Am. Chem. Soc., 1976, 98, 1031.
49. C. A. Fife, Solid State NMR for Chemists, CFC Press, Guelf, Ontario, Canada, 1983.
50. J. A. Ripmeester, Chem. Phys. Lett., 1980, 536.
51. C. Doherty and P. York, Int. J. Pharm., 1988, 47, 141.
52. J. G. Hexam, M. H. Frey and S. J. Opella, J. Chem. Phys., 1982, 77, 3847.
53. The Aldrich Library of NMR Spectra, Pouchert and Campbell, 1974.
54. J. C. Bellows and F. P. Chen, Drug Dev. Ind. Pharm., 1977, 3, 451.
55. K. Kumar and P. Carey, J. Chem. Phys., 1975, 63, 3697.
56. S. F. Mason, Q. Rev. Chem. Soc., 1961, 15, 287.
57. R. W. H. Berry, Chem. Br., 1987, 23, 210.
58. A. S. Davydov, Theory of Molecular Excitons, McGraw-Hill, New York, 1962.
59. Light and Organic Crystals, Th. Förster, in Modern Quantum Chemistry, ed. O. Sinanoglu, Academic Press, New York, 1965. pp. 93-137.
60. S. F. Mason, Q. Rev. Chem. Soc., 1963, 17, 20.
61. W. Kauzman, Quantum Chemistry, Academic Press, New York, 1957.
62. J. D. Bernal and R. H. Fowler, J. Chem. Phys., 1933, 1, 515.
63. J. A. Pople, Proc. R. Soc. London, Ser. A, 1951, 205, 163.
64. W. G. Schneider, J. Chem. Phys., 1955, 23, 26.
65. J. C. M. van Duijneveldt-van de Rijdt and F. B. van Duijneveldt, J. Am. Chem. Soc., 1971, 93, 5644.
66. S. P. Srivastara, J. Handoo, K. M. Agrawal and G. C. Joshi, J. Phys. Chem. Solids, 1993, 54, 639.