Mechanochromism of piroxicam accompanied by intermolecular proton transfer probed by spectroscopic methods and solid-phase changes

Journal of the American Chemical Society

Volumn 127, Issue 18, 2005, Pages 6641-6651

  Sheth, Agam R ^a   Lubach, Joseph W ^b   Munson, Eric J ^b   Muller, Francis X ^c   Grant, David J W ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF KANSAS   (United States)

^c GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FOURIER TRANSFORM INFRARED SPECTROSCOPY; GRINDING (COMMINUTION); MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; STANDARDS; STRESSES; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

ANHYDRATES; NEUTRAL MOLECULES; PIROXICAM; SOLID-STATE DISORDER;

CHEMICALS;

AMPHOLYTE; PIROXICAM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIFFUSE REFLECTANCE SPECTROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MECHANICAL STRESS; MOLECULE; PROTON TRANSPORT; SOLID; TEMPERATURE; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

CRYSTALLIZATION; HYDROGEN BONDING; PIROXICAM; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; X-RAY DIFFRACTION;

EID: 18744374968     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045823t     Document Type: Article

References (86)

1. Limbach, H. H.; Hennig, J.; Kendrick, R.; Yannoni, C. S. J. Am. Chem. Soc. 1984, 106, 4059-4060.
2. Frydman, L.; Olivieri, A. C.; Diaz, L. E.; Frydman, B.; Morin, F.; Mayne, C. L.; Grant, D. M.; Adler, A. J. Am. Chem. Soc. 1988, 110, 336;
3. Frydman, L.; Olivieri, A. C.; Diaz, L. E.; Vega, S.; Kustanovic, I.; Frydman, B. J. Am. Chem. Soc. 1989 111, 7001.
4. Braun, J.; Schlabach, M.; Wehrle, B.; Matthias, K.; Vogel, E.; Limbach, H. H. J. Am. Chem. Soc. 1994, 116, 6593-6604.
5. Rumpel, H.; Limbach, H. H. J. Am. Chem. Soc. 1989, 111, 5429-5441.
6. Aguilar-Parilla, F.; Scherer, G.; Limbach, H. H.; Foces-Foces, M.; Cano, F. H.; Smith, J. A. S.; Toiron, C.; Elguero, J. J. Am. Chem. Soc. 1992, 114, 9657-9659.
7. Hoelger, C.-G.; Wehrle, B.; Benedict, H.; Limbach, H. H. J. Phys. Chem. 1994, 98, 843-851.
8. Destro, R. Chem. Phys. Lett. 1991, 181, 232-236.
9. Nowak, M. J.; Fulara, J.; Lapinski, L. J. Mol. Struct. 1988, 175, 91-96.
10. Bouas-Laurent, H.; Durr, H. Pure Appl. Chem. 2001, 73, 639-665.
11. Carpick, R. W.; Sasaki, D. Y.; Burns, A. R. Langmuir 2000, 16, 1270-1278.
12. Muller, H.; Eckhardt, C. J. Mol. Cryst. Liq. Cryst. 1978, 45, 313.
13. Monk, P. M. S.; Mortimer, R. J.; Rosseinsky, D. R. Electrochromism: Fundamentals and Applications; VCH: Weinheim, Germany, 1995.
14. Liptay, W. Angew. Chem., Int. Ed. Engl. 1969, 8, 177-188.
15. Ault, A.; Kopet, R.; Serianz, A. J. Chem. Educ. 1971, 48, 410.
16. Schonberg, A.; Elkaschef, M.; Nosseir, M.; Sidky, M. M. J. Am. Chem. Soc. 1958, 80, 6312-6315.
17. Heller, H. G.; Asiri, A. M. Tribochromic Compounds and their Applications. PCT Int. Appl. WO 94 26,729 (1994).
18. Charych, D. H.; Nagy, J. O.; Spevak, W.; Bednarski, M. D. Science 1993, 261, 585.
19. Reichert, A.; Nagy, J. O.; Spevak, W.; Charcych, D. J. Am. Chem. Soc. 1995, 117, 829-830.
20. Charych, D.; Cheng, Q.; Reichert, A.; Kuziemko, G.; Stroh, M.; Nagy, J. O.; Spevak, W.; Stevens, R. C. Chem. Biol. 1996, 3, 113-128.
21. Heller, H. G. In Photochromics for the Future Electronic Materials; Miller, L. S., Mullin, J. B., Eds.; Plenum, New York, 1991.
22. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Weinheim, Germany, 1990; pp 3, 285, 286.
23. Rohrig, U. F.; Troppmann, U.; Frank, I. Chem. Phys. 2003, 289, 381-388.
24. Tipikin, D. S. Russ. J. Phys. Chem. 2001, 75, 1720-1722.
25. Tipikin, D. S. [Translated from Zh. Fiz. Khim. 2001, 75, 1876-1879].
26. Nallicheri, R. A.; Rubner, M. F. Macromolecules 1991, 24, 517-525.
27. Tomioka, Y.; Tanaka, N.; Imazeki, S. J. Chem. Phys. 1989, 91, 5694-5700.
28. Frank, I.; Grimme, S.; Peyerimhoff, S. D. J. Phys. Chem. 1996, 100, 16187-16194.
29. Cohen, M. D.; Schmidt, G. M. J. J. Phys. Chem. 1962, 66, 2442-2446;
30. Inabe, T.; Okinawa, K.; Okamoto, H.; Mitani, T.; Murayama, Y.; Takeda, S. Mol. Cryst. Liq. Cryst. 1992, 216, 229.
31. Reetz, M. T.; Hoger, S.; Harms, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 181-183.
32. Benedict, C.; Langer, U.; Limbach, H. H.; Ogata, H.; Takeda, S. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 335-339.
33. Majerus, P. W.; Broze, G. J.; Miletich, J. P.; Tollefsen, D. M. In Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed.; Hardman, J. G.; Limbird, L. E., Eds.; New York: McGraw-Hill: New York. 1996; pp 640-641;
34. Majerus, P. W.; Broze, G. J.; Miletich, J. P.; Tollefsen, D. M. The Merck Index, 13th ed.; Merck & Co., Inc.: Whitehouse Station, NJ; 2001; p 7588.
35. Kojic-Prodic, B.; Ruzic-Toros, Z. Acta Ctystallogr. 1982, B38, 2948-2951.
36. Vrecer, F.; Vrbinc, M.; Meden, A. Int. J. Pharm. 2003, 256, 3-15.
37. Reck, G.; Dietz, G.; Laban, G.; Gunther, W.; Bannier, G.; Hohne, E. Pharmazie 1988, 43, 477-481.
38. Bordner, J.; Hammen, P. D.; Whipple, E. B. J. Am. Chem. Soc. 1989, 111, 6572-6578;
39. Hammen, P. D.; Berke, H.; Bordner, J.; Braisted, A. C.; Lombardino, J. G.; Whipple, E. B. J. Heterocycl. Chem. 1989, 26, 11-16.
40. Redenti, E.; Zanol, M.; Ventura, P.; Fronza, G.; Comotti, A.; Taddei, P.; Bertoluzza, A. Biospectroscopy 1999, 5, 243-251.
41. Santi, E.; Torre, M. H.; Kremer, E. Vib. Spectrosc. 1993, 5, 285-293.
42. Geckle, J. M.; Rescek, D. M.; Whipple, E. B. Magn. Reson. Chem. 1989, 27, 150-154.
43. Shakhtshneider, T. P. Solid State Ionics 1997, 101-103, 851-856;
44. Shakhtschneider, T. P.; Boldyrev, V. V. Mechanochemical synthesis and mechanical activation of drugs. In Boldyreva, E.; Boldyrev, V., Eds.; Reactivity of Molecular Solids; John Wiley & Sons: Ltd.: Chichester, 1999; pp 271-311.
45. Tipkin, D. S. Russ. J. Phys. Chem. 2001, 75, 1720-1723.
46. Byrn, S. R.; Curtin, D. Y.; Paul, I. C. J. Am. Chem. Soc. 1972, 94, 890-898;
47. Yang, Q. C.; Richardson, M. F.; Dunitz, J. D. J. Am. Chem. Soc. 1985, 107, 5535-5537;
48. Yang, Q.; Richardson, M. F.; Dunitz, J. D. Acta Crystallogr. 1989, B45, 312-323.
49. Yu, L.; Stephenson, G. A.; Mitchell, C. A.; Bunnell, C. A.; Snorek, S. V.; Bowyer, J. J.; Borchardt, T. B.; Stowell, J. G.; Byrn, S. R. J. Am. Chem. Soc. 2000, 122, 585-591.
50. Sheth, A. R.; Bates, S.; Muller, F. X.; Grant, D. J. W. Cryst. Growth Des. 2004, 4, 1091-1098.
51. Sheth, A. R.; Zhou, D.; Muller, F. X.; Grant, D. J. W. J. Pharm. Sci. 2004, 93, 3013-3026.
52. Crowley, K. J.; Zografi, G. J. Pharm. Sci. 2002, 91, 492-507.
53. Kortum, G. Reflectance Spectroscopy. Principles, Methods, Applications; Springer-Verlag: Berlin, 1969.
54. Wendlandt, W. W. M.; Hecht, H. G. Reflectance Spectroscopy; Interscience Publishers: New York, 1966.
55. Kubelka, P.; Munk, F. Z. Technol. Phys. 1931, 12, 593-601.
56. Kubelka, P. J. Opt. Soc. Am. 1947, 38, 448-457.
57. Brittain, H. G. Ultraviolet/Visible diffuse reflectance spectroscopy. In: Brittain, H. G., Ed.; Physical Characterization of Pharmaceutical Solids; Marcel Dekker: New York, 1995; pp 37-58.
58. Bielecki, A.; Burum, D. P. J. Magn. Reson., Ser. A 1995, 116(2), 215-220;
59. Ferguson, D. B.; Haw, J. F. Anal. Chem. 1995, 67, 3342-3348;
60. Takahashi, T.; Kawashima, H.; Sugisawa, H.; Baba, T. Solid State Nucl. Magn. Reson. 1999, 15, 119-123;
61. Mildner, T.; Ernst, H.; Freude, D. Solid State Nucl. Magn. Reson. 1995, 5, 269-271.
62. Pines, A.; Gibby, M. G.; Waugh, J. S. J. Chem. Phys. 1973, 59, 569-590;
63. Peersen, O. B.; Wu, X.; Smith, S. O. J. Magn. Reson., Ser. A 1994, 106, 127-131.
64. Dixon, W. T.; Schaefer, J.; Secfcik, M. D.; Stejskal, E. O.; McKay. R. A. J. Magn. Reson. 1982, 49, 341-345.
65. Stejskal, E. O.; Schaefer, J.; Waugh, J. S J. Magn. Reson. 1977, 28, 105-112.
66. Garner, W. E. Chemistry of the Solid State; Academic Press: New York,-1955;
67. Byrn, S. R.; Pfeiffer, R. R.; Stowell, J. G. Solid-State Chemistry of Drugs, 2nd ed.; SSCI, Inc.: West Lafayette, IN, 1999; pp 443-460.
68. Lindemann, F. A. Z. Phys. 1910, 11, 609-612.
69. Born, M.; Huang, K. Dynamical Theory of Crystal Lattices; Clarendon: Oxford, 1954.
70. Cahn, R. W.; Johnson, W. L. J. Mater. Res. 1986, 1, 724-732.
71. Fecht, H. J. Nature 1992, 356, 133-135.
72. Tse, J. S. J. Chem. Phys. 1992, 96, 5482-5487.
73. Tse, J. S.; Klein, M. L. Phys. Rev. Lett. 1987, 58, 1672-1675.
74. Colthup, N. B.; Daly, L. H.; Wiberley, S. E. Introduction to Infrared and Raman Spectroscopy, 3rd ed.; Academic Press: New York, 1990;
75. Socrates, G. Infrared and Raman Characteristic Group Frequencies, 3rd ed.; Wiley: Chichester, New York, 2001;
76. Bellamy, L. J. The Infrared Spectra of Complex Molecules, 3rd ed.; Chapman and Hall Ltd.: London, UK, 1975.
77. Takacs-Novak, K.; Kokosi, J.; Podanyi, B.; Noszal, B.; Tsai, R.-S.; Lisa, G.; Carrupt, P.-A.; Testa, B. Helv. Chem. Acta 1995, 78, 553-562.
78. Pearson, R. G.; Songstad, J. J. Am. Chem. Soc. 1967, 89, 1827-1836;
79. Pearson, R. G. J. Chem. Educ. 1968, 45, 581-587.
80. Katrusiak, A.; Katrusiak, A. Org. Lett. 2003, 5, 1903-1905.
81. The United States Pharmacopoeia XXVII (USP27/NF22, 27th rev.); The United States Pharmacopoeial Convention, Inc.: Rockville, MD, 2004.
82. Sheth, A. R.; Bates, S.; Muller, F. X.; Grant, D. J. W. Cryst. Growth Des. 2005, 5, 571-578.
83. Lorente, P.; Shenderovich, I. G.; Golubev, N. S.; Denisov, G. S.; Buntkowsky, G.; Limbach, H.-H. Magn. Reson. Chem. 2001, 39, S18-S29.
84. Urakaev, F. Kh.; Boldyrev, V. V. Inorg. Mater. 1999, 35, 302-305.
85. Urakaev, F. Kh.; Boldyrev, V. V. Translated from Neorganicheskie Mater. 1999, 35, 377-381.
86. Wehrle, B.; Limbach, H.-H. Chem. Phys. 1989, 136, 223-247.