Polymorphism of N,N′-diacetylbiuret studied by solid-state 13C and15N NMR spectroscopy, DFT calculations, and X-ray diffraction

Chemistry - A European Journal

Volumn 13, Issue 21, 2007, Pages 6139-6149

  Macholl, Sven ^a,b   Lentz, Dieter ^a   Börner, Frank ^c   Buntkowsky, Gerd ^d  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b GE HEALTHCARE   (United Kingdom)

^c FRAUNHOFER INSTITUTE FOR APPLIED POLYMER RESEARCH   (Germany)

^d FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Ab initio calculations; Hydrogen bonds; Polymorphism; Solid state NMR spectroscopy; X ray diffraction

Indexed keywords

HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMORPHISM; SOLID STATE REACTIONS; X RAY DIFFRACTION ANALYSIS;

AB INITIO CALCULATIONS; SOLID-STATE NMR SPECTROSCOPY;

COMPLEXATION;

EID: 34547140392     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601843     Document Type: Article

References (64)

1. C. B. Aakeröy, K. R. Seddon, Chem. Soc. Rev. 1993, 22, 397-407.
2. G. R. Desiraju, The Crystal As a Supramolecular Entity, Perspectives in Supramolecular Chemistry, Vol. 2, Wiley, Chichester, 1996, pp. 9-11.
3. G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449.
4. B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629-1658.
5. M. U. Schmidt, NATO ASI Ser., Ser. C 1999, 538, 331-348.
6. J. Haleblian, W McCrone, J. Pharm. Sci. 1969, 58, 911-929.
7. S. R. Vippagunta, H. G. Brittain, D. J. W. Grant, Adv. Drug Delivery Rev. 2001, 48, 3-26.
8. J. Bernstein, Polymorphism in Molecular Crystals, (International Union of Crystallography Monographs on Crystallography, Vol. 14), Oxford University Press, Oxford, 2002.
9. W. Herbst, K. Hunger, Industrial Organic Pigments, VCH, Weinheim, 1993.
10. M. U. Schmidt, R. E. Dinnebier, J. Appl. Crystallogr. 1999, 32, 178-186.
11. A. Burger, Pharm Int. 1982, 3, 158-163.
12. K. R. Morris, Drugs Pharm Sci. 1999, 95, 125-181.
13. K. D. M. Harris, M. Tremayne, Chem. Mater. 1996, 8, 2554-2570.
14. W. I. F. David, K. Shankland, N. Shankland, Chem. Commun. 1998, 931-932.
15. G. Lincke, Dyes Pigm. 2003, 59, 1-24.
16. S. Macholl, F. Borner, G. Buntkowsky, Z. Phys. Chem. (Muenchen Ger.) 2003, 217, 1473-1505.
17. S. Macholl, F. Börner, G. Buntkowsky, Chem. Eur. J. 2004, 10, 4808-4816.
18. F. Börner, Synthese, Charakterisierung und Untersuchung von schwerlöslichen Harnstoffderivaten als Grundlage für Düngemittel, PhD Thesis, FU Berlin, Berlin, 2000, p. 145.
19. A. E. Bennett, C. M. Rienstra, M. Auger, K. V. Lakshmi, R. G. Griffin, J. Chem. Phys. 1995, 103, 6951-6958
20. G. Metz, X. Wu, S. O. Smith, J. Magn. Reson., Ser. A 1994, 110, 219-227.
21. W. E. Earl, D. L. VanderHart, J. Magn. Reson. 1982, 48, 35-54.
22. S. Hayashi, Magn. Reson. Chem. 1999, 37, 843-851.
23. S. Macholl, Determination of Molecular Structures by Dipolar Solid State NMR Spectroscopy, PhD Thesis, FU Berlin, Berlin, 2002, p. 145.
24. R. M. Claramunt, D. Sanz, C. Lopez, J. A. Jimenez, M. L. Jimeno, J. Elguero, A. Fruchier, Magn. Reson. Chem. 1997, 35, 35-75.
25. Gaussian 98, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzeswski, J. A. Montgomery, R. E. Stratman, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Marin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzales, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburg, PA, 1998.
26. MATLAB, The MathWorks, Inc., Natwick, MA, 1984-2000.
27. H. Fukui, Prog. Nucl. Mag. Res. 1997, 31, 317-342.
28. K. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251-8260.
29. A. K. Jameson, C. J. Jameson, Chem. Phys. Lett. 1987, 134, 461-466.
30. SHELXS-97, Program for Crystal Structure Solution, G. M. Sheldrick, Göttingen, 1997.
31. SHELXL-97, Program for Crystal Structure Refinement, G. M. Sheldrick, Göttingen, 1997.
32. M. Bak, J. T. Rasmussen, N. C. Nielsen, J. Magn. Reson. 2000, 147, 296-330.
33. G. Eden, Y. K. Lee, M. H. Levitt, J. Magn. Reson. Ser. A 1996, 120, 56-71.
34. M. Hohwy, H. Bildsoe, H. J. Jakobsen, N. C. Nielsen, J. Magn. Reson. 1999, 136, 6-14.
35. M. H. Levitt, G. Eden, Mol. Phys. 1998, 95, 879-890.
36. T. Charpentier, C. Fermon, J. Virlet, J. Magn. Reson. 1998, 132, 181-190.
37. M. Bak, N. C. Nielsen, J. Magn. Reson. 1997, 125, 132-139.
38. W. H. Press, B. P. Flannery, S. A. Teukolsky, W. T. Wetterling, Numerical Recipes, Cambridge University Press, Cambridge, 1986.
39. S.-F. Liu, J.-D. Mao, J. Magn. Reson. 2002, 155, 15-28.
40. T. Gullion, J. Schaefer, Adv. Magn. Reson. 1989, 14, 57-83.
41. T. Gullion, J. Schaefer, J. Magn. Reson. 1989, 81, 196-200.
42. I. Sack, S. Macholl, J. H. Fuhrhop, G. Buntkowsky, Phys. Chem. Chem. Phys. 2000, 2, 1781-1788.
43. M. Strohmeier, A. M. Orendt, D. W. Alderman, D. M. Grant, J. Am. Chem. Soc. 2001, 123, 1713-1722.
44. K. Damodaran, G. J. Sanjayan, P. R. Rajamohanan, S. Ganapathy, K. N. Ganesh, Org. Lett. 2001, 3, 1921-1924.
45. M. D. Lumsden, R. E. Wasylishen, K. Eichele, M. Schindler, G. H. Penner, W. P. Power, R. D. Curtis, J. Am. Chem. Soc. 1994, 116, 1403-1413.
46. G. Buntkowsky, I. Sack, H.-H. Limbach, B. Kling, J. Fuhrhop, J. Phys. Chem. B 1997, 101, 11265-11272.
47. W. L. Jarrett, C. G. Johnson, L. J. Mathias, J. Magn. Reson. Ser. A 1995, 116, 156-160.
48. B. Testa, Principles of Organic Stereochemistry, Marcel Dekker, New York, 1979.
49. G. A. Jeffrey, L. Lewis, Carbohydr. Res. 1978, 60, 179-182.
50. R. Taylor, O. Kennard, Acta Crystallogr. Sect. B 1983, 39, 133-138.
51. T. Steiner, Cryst. Rev. 2003, 9, 177-228.
52. T. Steiner, Angew. Chem. 2002, 114, 50-80;
53. Angew. Chem. Int. Ed. 2002, 41, 48-76.
54. Z. Berkovitch-Yellin, L. Leiserowitz, Acta Crystallogr. Sect. B 1984, 40, 159-165.
55. G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296.
56. L. Leiserowitz, M. Tuval, Acta Crystallogr. Sect. B 1978, 34, 1230-1247.
57. J. C. Williams, A. E. McDermott, J. Phys. Chem. B 1998, 102, 6248-6259.
58. P. Lorente, I. G. Shenderovich, N. S. Golubev, G. S. Denisov, G. Buntkowsky, H.-H. Limbach, Magn. Reson. Chem. 2001, 39, S18-S29.
59. G. Buntkowsky, M. Taupitz, E. Roessler, H. M. Vieth, J. Phys. Chem. A 1997, 101, 67-75.
60. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
61. G. Bergerhoff, M. Berndt, K. Brandenburg, J. Res. Natl. Inst. Stand. Technol. 1996, 101, 221-225.
62. Diamond V3.1a, K. Brandenburg, Crystal Impact GbR, Bonn, 1997.
63. A. Pines, M. G. Gibby, J. S. Waugh, Chem. Phys. Lett. 1972, 15, 373-376.
64. J. S. Waugh, M. G. Gibby, A. Pines, S. Kaplan, Proceedings of the 17th Colloque Ampere, North-Holland Publishing Company, Amsterdam, 1972, p. 13.