Revealing the configuration and crystal packing of organic compounds by solid-state NMR spectroscopy: Methoxycarbonylurea, a case study

Chemistry - A European Journal

Volumn 10, Issue 19, 2004, Pages 4808-4816

  Macholl, Sven ^a,b   Börner, Frank ^c   Buntkowsky, Gerd ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b OTTO VON GUERICKE UNIVERSITY   (Germany)

^c FRAUNHOFER INSTITUTE FOR APPLIED POLYMER RESEARCH   (Germany)

Author keywords

Configuration determination; Hydrogen bonds; Molecular packing; NMR crystallography; REDOR

Indexed keywords

CRYSTALLIZATION; HYDROGEN BONDS; ISOTOPES; METHANE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYCRYSTALLINE MATERIALS;

CRYSTAL PACKING; INTERMOLECULAR ARRANGEMENT; POLYCRYSTALLINE METHOXYCARBONYLUREA; ROTATIONAL ECHO DOUBLE RESONANCE (REDOR);

ORGANIC COMPOUNDS;

METHOXYCARBONYLUREA; ORGANIC COMPOUND; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CHEMICAL COMPOSITION; CRYSTAL STRUCTURE; CRYSTALLIZATION; DERIVATIZATION; HYDROGEN BOND; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROTATIONAL ECHO DOUBLE RESONANCE SPECTROSCOPY; SIGNAL NOISE RATIO; SOLID STATE; SOLUBILITY; SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 5444243124     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400191     Document Type: Article

References (49)

1. F Borner, Synthese, Charakterisierung und Untersuchung von schwerloslichen Harnstoffderivaten als Grundlage fur Dungemittel, PhD Thesis, FU Berlin, 2000
2. S. Macholl, F Borner, G Buntkowsky, Z Phys Chem (Muenchen Ger.) 2003, 217, 1473-1505
3. G. Buntkowsky, I. Sack, H -H Limbach, B Kling, J. Fuhrhop, J. Phys Chem B 1997, 101, 11265-11272.
4. F Taulelle, C. Gérardin, M Haouas, C. Huguenard, V Munch, T. Loiseau, G. Férey, J Fluorine Chem 2000, 101, 269-272.
5. S M Reutzel-Edens, V A. Russell, L Yu, J Chem Soc, Perkin Trans 2 2000, 913-924
6. F Taulelle, C Huguenard, Stud Surf Sci Catal 2001, 135.
7. S M Reutzel-Edens, J. K. Bush, Am Pharm Rev. 2002, 5, 112-115
8. K Schmidt-Rohr, J Am Chem Soc 1996, 118, 7601.
9. S Macholl, I Sack, H -H Limbach, J Pauli, M Kelly, G Buntkowsky, Magn Reson. Chem 2000, 38, 596
10. I. Sack, Y. S. Balazs, S Rahimipour, S Vega, J. Magn Reson 2001, 148, 104-114
11. E Hughes, J. Jordan, T Gullion, J Phys Chem B 2001, 105, 5887-5891.
12. E Hughes, T Gullion, A. Goldbourt, S. Vega, A J Vega, J Magn Reson 2002, 156, 230-241
13. G. Goobes, S. Vega, J Magn. Reson 2002, 154, 236-251
14. A Goldbourt, S Vega, T Gullion, A. J Vega, J Am Chem Soc 2003, 125, 11194-11195
15. T. Gullion, R Kishore, T. Asakura, J Am Chem Soc 2003, 125, 7510-7511
16. T. Gullion, J Schaefer, Adv Magn Opt Reson 1989, 13, 57
17. SPARTAN, Wavefunction, Inc , 18401 Karman Avenue, Suite 370, Irvine, CA 92612 (USA), 1995
18. K T. Mueller, T P Jarvie, D J Aurentz, B W Roberts, Chem Phys Lett. 1995, 242, 535
19. J. D'espinose De La Caillerie, C. Fretigny, J Magn Reson. 1998, 133, 273
20. J. M Goetz, J Schaefer, J Magn Reson 1997, 127, 147
21. C. A. Fyfe, A R Lewis, J. M Chezeau, H. Grondey, J Am Chem. Soc 1997, 119, 12210-12222.
22. M Bertmer, H. Eckert, Solid State Nucl Magn Reson 1999, 15, 139-152
23. C A. Michal, L W Jehnski, J Am Chem Soc 1997, 119, 9059-9060
24. A E Bennett, L R Becerra, R G Griffin, J Chem Phys 1994, 100, 812
25. A E. Bennett, C. M. Rienstra, P T Lansbury, R G Griffin, J Chem Phys 1996, 105, 10289
26. T Gullion, C Pennington, Chem Phys Lett 1998, 290, 88-93
27. O Liivak, D B Zax, J Chem Phys 2000, 113, 1088-1096.
28. Gaussian 98, Rev B 2, M J Frisch, G. W. Trucks, H. B. Schlegel, G E Scuseria, M A Robb, J R. Cheeseman, V. G. Zakrzewski, J Montgomery, Jr., 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. Raghavachan, 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., Pittsburgh, PA, 1998.
29. A D Becke, J Chem Phys 1993, 98, 5648.
30. C Lee, W. Yang, R G. Parr, Phys Rev. B 1988, 37, 785
31. A E Bennett, C M Rienstra, M Auger, K V Lakshmi, R G. Griffin, J Chem Phys 1995, 103, 6951.
32. G Metz, X Wu, S. O. Smith, J Magn Reson , Ser A 1994, 110, 219-227.
33. T. Gullion, D B Baker, M S. Conradi, J Magn Reson 1990, 89, 479
34. T Gullion, J Schaefer, J Magn Reson 1991, 92, 439
35. Y Li, J. N S Evans, J Magn Reson , Ser A 1995, 116, 150
36. T Gullion, J Schaefer, J Magn Reson 1989, 81, 196
37. A. E. Bennett, R. G. Griffin S Vega, Springer Series in NMR 1994, 33
38. J Garbow, T. Gullion in Carbon-13 NMR Spectroscopy of Biological Systems (Ed N. Beckmann), Academic Press Inc , New York, 1995, pp 65-115
39. I Sack, S. Macholl, J H Fuhrhop, G. Buntkowsky, Phys Chem Chem Phys 2000, 2, 1781
40. A. Naito, K Nishimura, S Tuzi, H. Saito, Chem Phys Lett 1994, 229, 506-511
41. K Nishimura, A. Naito, S Tuzi, H Saito, J Phys Chem B 1999, 103, 8398-8404.
42. M Bak, J. T Rasmussen, N C Nielsen, J Magn Reson 2000, 147, 296-330.
43. M. Bak, N. C Nielsen, J Magn Reson 1997, 125, 132-139.
44. L Leiserowitz, M Tuval, Acta Crystallogr Sect B 1978, 34, 1230-1247
45. J C Williams, A. E. McDermott, J Phys Chem B 1998, 102, 6248-6259.
46. B Sepehrnia, J R Ruble, G A. Jeffrey, Acta Crystallogr Sect C 1987, 43, 249-251
47. S Macholl, Determination of Molecular Structures by Dipolar Solid State NMR Spectroscopy, PhD Thesis, FU Berlin, 2002
48. A I Kitaigorodski, Molekulkristalle, 1st ed , Akademie-Verlag, Berlin, 1979
49. Y Wang, B Wei, Q. Wang, J Crystallogr Spectrosc Res 1990, 20, 1990