Structural Implications of C-H⋯S Contacts in Organophosphorus Compounds. Studies of 1,6-Anhydro-2-O-tosyl-4-S- (5,5-dimethyl-2-thioxa-1,3,2-dioxaphosphorinan-2-yl)-β-D-glucopyranose by X-ray and Solid-State NMR Methods

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4209-4217

  Potrzebowski, Marek J ^a   Michalska, Maria ^b   Koziol, Anna E ^c   Kazmierski, Sławomir ^a   Lis, Tadeusz ^d   Pluskowski, January ^b   Ciesielski, Włodzimierz ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b MEDICAL UNIVERSITY OF LODZ   (Poland)

^c MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

^d UNIVERSITY OF WROC AW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000219674     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971294i     Document Type: Article

References (45)

1. Jeffrey, G. A.; Saenger, W. In Hydrogen Bonding in Biological Structures, Springer-Verlag: Berlin, Heidelberg, New York, 1991.
2. Lehn, J.-M. In Supramolecular Chemistry, Concepts and Perspectives, VCH: Weinheim, New York, Basel, Cambridge, Tokyo, 1995.
3. Sarma, J. A. R. P.; Desiraju, G. R. Acc. Chem. Res. 1986, 19, 222.
4. Steiner, T. J. Chem. Soc., Perkin Trans. 2 1995, 1315.
5. Allen, F. H.; Howard, J. A. K.; Hoy, V. J.; Desiraju, G. R.; Reddy, D. S.; Wilson, C. C. J. Am. Chem. Soc. 1996, 118, 4081.
6. Steiner, T.; Tamm, M.; Lutz, B.; van der Maas, J. J. Chem. Soc. Chem. Commun. 1996, 1127.
7. Steiner, T.; Saenger, W. J. Am. Chem. Soc. 1993, 115, 4540.
8. Viswamitra, M. A.; Radhakrishnan, R.; Bandekar, J.; Desiraju, G. R. J. Am. Chem. Soc. 1993, 115, 4868.
9. Zaworotko, M. Chem. Soc. Rev. 1994, 23, 283.
10. Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665.
11. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
12. Sutor, D. J. Nature 1962, 68, 195.
13. Sutor, D. J.J. Chem. Soc. 1963, 1105.
14. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063.
15. Steiner, T.; Saenger, W. J. Am. Chem. Soc. 1992, 114, 10146.
16. Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290.
17. Desiraju, G. R. Ace. Chem. Res. 1996, 29, 441.
18. Auffinger, P.; Louise-May, S.; Westhof, E. J. Am. Chem. Soc. 1996, 118, 1181.
19. Novoa, J. J.; Carme Rovira, M.; Rovira, C.; Veciane, J.; Tarres, J. Adv. Mater. 1995, 7, 233.
20. Steiner, T. J. Chem. Soc. Chem. Commun. 1994, 101.
21. Steiner, T.; Kanters, J. M.; Kroon, J. J. Chem. Soc. Chem. Commun. 1996, 1277.
22. CSD REFCODEs are deposited as Supporting Information.
23. Bondi, A. J. Phys. Chem. 1964, 68 441.
24. Kroon, J.; Kanters, J. A.; van Duijeveldt de Rijdt, J. G. C. M.; Vliegenhardt, J. J. Mol. Str. 1975, 24, 109.
25. Desiraju, G. R.; Sharma, C., V., K. J. Chem. Soc. Chem. Commun. 1991, 1239.
26. Braga, D.; Grepioni, F.; Biradha, K.; Pedireddi, V. R.; Desiraju, G. R. J. Am. Chem. Soc. 1995, 117, 3156.
27. WINMAS program, version 940108, Bruker-Franzen Analytik GMBH, Bremen 1994.
28. Herzfeld, J.; Berger, A. J. Chem. Phys. 1980, 73, 6021.
29. (b) Jeschke, G.; Grossmann, G. J. Magn. Reson. 1993, A103, 323.
30. Potrzebowski, M. J.; Michalski, J. In Phosphorus-31 NMR Spectral Properties in Compound Characterization and Structural Analysis; Quin, L. D., Verkade, J. G., Eds.; VCH: 1994; pp 413-426.
31. Grossmann, G.; Beckmann, H.; Rademacher, O.; Krueger, K.; Ohms, G.; J. Chem. Soc., Dalton Trans. 1995, 2797.
32. Potrzebowski, M. J. J. Chem. Soc., Perkin Trans. 2, 1993, 63.
33. Krüger, K.; Grossmann, G.; Fleischer U.; Franke, R.; Kutzelnigg, W. Magn. Reson. Chem. 1995, 33.
34. Jelinski, L. W. In High Resolution NMR Spectroscopy of Synthetic Polymers in Bulk; Komoroski, R. A., Ed.; VCH Publishers: 1986; Chapter 10, pp 335-364.
35. Kristensen, J. H.; Bildsoe, H.; Jakobsen H. J.; Nielsen N. Ch. J. Magn. Reson. 1992, 92, 443.
36. Poupko, R.; Olender, Z.; Reichert, D.; Luz, Z. J. Magn. Reson. 1994, 106, 113.
37. Potrzebowski, M. J.; Wasiak J.; Ciesielski, W.; Klinowski, J. J. Magn. Reson. 1995, A114, 70.
38. Marks, D.; Zumbulyadis, N.; Vega, S. J. Magn. Reson. 1996, A122, 16.
39. Zumbulyadis, N.; O'Reily, J. M. J. Am. Chem. Soc. 1993, 115, 4407.
40. Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1994, 116, 4463.
41. Carroll, M. T.; Bader, R. F. W. Mol. Phys. 1988, 65, 695.
42. Sheldrick, G. M. SHELXS. Program for structure solution; University of Göttingen: Göttingen, Germany, 1986.
43. Sheldrick, G. M. SHELXL-93. Program for crystal structure refinement; University of Göttingen: Göttingen, Germany, 1993.
44. Mason, J. Solid State Nucl. Magn. Reson. 1993, 2, 285.
45. Michalska, M.; Kudelska, W.; Pluskowski, J.; Kozioł, A. E.; Lis, T. J. Chem. Soc. Perkin Trans 1 1994, 979.