X-ray investigations of sulfur-containing fungicides. II. Intramolecular forces governing the conformation of four novel α-phenylazo- and α-phenylhydrazono-β-ketosulfones

Acta Crystallographica Section B: Structural Science

Volumn 57, Issue 1, 2001, Pages 54-62

  Wolf, W M ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

FUNGICIDE; SULFONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; FUNGICIDES, INDUSTRIAL; HYDROGEN BONDING; MOLECULAR STRUCTURE; SULFONES;

EID: 0035257140     PISSN: 01087681     EISSN: None     Source Type: Journal    
DOI: 10.1107/S0108768100013197     Document Type: Article

References (49)

1. Alder, R. W., Carniero, T. M. G., Mowlam, R. W., Orpen, G., Petillo, P. A., Vachon, D. J., Weisman, G. R. & White, J. M. (1999). J. Chem. Soc. Perkin Trans. 2. pp. 589-599.
2. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1992). International Tables for Crystallography, edited by A. J. C. Wilson, Vol. C. pp. 691-705. Dordrecht: Kluwer Academic Publishers.
3. Becke, A. D. (1993). J. Chem. Phys. 98, 5648-5652.
4. Bertolasi, V., Ferretti, V., Gilli, P., Gilli, G., Issa, Y. M. & Sherif, O. E. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 2223-2228.
5. Bertolasi, V., Gilli, P., Ferretti, V. & Gilli, G. (1991). J. Am. Chem. Soc. 113, 4917-4925.
6. Bertolasi, V. Gilli, P., Ferretti, V. & Gilli, G. (1994). Acta Cryst. B50, 617-625.
7. Bertolasi, V. Nanni, L., Gilli, P., Ferretti, V., Gilli, G., Issa, Y. M. & Sherif, O. E. (1994). New J. Chem. 18, 251-261.
8. Besler, B. H., Merz Jr, K. M. & Kollman, P. A. (1990). J. Comput. Chem. 11, 431-439.
9. Bondi, A. (1964). J. Phys. Chem. 68, 441-451.
10. Brockway, L. O. (1937). J. Phys. Chem. 41, 185-195.
11. Cramer, J. C. (1996). J. Mol. Struct. (Theochem.) 370, 135-146.
12. Dal Colle, M., Bertolasi, V., de Palo, M., Distefano, G., Jones, D., Modelli, A. & Olivato, P. R. (1995). J. Phys. Chem. 99, 15011-15017.
13. Distefano, G., Dal Colle, M., Bertolasi, V., Olivato, P. R., Bonfada, O. & Mondino, M. G. (1991). J. Chem. Soc. Perkin Trans. 2, pp. 1195-1199.
14. Distefano, G., Dal Colle, M., de Palo, M., Jones, D., Bombieri, G., Del Pra, A., Olivato, P. R. & Mondino, M. G. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 1661-1669.
15. Fleming, I. (1976). Frontier Orbitals and Organic Chemical Reactions, p. 209. Chichester: Wiley.
16. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman., J. R., Zakrzewski, V. G., Montgomery Jr. J. A., Stratmann, R. E., Burant, J. C., Dappich, S., Millam, J. M., Daniels, A. D., Kudin, K. N., Strain, M. C., Farkas, O., Tomasi, J., Barone, V. Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P. Y., Cui, Q, Morokuma, K., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ciosłowski, J., Ortiz, J. V., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, O. M. W., Johnson, B. G., Chen, W., Wong, J. L., Andres, J. L., Head-Gordon, M., Replogle, E. S. & Pople, J. A. (1998). GAUSSIAN98. Revision A.6. Gaussian Inc., Pittsburgh PA, USA.
17. Gałdecki, Z., Kowalski, A. & Uszyñski, L. (1995). DATAPROC, Version 9.0. Kuma Diffraction, Wroclaw, Poland.
18. Gilli, G., Bellucci, F., Ferretti, V. & Bertolasi, V. (1989). J. Am. Chem. Soc. 111, 1023-1028.
19. Gilli, P., Bertolasi, V., Ferretti, V. & Gilli, G. (1994). J. Am. Chem. Soc. 116, 909-915.
20. Gómez-Sánchez, A., García Martín, M. G., Borrachero, P. & Bellanoto, J. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 301-306.
21. Graczyk, P. R. & Mikołajczyk, M. (1994). Topics in Stereochemistry, edited by E. L. Eliel and S. H. Wilen, pp. 159-349. New York: Wiley.
22. Grossert, J. S., Ranjith, H., Dharmaratne, T., Cameron, T. S. & Vincent, B. R. (1987). Can. J. Chem. 66, 2860-2869.
23. Hansch, C. & Leo, A. (1979). Substituent Constants for Correlation Analysis in Chemistry and Biology. Weinheim: Verlag Chemie.
24. Hasall, K. A. (1982). The Chemstry of Pesticides. Their Metabolism, Mode of Action and Uses in Crop Protection, p. 179. Wienheim: Verlag Chemie.
25. Hoffmann, R. (1971). Acc. Chem. Res. 4, 1-9.
26. Hohenberg, P. & Kohn, W. (1964). Phys. Rev. B, 136, 864-871.
27. Juaristi, E. & Cuevas, G. (1995). The Anomeric Effect. Boca Raton: CRC Press.
28. Kucsman, A. & Kapovits, J. (1985). Organic Sulfur Chemistry. Theoretical and Experimental Advances, edited by F. Bernardi, I. G. Csizmadia and A. Mangini, pp. 226-245. Amsterdam: Elsevier.
29. Kuma Diffraction (1991). KM-4 User's Guide, Version 3.2. Kuma Diffraction, Wroclaw. Poland.
30. Lee, C. Yang, W. & Parr, R. G. (1988). Phys. Rev. B, 37, 785-789.
31. Levy, M. (1979). Proc. Natl. Acad. Sci. USA, 76, 6062-6065.
32. Mayer, I. (1986). Int. J. Quantum Chem. 29, 477-483.
33. Molecular Simulations Inc. (1996). DMOL User Guide. Version 96.0. Molecular Simulations Inc., San Diego, USA.
34. Olivato, P. R., Guerrero, S. A. & Zukerman-Schpector, J. (2000). Acta Cryst. B56, 112-117.
35. Olivato, P. R., Mondino, M. G., Yreijo, M. H., Blanka, W., Bjorklund, M. B., Marzorati, L., Distefano, G., Dal Colle, M., Bombieri, G. & Del Pra, A. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 109-114.
36. Roberts, J. D., Webb, R. L. & McElhill, A. (1950). J. Am. Chem. Soc. 72, 408-111.
37. Rüchardt, Ch. & Beckhaus, H.-D. (1985). Angew. Chem. Int. Ed. Engl. 24, 529-538.
38. Sheldrick, G. M. (1997a). SHELXL97. University of Göttingen, Germany.
39. Sheldrick, G. M. (1997b). SHELXS97. University of Göttingen, Germany.
40. Siemens (1989). P3, Version 2.0. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
41. Siemens (1990). XP, Version 4.1. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
42. Siemens (1991). XDISK, Version 4.20. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
43. Singh, U. C. & Kollman, P. A. (1984). J. Comput. Chem. 5, 129-145.
44. TRIPOS Associates Inc. (1996). SYBYL, Version 6.3. TRIPOS Associates Inc., St Louis, Missouri, USA.
45. Wolf, W. M. (1999a). Acta Cryst. C55, 469-472.
46. Wolf, W. M. (1999b). J. Mol. Struct. 474, 113-124.
47. Zakrzewski, A. (1996). Private communication.
48. Zakrzewski, A. (1999). Przemysł Chemiczny, 78, 17-19.
49. Zakrzewski, A. & Kacała, A. (1998). Pestycydy, 4, 21-30.