Four different types of hydrogen bonds observed in 1,2-bis(N-benzenesulfonylamino)benzenes due to conformational properties of the sulfonamide moiety

Tetrahedron

Volumn 62, Issue 36, 2006, Pages 8458-8462

  Kato, Takako ^a   Masu, Hyuma ^a   Takayanagi, Hiroaki ^b   Kaji, Eisuke ^b   Katagiri, Kosuke ^a   Tominaga, Masahide ^a   Azumaya, Isao ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

Aromatic sulfonamide; Hydrogen bond; Synclinal conformation; X ray structure

Indexed keywords

1 (N BENZENESULFONYLAMINO) 2 (BENZENESULFONYL N METHYLAMINO)BENZENE; 1 (N METHYL N 4 TOLUENESULFONYLAMINO) 2 (N 4 TOLUENESULFONOYLAMINO)BENZENE; 1,2 BIS(N 4 TOLUENESULFONYLAMINO)BENZENE; 1,2 BIS(N BENZENESULFONYLAMINO)BENZENE; BENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR DYNAMICS; PRIORITY JOURNAL; RACEMIZATION; X RAY CRYSTALLOGRAPHY;

EID: 33746476298     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.087     Document Type: Article

References (27)

1. Maren T.H. Annu. Rev. Pharmacol. Toxicol. 16 (1976) 309-327
2. Scozzafava A., Owa T., Mastrolorenzo A., and Supuran C.T. Curr. Med. Chem. 10 (2003) 925-953
3. Supuran C.T., Scozzafava A., and Casini A. In: Supuran C.T., Scozzafava A., and Conway J. (Eds). Carbonic Anhydrase-Its Inhibitors and Activators (2004), CRC, Boca Raton, FL 67-147
4. Morzherin Y., Rudkevich D.M., Verboom W., and Reinhoudt D.N. J. Org. Chem. 58 (1993) 7602-7605
5. Kondo S., Suzuki T., and Yano Y. Tetrahedron Lett. 43 (2002) 7059-7061
6. Kavallieratos K., Rosenberg J.M., Chen W.-Z., and Ren T. J. Am. Chem. Soc. 127 (2005) 6514-6515
7. He L., An Y., Yuan L., Yamato K., Feng W., Gerlitz O., Zheng C., and Gong B. Chem. Commun. (2005) 3788-3790
8. Hu Z.-Q., and Chen C.-F. Chem. Commun. (2005) 2445-2447
9. Hu Z.-Q., and Chen C.-F. Tetrahedron 62 (2006) 3446-3454
10. Adsmond D.A., and Grant D.J.W. J. Pharm. Sci. 90 (2001) 2058-2077
11. Bock H., Nagel N., and Näther C. Chem.-Eur. J. 5 (1999) 2233-2236
12. Pedersen B.F., and Pedersen B. Tetrahedron Lett. (1965) 2995-3001
13. Bourn A.J.R., Gillies D.G., and Randall E.W. Tetrahedron 22 (1966) 1825-1829
14. Stewart W.E., and Siddall III T.H. Chem. Rev. 70 (1970) 517-551
15. Nanjan M.J., Kannappan V., and Genesan R. Indian J. Chem. 18B (1979) 461-463
16. Itai A., Toriumi Y., Tomioka N., Kagechika H., Azumaya I., and Shudo K. Tetrahedron Lett. 30 (1989) 6177-6180
17. Azumaya I., Kagechika H., Fujiwara Y., Itoh M., Yamaguchi K., and Shudo K. J. Am. Chem. Soc. 113 (1991) 2833-2838
18. Yamaguchi K., Matsumura G., Kagechika H., Azumaya I., Ito Y., Itai A., and Shudo K. J. Am. Chem. Soc. 113 (1991) 5474-5475
19. Itai A., Toriumi Y., Saito S., Kagechika H., and Shudo K. J. Am. Chem. Soc. 114 (1992) 10649-10650
20. Azumaya I., Kagechika H., Yamaguchi K., and Shudo K. Tetrahedron 51 (1995) 5277-5290
21. Tanatani A., Yamaguchi K., Azumaya I., Fukutomi R., Shudo K., and Kagechika H. J. Am. Chem. Soc. 120 (1998) 6433-6442
22. Azumaya I., Yamaguchi K., Okamoto I., Kagechika H., and Shudo K. J. Am. Chem. Soc. 117 (1995) 9083-9084
23. Azumaya I., Okamoto I., Nakayama S., Tanatani A., Yamaguchi K., Shudo K., and Kagechika H. Tetrahedron 55 (1999) 11237-11246
24. Azumaya I., Okamoto I., and Takayanagi H. Anal. Sci. 19 (2003) x3-x4 X-page
25. Azumaya I., Kato T., Okamoto I., Yamasaki R., Tanatani A., Yamaguchi K., Kagechika H., and Takayanagi H. Org. Lett. 5 (2003) 3939-3942
26. Bryan J.C., Rosenberg J.M., and Kavallieratos K. Acta Crystallogr. E61 (2005) o396-o397
27. Cheeseman G.W.H. J. Chem. Soc. (1955) 3308-3310