Oxazoline chemistry - Part IV: Synthesis and characterization of oxazoline complexes of the zinc halides

Canadian Journal of Chemistry

Volumn 81, Issue 12, 2003, Pages 1482-1491

  Barclay, Tosha M ^a   Del Río, Ignacio ^b   Gossage, Robert A ^c   Jackson, Sarah M ^c  

^a North Harris College   (United States)

^b UNIVERSITY OF OVIEDO   (Spain)

^c ACADIA UNIVERSITY   (Canada)

Author keywords

Coordination complex; NMR spectroscopy; Oxazoline; X ray crystal structure; Zinc; Zn(II)

Indexed keywords

COMPLEXATION; DERIVATIVES; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION; ZINC COMPOUNDS;

HYGROSCOPIC COMPLEXES; LIGANDS; STRUCTURAL DIVERSITY;

ORGANIC COMPOUNDS;

HALIDE; OXAZOLINE DERIVATIVE; ZINC COMPLEX;

ARTICLE; CRYSTAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION;

EID: 1042286462     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v03-166     Document Type: Article

References (67)

1. (a) S. Rahuel-Clermont and M.F. Dunn. The biological chemistry of zinc. In Copper and zinc in inflammatory and degenerative diseases. Edited by K.D. Rainsford, R. Milanino, J.R.J. Sorenson, and G.P. Velo. Kluwer Academic Publications, Boston. 1998. Chap 4, pp. 47-59;
2. (b) J.F. Riordan. Med. Clin. N. Am. 60, 661 (1976);
3. (c) B.L. Vallee and D.S. Auld. Biochemistry, 29, 5647 (1990);
4. (d) C.L. Keen and M.E. Gershwin. Ann. Rev. Nutr. 10, 415 (1990);
5. (e) B.L. Vallee and D.S. Auld. Acc. Chem. Res. 26, 543 (1993).
6. F.A. Cotton and G. Wilkinson. Advanced inorganic chemistry. 4th ed. John Wiley & Sons, Toronto. 1980. Chap 19, pp. 589-616.
7. C. Hu and U. Englert. CrystEngComm. 23, 1 (2001).
8. (a) W.L. Steffen and G.J. Palenik. Inorg. Chem. 16, 1119 (1977);
9. (b) W.L. Steffen and G.J. Palenik. Acta Cryst. B32, 298 (1976);
10. (c) H. Lynton and M.C. Sears. Can. J. Chem. 49, 3418 (1971);
11. (d) S. İde, A. Ataç, and Ş. Yurdakul. J. Molecular Struct. 605, 103 (2002).
12. (a) B.K.S. Lundberg. Acta Cryst. 21, 901 (1966);
13. (b) N. Galván-Tejada, S. Bernès, S.E. Castillo-Blum, H. Nöth, R. Vicente, and N. Barba-Behrens. J. Inorg. Biochem. 91, 339 (2002).
14. C. Hu and U. Englert. Acta Cryst. C57, 1251 (2001).
15. B. Hajjem, A. Kallel, I. Svoboda, and J. Sakurai. Acta Cryst. C48, 1002 (1992).
16. Purine: (a) H.L. Laity and M.R. Taylor. Acta Cryst. C51, 1791 (1995); Quinoline: (b) Y. Cui, D. Long, W. Chen, and J. Huang. Acta Cryst. C54, 1605 (1998); Thiadiazole: (c) K.Sh. Khusenov, B.B. Umarov, M.M. Ishankhodzhaeva, N.A. Parpiev, S.A. Talipov, and B.T. Ibragimov. Koord. Khim. 23, 596 (1997); Russ. J. Coord. Chem. 23, 555 (1997); Antazoline: (d) M. Parvez and M. Rusiewicz. Acta Cryst. C51, 2277 (1995); Guanine: (e) F. Zamora and M. Sabat. Inorg. Chem. 41, 4976 (2002).
17. Purine: (a) H.L. Laity and M.R. Taylor. Acta Cryst. C51, 1791 (1995); Quinoline: (b) Y. Cui, D. Long, W. Chen, and J. Huang. Acta Cryst. C54, 1605 (1998); Thiadiazole: (c) K.Sh. Khusenov, B.B. Umarov, M.M. Ishankhodzhaeva, N.A. Parpiev, S.A. Talipov, and B.T. Ibragimov. Koord. Khim. 23, 596 (1997); Russ. J. Coord. Chem. 23, 555 (1997); Antazoline: (d) M. Parvez and M. Rusiewicz. Acta Cryst. C51, 2277 (1995); Guanine: (e) F. Zamora and M. Sabat. Inorg. Chem. 41, 4976 (2002).
18. Purine: (a) H.L. Laity and M.R. Taylor. Acta Cryst. C51, 1791 (1995); Quinoline: (b) Y. Cui, D. Long, W. Chen, and J. Huang. Acta Cryst. C54, 1605 (1998); Thiadiazole: (c) K.Sh. Khusenov, B.B. Umarov, M.M. Ishankhodzhaeva, N.A. Parpiev, S.A. Talipov, and B.T. Ibragimov. Koord. Khim. 23, 596 (1997); Russ. J. Coord. Chem. 23, 555 (1997); Antazoline: (d) M. Parvez and M. Rusiewicz. Acta Cryst. C51, 2277 (1995); Guanine: (e) F. Zamora and M. Sabat. Inorg. Chem. 41, 4976 (2002).
19. Purine: (a) H.L. Laity and M.R. Taylor. Acta Cryst. C51, 1791 (1995); Quinoline: (b) Y. Cui, D. Long, W. Chen, and J. Huang. Acta Cryst. C54, 1605 (1998); Thiadiazole: (c) K.Sh. Khusenov, B.B. Umarov, M.M. Ishankhodzhaeva, N.A. Parpiev, S.A. Talipov, and B.T. Ibragimov. Koord. Khim. 23, 596 (1997); Russ. J. Coord. Chem. 23, 555 (1997); Antazoline: (d) M. Parvez and M. Rusiewicz. Acta Cryst. C51, 2277 (1995); Guanine: (e) F. Zamora and M. Sabat. Inorg. Chem. 41, 4976 (2002).
20. Purine: (a) H.L. Laity and M.R. Taylor. Acta Cryst. C51, 1791 (1995); Quinoline: (b) Y. Cui, D. Long, W. Chen, and J. Huang. Acta Cryst. C54, 1605 (1998); Thiadiazole: (c) K.Sh. Khusenov, B.B. Umarov, M.M. Ishankhodzhaeva, N.A. Parpiev, S.A. Talipov, and B.T. Ibragimov. Koord. Khim. 23, 596 (1997); Russ. J. Coord. Chem. 23, 555 (1997); Antazoline: (d) M. Parvez and M. Rusiewicz. Acta Cryst. C51, 2277 (1995); Guanine: (e) F. Zamora and M. Sabat. Inorg. Chem. 41, 4976 (2002).
21. Purine: (a) H.L. Laity and M.R. Taylor. Acta Cryst. C51, 1791 (1995); Quinoline: (b) Y. Cui, D. Long, W. Chen, and J. Huang. Acta Cryst. C54, 1605 (1998); Thiadiazole: (c) K.Sh. Khusenov, B.B. Umarov, M.M. Ishankhodzhaeva, N.A. Parpiev, S.A. Talipov, and B.T. Ibragimov. Koord. Khim. 23, 596 (1997); Russ. J. Coord. Chem. 23, 555 (1997); Antazoline: (d) M. Parvez and M. Rusiewicz. Acta Cryst. C51, 2277 (1995); Guanine: (e) F. Zamora and M. Sabat. Inorg. Chem. 41, 4976 (2002).
22. See, for example: P.J. Blower. Ann. Rep. Prog. Chem. Sect. A. 95, 631 (1999); 96, 645 (2000); 97, 587 (2001); 98, 615 (2002).
23. See, for example: P.J. Blower. Ann. Rep. Prog. Chem. Sect. A. 95, 631 (1999); 96, 645 (2000); 97, 587 (2001); 98, 615 (2002).
24. See, for example: P.J. Blower. Ann. Rep. Prog. Chem. Sect. A. 95, 631 (1999); 96, 645 (2000); 97, 587 (2001); 98, 615 (2002).
25. See, for example: P.J. Blower. Ann. Rep. Prog. Chem. Sect. A. 95, 631 (1999); 96, 645 (2000); 97, 587 (2001); 98, 615 (2002).
26. (a) A. Monstrolorenzo, A. Scozzafava, and C.T. Supuran. Eur. J. Pharm. Sci. 11, 99 (2000);
27. (b) K.D. Rainsford and M.W. Whitehouse. J. Pharm. Pharmacol. 44, 476 (1992);
28. (c) A. Scozzafava, L. Menabuoni, F. Minicione, G. Minicione, and C.T. Supuran. Bioorg. Med. Chem. Lett. 11, 575 (2001);
29. (d) Tz.B. Kovachev, P.N. Stamberov, D.S. Ivanov, M.K. Mitcheva, S.P. Marinova, H.A. Astroug, and J.N. Stoychkov. Pharmazie, 49, 25 (1994);
30. (e) G. Abou-Mohamed, A. Papapetropoulos, J.D. Catavas, and R.W. Caldwell. Eur. J. Pharmacol. 341, 265 (1998).
31. J. García-Cañadas, J.M. Pérez, A.G. Quiroga, M.A. Fuertas, C. Alonso, and C. Navarro-Ranninger. J. Chem. Soc. Dalton Trans. 2283 (2002).
32. (a) B.A. Katz, J.M. Clark, J.S. Finer-Moore, T.E. Jenkins, C.R. Johnson, M.J. Ross, C. Luong, W.R. Moore, and R.M. Stroud. Nature (London), 391, 608 (1998);
33. (b) A. Whitney, G. Gavory, and S. Balasubramanian. Chem. Commun. 36 (2003);
34. (c) Y. Yoshikawa, E. Ueda, H. Sakurai, and Y. Kojima. Chem. Pharm. Bull. 51, 230 (2003);
35. (d) H. Sakurai, Y. Kojima, Y. Yoshima, K. Kawabe, and H. Yasui. Coord. Chem. Rev. 226, 187 (2002);
36. (e) C.H. Stammer, A.N. Wilson, C.F. Spencer, F.W. Bachelor, F.W. Holly, and K. Folkers. J. Am. Chem. Soc. 79, 3236 (1957);
37. (f) H.R. Onishi, B.A. Pelak, L.S. Gerckens, L.L. Silver, F.W. Kahan, M.-H. Chen, A.A. Patchett, S.M. Galloway, S.A. Hyland, M.S. Anderson, and C.R.H. Raetz. Nature (London), 274, 980 (1996);
38. (g) M.-H. Chen, M.G. Steiner, S.E. de Laszlo, A.A. Patchett, M.S. Anderson, S.A. Hyland, H.R. Onishi, L.L. Silver, and C.R.H. Raetz. Bioorg. Med. Chem. Lett. 9, 313 (1999);
39. (h) T. Kline, N.H. Anderson, E.A. Harwood, J. Bowman, A. Malada, S. Endsley, A.L. Erwin, M. Doyle, S. Fong, A.L. Harris, B. Mendelsohn, K. Mdluli, C.R.H. Raetz, C.K. Stover, P.R. White, A. Yabannavar, and S. Zhu. J. Med. Chem. 45, 3112 (2002);
40. (i) M.C. Rirrung, N. Tumey, A.L. McClerren, and C.R.H. Raetz. J. Am. Chem. Soc. 125, 1575 (2003).
41. I. del Río, R.A. Gossage, M.S. Hannu, M. Lutz, A.L. Spek, and G. van Koten. Can. J. Chem. 78, 1620 (2000).
42. (a) K.M. Button and R.A. Gossage. J. Heterocyclic Chem. 40, 513 (2003);
43. (b) J.T. Banks, K.M. Button, R.A. Gossage, T.D. Hamilton, and K.E. Kershaw. Heterocycles, 55, 2251 (2001);
44. (c) K.M. Button, R.A. Gossage, and R.K.R. Phillips. Synth. Commun. 32, 363 (2002);
45. (d) K.M. Button, R.A. Gossage, and H. Jenkins. Poster P-207. International Conference on Organometallic Chemistry. 20th. Corfu, Greece. 2002.
46. M. Gómez, G. Muller, and M. Rocamora. Coord. Chem. Rev. 193-195, 769 (1999), and refs. therein.
47. (a) H. Witte and W. Seeliger. Liebigs Ann. Chem. 999 (1974);
48. (b) A.I. Meyers. J. Heterocyclic Chem. 35, 991 (1998), and refs. therein.
49. (a) D.J. Darensbourg, S.J. Lewis, J.L. Rodgers, and J.C. Yarbrough. Inorg. Chem. 42, 581 (2003);
50. (b) E. Şahin, S. İde, A. Ataç, and Ş. Yurdakul. J. Molecular Struct. 616, 253 (2002);
51. (c) E. Şahin, S. İde, M. Kurt, and Ş. Yurdakul. J. Molecular Struct. 616, 259 (2002).
52. (a) J. Ni, Y. Xie, X. Liu, and Q. Liu. Appl. Organomet. Chem. 17, 315 (2003);
53. (b) K. Davarski, J. Macicek, and L. Konovalov. J. Coord. Chem. 38, 123 (1996).
54. L.M. Richberg, J.A. Farouq, C.D. Incarvito, A.L. Rheingold, and D. Rabinovich. Polyhedron, 19, 1815 (2000).
55. (a) E. Libertini, K. Yoon, and G. Parkin. Polyhedron, 12, 2539 (1993);
56. (b) J. Pickardt and P. Droas. Acta Cryst. C45, 360 (1989).
57. C. Bolm, K. Weickhardt, M. Zehnder, and T. Ranff. Chem. Ber. 124, 1173 (1991).
58. J. Castro, S. Cabeliero, P. Perez-Lourido, J. Romero, J.A. García-Vásquez, and A. Sousa. Z. Anorg. Allg. Chem. 628, 1210 (2002).
59. G.K. Patra, I. Goldberg, A. Sarkar, S. Chowdhury, and D. Datta. Inorg. Chim. Acta, 344, 7 (2003).
60. H. Kooijman, A.L. Spek, C. Zondervan, and B.L. Feringa. Acta Cryst. E58, m429 (2002).
61. C. Pettinari, A. Cingolani, and B. Bovio. Polyhedron, 15, 115 (1996).
62. M.A. Weinberger and R. Greenhalgh. Can. J. Chem. 41, 1038 (1963).
63. P. Coppens. In Crystallographic computing. Edited by F.R. Ahmed, S.R. Hall, and C.P. Huber. Munksgaard, Copenhagen. 1970. pp. 255-270.
64. P.T. Beurskens, G. Beurskens, W.P. Bosman, R. de Gelder, S. García-Granda, R.O. Gould, R. Israël, and J.M.M. Smits. The DIRDIF-96 program system [computer program]. Crystallography Laboratory, University of Nijmegen, The Netherlands. 1996.
65. G.M. Sheldrick. SHELXL97 [computer program]. Version 97-2. University of Göttingen, Germany. 1997.
66. A.L. Spek. The EUCLID package. In Computational crystallography. Edited by D. Sayre. Clarendon Press, Oxford, U.K. 1982. p. 528.
67. L.J. Farrugia. J. Appl. Crystallogr. 32, 837 (1999).