Cobaloximes with bis(thiophenyl)glyoxime: Synthesis and structure - Property relationship study

Organometallics

Volumn 28, Issue 12, 2009, Pages 3485-3491

  Dutta, Gargi ^a   Kumar, Kamlesh ^a   Gupta, B D ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AXIAL LIGAND; CO-C BOND; COBALOXIME; COBALOXIMES; DIOXIME; GLYOXIME; NMR CHEMICAL SHIFTS; STERIC BULK; STRUCTURE PROPERTY RELATIONSHIPS; THIOPHENYL; TRANS INFLUENCE; X-RAY STRUCTURE;

ALKYLATION; CHEMICAL BONDS; CYCLIC VOLTAMMETRY; MOLECULAR OXYGEN; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

COBALT COMPOUNDS;

EID: 67449168418     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900065k     Document Type: Article

References (64)

1. (a) Bresciani-Pahor, N.; Forcolin, M.; Marzilli, L. G.; Randaccio, L.; Summers, M. F.; Toscano, P. J. Coord. Chem. Rev. 1985, 63, 1, and references therein.
2. (b) Randaccio, L.; Bresciani-Pahor, N.; Zangrando, E.; Marzilli, L. G. Chem. Soc. Rev. 1989, 18, 225.
3. (c) Randaccio, L. Comments Inorg. Chem. 1999, 21, 327.
4. (d) Gupta, B. D.; Yamuna, R.; Singh, V.; Tiwari, U. Organometallics 2003, 22, 226.
5. (e) Gupta, B. D.; Qanungo, K.; Barcley, T.; Cordes, W. J. Organomet. Chem. 1998, 560, 155.
6. (f) Gupta, B. D.; Qanungo, K.; Yamuna, R.; Pandey, A.; Tiwari, U.; Vijaikanth, V.; Singh, V.; Barcley, T.; Cordes, W. J. Organomet. Chem. 2000, 608, 106.
7. (g) Gupta, B. D.; Roy, S. Inorg. Chim. Acta 1988, 146, 209.
8. (h) Gupta, B. D.; Mandal, D. Organometallics 2006, 25, 3305.
9. (i) Gupta, B. D.; Roy, S. Tetrahedron Lett. 1985, 26, 3609.
10. Golding, B. T.; Kemp, T. J.; Sell, C. S.; Sellars, P. J.; Watson, W. P. J. Chem. Soc., Perkin Trans. 2 1978, 839.
11. (a) Samsel, E. G.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 4790.
12. (b) Atkins, M. P.; Golding, B. T.; Sellers, P. J. J. Chem. Soc., Chem. Commun. 1978, 108, 954.
13. (a) Dodd, D.; Johnson, M. D.; Steeples, I. P.; McKenzie, E. D. J. Am. Chem. Soc. 1976, 98, 6399.
14. (b) Cooksey, C. J.; Dodd, D.; Johnson, M. D.; Lockman, B. L. J. Chem. Soc., Dalton Trans. 1978, 1814.
15. (c) McKenzie, E. D. Inorg. Chim. Acta 1978, 29, 107.
16. (a) Gupta, B. D.; Dixit, V.; Das, I. J. Organomet. Chem. 1999, 572, 49.
17. (b) Gupta, B. D.; Kumar, M.; Roy, S. Inorg. Chem. 1989, 28, 11.
18. (c) Gupta, B. D.; Roy, S. Tetrahedron Lett. 1984, 3255.
19. (d) Roy, S.; Das, I.; Bhanuprakash, K.; Gupta, B. D. Tetrahedron 1994, 50, 1847.
20. (e) Gupta, B. D.; Kumar, M. Inorg. Chim. Acta 1988, 149, 223.
21. (f) Gupta, B. D.; Das, I.; Dixit, V. J. Chem. Res. 1992, 306.
22. (g) Roy, M.; Kumar, M.; Gupta, B. D. Inorg. Chim. Acta 1986, 114, 87.
23. (h) Gupta, B. D.; Vijaikanth, V. J. Organomet. Chem. 2004, 689, 1102.
24. (a) Yohannes, P. G.; Bresciani-Pahor, N.; Randaccio, L.; Zangrando, E.; Marzilli, L. G. Inorg. Chem. 1988, 27, 4738.
25. (b) Summers, M. F.; Marzilli, L. G.; Bresciani-Pahor, N.; Randaccio, L. J. Am. Chem. Soc. 1984, 106, 4478.
26. (a) Marzilli, L. G.; Gerli, A.; Calafat, A. M. Inorg. Chem. 1992, 31, 4617.
27. (b) Hirota, S.; Polson, S. M.; Puckett, J. M., Jr.; Moore, S. J.; Mitchell, M. B.; Marzilli, L. G. Inorg. Chem. 1996, 35, 5646.
28. (c) Polson, S. M.; Cini, R.; Pifferi, C.; Marzilli, L. G. Inorg. Chem. 1997, 36, 314.
29. (a) Randaccio, L.; Furlan, M.; Geremia, S.; Slouf, M.; Srnova, I.; Toffoli, D. Inorg. Chem. 2000, 39, 3403.
30. (b) Randaccio, L.; Geremia, S.; Nardin, G.; Slouf, M.; Srnova, I. Inorg. Chem. 1999, 38, 4087.
31. (a) Mandal, D.; Gupta, B. D. Organometallics 2005, 24, 1501, and references therein.
32. (b) Gupta, B. D.; Qanungo, K. J. Organomet. Chem. 1997, 543, 125.
33. (c) Gupta, B. D.; Vijaikanth, V.; Singh, V. J. Organomet. Chem. 1998, 570, 1.
34. (d) Gupta, B. D.; Roy, M.; Das, I. J. Organomet. Chem. 1990, 397, 219.
35. (e) Gupta, B. D.; Tiwari, U.; Barcley, T.; Cordes, W. J. Organomet. Chem. 2001, 629, 83.
36. (f) Gupta, B. D.; Singh, V.; Yamuna, R. Organometallics 2003, 22, 2670.
37. (a) Mandal, D.; Gupta, B. D. Organometallics 2007, 26, 658.
38. (b) Xin, Z.; Han, D.; Li, Y.; Chen, H. Inorg. Chim. Acta 2006, 359, 1121.
39. (c) Drago, R. S. J. Organomet. Chem. 1996, 512, 61.
40. Gilaberte, J. M.; Lopez, C.; Alvarez, S.; Font-Bardia, M.; Solans, X. New J. Chem. 1993, 17, 193.
41. (a) Bhuyan, M.; Laskar, M.; Mandal, D.; Gupta, B. D. Organometallics 2007, 26, 3559.
42. (b) Dutta, G.; Laskar, M.; Gupta, B. D. Organometallics 2008, 27, 3338.
43. (a) International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV.
44. (b) Sheldrick, G. M. SHELXL-97: Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
45. SAINT +, 6.02 ed.; Bruker AXS: Madison, WI, 1999.
46. Sheldrick, G. M. SADABS, Empirical Absorption Correction Program; University of Göttingen: Göttingen, Germany, 1997.
47. XPREP, 5.1 ed.; Siemens Industrial Automation Inc.: Madison, WI, 1995.
48. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
49. (a) Ungnade, H. E.; Kissinger, L. W. Tetrahedron 1963, 19, 143.
50. (b) Ramprasad, D.; Busch, D. H. U.S. Patent 4,680,037, July 14, 1987.
51. Nicolaides, D. N.; Kouimtzis, A. Chim. Chronika 1974, 3, 63.
52. 13C NMR: C d N) 145.35, other carbons) 134.47, 128.51, 128.37, 128.10.
53. 2)) 3.26, 3.10 ppm, SEt group(Me)) 1.10 ppm, H-1) 1.25 ppm, O - H ··· O) 18.50 ppm.
54. 13C, C d N) represents the field effect.
55. (a) The dihedral angle (butterfly bending angle, R) is the angle between two dioxime planes of each cobaloxime unit.
56. (b) The positive sign of R and d indicates bending toward R and displacement toward the base and vice versa.
57. The torsion angle (τ) is the angle between two virtual planes that bisects the cobaloxime plane. Each plane is formed considering the middle point of the C - C bond of two oxime units that passes through cobalt and pyridine nitrogen.
58. Asaro, F.; Naradin, G.; Pellizer, G.; Perissini, S.; Randaccio, L.; Siega, P.; Tauzher, G.; Tavagnacco, C. J. Organomet. Chem. 2000, 601, 114.
59. (a) Dreos, R.; Geremia, S.; Nardin, G.; Randaccio, L.; Tauzher, G.; Vuano, S. Inorg. Chim. Acta 1998, 272, 74.
60. (b) Dreos, R.; Tauzher, G.; Vuano, S.; Asaro, F.; Pellizer, G.; Nardin, G.; Randaccio, L.; Geremia, S. J. Organomet. Chem. 1995, 505, 135.
61. Asaro, F.; Dreos, R.; Geremia, S.; Nardin, G.; Pellizer, G.; Randaccio, L.; Tauzher, G.; Vuano, S. J. Organomet. Chem. 1997, 548, 211.
62. (a) Elliott, C. M.; Hershenhart, E.; Finke, R. G.; Smith, B. L. J. Am. Chem. Soc. 1981, 103, 5558.
63. (b) Alexander, V.; Ramanujum, V. V. Inorg. Chim. Acta 1989, 156, 125.
64. Yamuna, R.; Gupta, B. D.; Mandal, D. Organometallics 2006, 25, 706.