Desulfuration and cyclization of (Z)-2-[amino(pyridine-2-yl)methylene]- hydrazonecarbothioamide in the presence of manganese(II)

Zeitschrift fur Anorganische und Allgemeine Chemie

Volumn 634, Issue 15, 2008, Pages 2907-2916

  Castiñeiras, Alfonso ^a   Garcia Santos, Isabel ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Crystal structures; Manganese; Self assembly; Supramolecular chemistry; Thiosemicarbazones

Indexed keywords

EID: 57349086073     PISSN: 00442313     EISSN: 15213749     Source Type: Journal    
DOI: 10.1002/zaac.200800326     Document Type: Article

References (86)

1. (a) B. S. Garg, M. R. P. Kurup, Y. K. Bhon, Trans. Met. Chem. 1988, 13, 92;
2. (b) P. Bindu, M. R. P. Kurup, J. I. Baht, J. Electrochim. Soc. India 1999, 48, 154;
3. (c) S. Chandra, G. Singh, V. P. Tyagi, S. Raizada. Synth. React. Inorg. Met.-Org. Chem. 2001, 31, 1759;
4. (d) H. A. Tang, L. F. Wang, R. D. Yang, Trans. Met. Chem. 2003, 28, 395.
5. (a) M. B. Ferrari, G. Gasparri Fava, C. Pelizzi, P. Tarasconi, G. Tosi, J. Chem. Soc. Dalton Trans. 1987, 227;
6. (b) A. Usman, I. A. Razak, S. Chantraproma, H.-K. Fun, A. Sreekanth, S. Sivakumar, M. R. P. Kurup, Acta Crystallogr. 2002, C58, m461;
7. (c) D. Kovala-Demertzi, U. Gangadhatmath, M. A. Demertzis, Y. Sanakis, Inorg. Chem. Commun. 2005, 8, 619;
8. (d) A. Sreekanth, M. Joseph, H.-K. Fun, M. R. P. Kurup, Polyhedron 2006, 25, 1408;
9. (e) V. Philip, V. Suni, M. R. P. Kurup, M. Nathaji, Spectrochim. Acta 2006, 64A, 171.
10. (a) B. Kok, B. Forbush, M. McGloim, Photochem Photobiol. 1970, 11, 457;
11. (b) G. M. Cheniae, M. Martin, Biochim. Biophys. Acta 1970, 197, 219.
12. (a) I. Fridovich, Adv. Inorg. Biochem. 1979, 1, 67;
13. (b) J. Limburg, J. S. Vrettos, M. L. Liable-Sands, A. L. Rheingold, R. H. Crabtree, G. W. Brudvig, Science 1999, 283, 1524.
14. B. B. Keele, J. M. McCord, I. Fridovich, J. Biol. Chem. 1970, 245, 6176.
15. D. Benson, Mechanisms of Oxidation by Metal Ions, Elsevier: New York, 1976.
16. (a) A. Castiñeiras, I. García, E. Bermejo, D. X. West, Z. Naturforsch. 2000, 55 b, 511;
17. (b) A. Castiñeiras, I. García, E. Bermejo, D. X. West, Polyhedron 2000, 19, 1873;
18. (c) I. García-Santos, A. Hagenbach, U. Abram, Dalton Trans. 2004, 677,
19. (d) E. Bermejo, A. Castiñeiras, I. García-Santos, D. X. West, Z. Anorg. Allg. Chem. 2005, 631, 2011;
20. (e) M. C. Aguirre, J. Borrás, A. Castin̈eiras, J. M. García-Monteagudo, I. García-Santos, J. Niclos, D. X. West, Eur. J. Inorg. Chem. 2006, 1231.
21. I. García-Santos, U. Abram, R. Alberto, E. Vázquez López, A. Sánchez, Inorg. Chem. 2004, 43, 1834.
22. U. Abram, A. Castiñeiras, I. García-Santos, R. Rodríguez-Riobó, Eur. J. Inorg. Chem. 2006, 3079.
23. (a) S.-Y. Yang, L.-S. Long, R.-B. Huang, L.-S. Zheng, S. W. Ng, Inorg. Chim. Acta 2005, 358, 1882;
24. (b) H.-P. Xiao, L.-G. Zhu, Inorg. Chem. Comm. 2006, 9, 1125.
25. (a) Y.-Q. Sun, J. Zhang, G.-Y. Yang, Chem. Commun. 2006, 1947;
26. (b) M.-X. Peng, C.-G. Hong, C.-K. Tan, J.-C. Chen, M.-L. Tong, J. Chem. Cryst. 2006, 36, 703.
27. (a) S.-F. Tang, J.-L. Song, J.-G. Mao, Eur. J. Inorg. Chem. 2006, 2011;
28. (b) X.-P. Zhou, D. Li, T. Wu, X. Zhang, Dalton Trans. 2006, 2435.
29. (a) L. Han, X. Bu, Q. Zhang, P. Feng, Inorg. Chem. 2006, 45, 5736;
30. (b) Y.-T. Wang, H.-H. Fan, H.-Z. Wang, X.-M. Chen, Inorg. Chem. 2005, 44, 4148.
31. (a) X. Li, R. Cao, Z. Guo, Y. Wang, X. Zhu, J. Mol. Struc. 2006, 798, 64;
32. (b) J.-P. Zhang, Y.-Y. Lin, X.-C. Huang, X.-M. Chen, Cryst. Growth Des. 2006, 6, 519.
33. B. F. Abrahams, T. A. Hudson, R. Robson, J. Am. Chem. Soc. 2004, 126, 8624.
34. W. J. Geary, Coord. Chem. Rev., 1971, 7, 81.
35. X.-L. Yu, Y.-X Tong, X.-M. Chen, T. C. Wak. J. Chem. Cryst. 1997, 27, 441.
36. V. Veidis, B. Dockum, F. F. Charron jr., W. M. Reiff, Inorg. Chim. Acta 1981, 53, L197.
37. B. W. Dockum, G. A. Eisman, E. H. Witten, W. M. Reiff, Inorg. Chem. 1983, 22, 150.
38. H. Masui, Coord. Chem. Rev. 2001, 219, 957.
39. S. K. Chawla, M. Arora, K. Nättinen, K. Rissanen. Polyhedron 2006, 25, 627.
40. R. Rodriguez-Riobo, PhD Thesis, University of Santiago de Compostela, Spain, 2007.
41. G. Pulvermacher, Chem. Ber. 1894, 27, 613.
42. D. Twomey, J. Org. Chem. 1966, 31, 2494.
43. (a) H.-Z. Shi, Z. L. Li, Y.-K. Shan, Z. Kristallogr. 2005, 220, 245;
44. (b) F. A. Cotton, L. M. Daniels, C. A. Murillo, L. A. Zuñiga, Eur. J. Solid State Inorg. Chem. 1994, 31, 535;
45. (c) H. M. Ali, S. Puvaneswary, S. W. Ng, Acta Crystallogr. 2005, E61, m474.
46. (a) G. De Munno, G. Viau, M. Julve, F. Lloret, J. Faus. Inorg. Chim. Acta. 1997, 257, 121;
47. (b) R. Cortes, M. K. Urtiaga, L. Lezama, J. L. Pizarro, M. I. Arriortua, T. Rojo, Inorg. Chem. 1997, 36, 5016.
48. (a) T. J. Wallace, J. Org. Chem. 1966, 31, 3071;
49. (b) E. W. Ainscough, A. G. Bingham, A. M. Brodie, Inorg. Chim. Acta 1985, 96, L47;
50. (c) E. W. Ainscough, M. L. Brader, A. M. Brodie, G. J. Gainsford, Inorg. Chim. Acta 1991, 180, 81;
51. (d) E. S. Raper, Coord. Chem. Rev. 1994, 129, 91;
52. (e) Y.-M. Zhang, L. Xian, T.-B. Wei, K.-B. Wei, K.-B. Yu, J. Chem. Research S 2003, 798;
53. (f) L. H. van Poppel, T. L. Groy, M. Tyler Caudle, Inorg. Chem. 2004, 43, 3180.
54. X. Shen, X. Shi, B. Kang, Y. Tong, Y. Liu, L. Gu, Q. Liu, Y. Huang, Polyhedron 1999, 18, 33.
55. (a) A. I. Matesanz, I. Cuadrado, C. Pastor, P. Souza, Z. Anorg. Allg. Chem. 2005, 631, 780;
56. (b) P. Gomez-Saiz, J. Garcia-Tojal, V. Diez-Gomez, R. Gil-Garcia, J. L. Pizarro, M. I. Arriortua, T. Rojo, Inorg. Chem. Comm. 2005, 8, 259;
57. (c) P. Gomez-Saiz, R. Gil-Garcia, M. A. Maestro, J. L. Pizarro, M. I. Arriortua, L. Lezama, T. Rojo, J. Garcia-Tojal, Eur. J. Inorg. Chem. 2005, 3409;
58. (d) R. Acharyya, S. Dutta, F. Basuli, S.-M. Peng, G.-H. Lee, L. R. Falvello, S. Bhattacharya, Inorg. Chem. 2006, 45, 1252.
59. L. Shen, Inorg. Chem. Commun. 2003, 6, 1133.
60. B. Ding, L. Yi, P. Cheng, H-B. Song, H-G. Wang, J. Coord. Chem. 2004, 57, 771.
61. D. Zhu, Y. Xu, Y. Mei, Y. Shi, Ch. Tu, X. You, J. Mol. Struct. 2001, 559, 119.
62. S. Ferrer, R. Ballesteros, A. Sambartolome, M. Gonzalez, G. Alzuet, J. Borras, M. Liu, J. Inorg. Biochem. 2004, 98, 1436.
63. Y. Huang, D. W. Stephan, Can. J. Chem. 1995, 73, 956.
64. H.-B. Bürgi, J. D. Dunitz (ed), Structure Correlations, Vol. 2, VCH, Weinheim, 1994.
65. (a) S. Kubota, Y. Ueda, K. Fujikane, K. Toyooka, M. Shibuya, J. Org. Chem. 1980, 45 1473;
66. (b) R. Noto, F. Buccheri, G. Cusmano, M. Gruttadauria, G. Werber. J. Heterocyclic Chem. 1991, 28, 1421;
67. (c) M. Gruttadauria, F. Buccheri, S. Buscemi, G. Cusmano, R. Noto, G. Werber, J. Heterocyclic. Chem. 1992, 29, 233;
68. (d) R. Noto, P. Lo Meo, M. Gruttadauria, G. Werber, J. Heterocyclic. Chem. 1996, 33, 863;
69. (e) S. A. Salim, K. Saleem, M. A. Khan, Indian J. Chem. 1997, 36B, 617;
70. (f) R. Noto, P. Lo Meo, M. Gruttadauria, G. Werber, J. Heterocyclic. Chem. 1999, 36, 667;
71. (g) S. Buscemi, M. Gruttadauri, Tetrahedron 2000, 56, 999;
72. (h) M. A. Martins Alho, R. Baggio, M. T. Garland, N. B. D'Accorso, O. Varela, Carbohydrate Res. 2002, 337, 1397;
73. (i) M. A. Shaban, M. A, Mostafa, A. Z. Nasr, Pharmazie 2003, 58, 367-371;
74. (j) P. Lo Meo, M. Gruttadauria, R. Noto, Arkivoc 2005, 114.
75. A. Castiñeiras, I. Garcia-Santos, S. Dehnen, P. Sevillano, Polyhedron 2006, 25, 3653.
76. (a) K. Nakamoto. Infrared and Raman Spectra of Inorganic and Coordination Compounds. 5th Ed., Wiley, USA, 1997;
77. (b) B. J. Hathaway, A. E. Underhill, J. Chem. Soc., 1961, 3091.
78. A. B. P. Lever, Inorganic Electronic Spectroscopy, 2nd ed., Elsevier Science Publishing Company, Amsterdam, 1984.
79. (a) J. L. Burmeister, F. Basolo, Inorg. Chem. 1964, 3, 1587;
80. (b) A. Sabatini, I. Bertini, Inorg. Chem., 1965, 4, 1665.
81. A. C. T. North, D. C. Phillips, F. S. Mathews, Acta Crystallogr. 1968, A24, 351.
82. Bruker, SMART and SAINT. Area Detector Control Integration Software, Bruker Analytical X-ray Instruments, Inc., Madison, Wisconsin, USA, 1999.
83. G. M. Sheldrick, SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Göttingen, Germany, 1997.
84. G. M. Sheldrick, Acta Crystallogr. 1990, A46, 467.
85. G. M. Sheldrick, SHELX-97. Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
86. A. J. C. Wilson International Tables for Crystallography, Vol. C, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1995.