Reassignment, isolation, spectral and x-ray characterization of diastereoisomers of the macrocyclic ligand 3,10-meso-3,5,7,7,10,12,14,14- octamethyl-1,4,8,11-tetraazacyclotetradecane and their NiII and CuII complexes

European Journal of Inorganic Chemistry

Volumn , Issue 5, 2006, Pages 994-1005

  Lin, Yung Chan ^a   Misra, Tarun Kumar ^b   Lu, Tian Huey ^c   Joseph, Maddirala Shambabu ^c   Chung, Chung Sun ^c  

^a INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^c NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

Coordination modes; Diastereoisomers; Macrocyclic ligands; X ray crystallography

Indexed keywords

CHLORINE COMPOUNDS; COPPER COMPOUNDS; LIGANDS; MOLECULES; NICKEL COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SELF ASSEMBLY; SODIUM BOROHYDRIDE; STEREOCHEMISTRY;

% REDUCTIONS; COORDINATION MODES; DIASTEREOISOMERS; MACRO-CYCLIC LIGANDS; MACROCYCLES; METHYL GROUP; SODIUM BORO HYDRIDES; SODIUM BOROHYDRIDES; UV/ VIS SPECTROSCOPY; X-RAY CHARACTERIZATION;

X RAY CRYSTALLOGRAPHY;

EID: 33644999122     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200500889     Document Type: Article

References (66)

1. a) M. Shionoya, E. Kimura, Y. Iitaka, J. Am. Chem. Soc. 1990, 112, 9237-9245 and references cited therein;
2. b) G. J. Bridger, R. T. Skerlj, S. Padmanabhan, D. Thornton, J. Org. Chem. 1996, 61, 1519-1522;
3. c) X. Liang, J. A. Parkinson, M. Weishaupl, R. O. Gould, S. J. Paisey, H.-S. Park, T. M. Hunter, C. A. Blindauer, S. Parsons, P. J. Sadler, J. Am. Chem. Soc. 2002, 124, 9105-9112;
4. d) J. Larionova, R. Clérac, B. Donnadieu, S. Willemin, C. Guérin, Cryst. Growth Des. 2003, 3, 267-272;
5. e) E. Colacio, I. B. Maimoun, F. Lloret, J. Suārez-Varela, Inorg. Chem. 2005, 44, 3771-3773;
6. f) O. Enoki, T. Imaoka, K. Yamamoto, Org. Lett. 2003, 5, 2547-2549;
7. g) T. K. Misra, C.-S. Chung, J. Cheng, T.-H. Lu, Polyhedron 2001, 20, 3149-3154.
8. a) B. Konig, M. Pelka, H. Zieg, P. G. Jones, I. Dix, Chem. Commun. 1996, 471-472;
9. b) S. Aime, M. Botta, S. G. Crich, G. B. Giovenzana, G. Jommi, R. Pagliarin, M. Sisti, J. Chem. Soc., Chem. Commun. 1995, 1885-1886;
10. c) T. J. Norman, D. Parker, F. C. Smith, D. J. King, J. Chem. Soc., Chem. Commun. 1995, 1879-1880.
11. E. K. Barefield, G. M. Freeman, D. G. Van Derveer, Inorg. Chem. 1986, 25, 552-558.
12. a) D. J. Szalda, E. Fujita, R. Sanzenbacher, H. Paulus, H. Elias, Inorg. Chem. 1994, 33, 5855-5863 and references cited therein;
13. b) E. Kimura, M. Haruta, T. Koike, M. Shionoya, K. Takenouchi, Y. Iitaka, Inorg. Chem. 1993, 32, 2779-2784.
14. a) B. Bosnich, C. K. Poon, T. Tobe, Inorg. Chem. 1965, 4, 1102-1108;
15. b) J.-W. Chen, C.-S. Chung, Inorg. Chem. 1986, 25, 2841-2846;
16. c) R. W. Hay, R. Bembi, D. A. House, J. Chem. Soc., Dalton Trans. 1984, 1921-1925.
17. a) N. F. Curtis, D. A. Swan, T. N. Waters, I. E. Maxwell, J. Am. Chem. Soc. 1969, 91, 4588-4589;
18. b) T. Ito, D. H. Busch, Inorg. Chem. 1974, 13, 1770-1772.
19. D. A. Swan, T. N. Waters, N. F. Curtis, J. Chem. Soc., Dalton Trans. 1972, 1115-1120.
20. R. Bembi, S. M. Sondhi, A. K. Singh, A. K. Jhanji, T. G. Roy, J. W. Lown, R. G. Ball, Bull. Chem. Soc. Jpn. 1989, 62, 3701-3705.
21. a) G. Ferguson, A. J. Lough, Acta Crystallogr., Sect. C 1990, 46, 213-215;
22. b) R. Bembi, T. G. Roy, A. K. Jhanji, A. J. Maheswari, Chem. Soc., Dalton Trans. 1990, 3531-3534;
23. c) R. Bembi, M. G. B. Drew, R. Singh, T. G. Roy, Inorg. Chem. 1991, 30, 1403-1406;
24. d) S. K. S. Hazari, T. G. Roy, B. K. Dey, S. C. Das, E. R. T. Tiekink, Metal-Based Drugs 1997, 4, 255-265;
25. e) R. W. Hay, I. Fraser, Polyhedron 1998, 17, 1931-1936;
26. f) K.-Y. Choi, K. M. Chun, I.-H. Suh, Inorg. Chem. Commun. 1999, 2, 210-213;
27. g) K.-Y. Choi, I.-H. Suh, Main Group Met. Chem. 1999, 22, 123-126;
28. h) S.-G. Kang, J. Song, J. H. Jeong, Inorg. Chim. Acta 2000, 310, 196-202;
29. i) T. G. Roy, R. Bembi, S. K. S. Hazari, B. K. Dey, T. K. Acharjee, E. Horn, E. R. T. Tiekink, J. Coord. Chem. 2002, 55, 853-862;
30. j) S.-G. Kang, K. Ryu, J. Kim, Bull. Korean Chem. Soc. 2002, 23, 81-85;
31. k) T. G. Roy, J. Bangl. Chem. Soc. 2002, 15, 23-29;
32. l) T.-J. Lee, T.-Y. Lee, W.-B. Juang, C.-S. Chung, Acta Crystallogr., Sect. C 1985, C41, 1596-1598;
33. m) S. K. S. Hazari, T. G. Roy, B. K. Dey, H. A. Miah, S. Dutta, E. R. T. Tiekink, Z. Kristallogr. New Cryst. Struct. 2001, 216, 441-442.
34. a) A. K. Singh, A. Kumar, S. Panwar, S. Baniwal, Analyst 1999, 124, 521-525;
35. b) K. Kimura and T. Shono, Cation Binding by Macrocycles. Complexation of Cationic Species by Crown Ethers (Eds.: Y. Inoue, G. W. Gokel), Marcel Dekker, New York, 1990, p. 429;
36. c) H. Tsukube, Talanta 1993, 40, 1313-1324.
37. T. G. Roy, S. K. Hazari, b. K. Dey, H. A. Miah, C. Bader, D. Rehder, Eur. J. Inorg. Chem. 2004, 4115-4123.
38. S. Seiji, T. C. Bruice, J. Am. Chem. Soc. 1973, 95, 7528-7530.
39. G. H. Searle, R. W. Hay, B. Jeragh, Aust. J. Chem. 1980, 33, 1447-1461.
40. Y. Hung, L. Y. Martin, S. C. Jackels, A. M. Tait, D. H. Busch, J. Am. Chem. Soc. 1977, 99, 4029-4039.
41. R. W. Hay, M. P. Pujari, Inorg. Chim. Acta 1985, 99, 75-79.
42. S.-G. Kang, J. Song, Bull. Korean Chem. Soc. 2000, 21, 1106-1110.
43. T. Ito, H. Ito, K. Toriumi, Acta Crystallogr., Sect. B 1981, 37, 1412-1415.
44. T.-J. Lee, T.-H. Lu, C.-S. Chung, T.-Y. Lee, Acta Crystallogr., Sect. C 1984, 40, 70-72.
45. a) T.-H. Lu, S.-C. Lin, H. Aneetha, K. Panneerselvam, C.-S. Chung, J. Chem. Soc., Dalton Trans. 1999, 3385-3391;
46. b) K. Panneerselvam, T.-H. Lu, T.-Y. Chi, S.-F. Tung, C.-S. Chung, Acta Crystallogr., Sect. C 2000, 56, 301-302.
47. a) K. Panneerselvam, T.-H. Lu, S.-F. Tung, T.-Y. Chi, C.-S. Chung, Anal. Sci. 1998, 14, 1029-1030;
48. b) K. Panneerselvam, T.-H. Lu, T.-Y. Chi, F.-L. Liao, C.-S. Chung, Anal. Sci. 2000, 16, 439-440.
49. a) J. R. Röper, H. Elias, Inorg. Chem. 1992, 31, 1210-1214;
50. b) N. Jubran, D. Meyerstein, J. Koresh, H. Cohen, J. Chem. Soc., Dalton Trans. 1986, 2509-2513.
51. a) L. Sabatini, L. Fabbrizzi, Inorg. Chem. 1979, 18, 438-444;
52. b) L. Fabbrizzi, M. Micheloni, P. Paoletti, J. Chem. Soc., Dalton Trans. 1980, 134-136;
53. c) Y.-C. Lin, T. K. Misra, P.-S. Wang, C.-S. Chung, Inorg. Chim. Acta 2005, 358, 1777-1784.
54. a) L. Fabbrizzi, Inorg. Chim. Acta 1977, 24, L21-L23;
55. b) L. Fabbrizzi, J. Chem. Soc., Dalton Trans. 1979, 1857-1861.
56. a) M. Ciampolini, L. Fabbrizzi, M. Liccheli, F. Perotti, F. Pezzini, A. Poggi, Inorg. Chem. 1986, 25, 4131-4135;
57. b) R. W. Hay, B. Jeragh, G. Ferguson, B. Kaitner, B. L. Ruhl, J. Chem. Soc., Dalton Trans. 1982, 1531-1539.
58. R. W. Hay, B. Kinsman, C. I. Smith, Polyhedron 1995, 14, 1245-1249.
59. a) A. B. O. Lever, Inorganic Electronic Spectroscopy, American Elsevier, New York, N. Y., 1984, pp 355, 554-572;
60. b) J. C. Kim, J. C. Fettinger, Y. I. Kim, Inorg. Chim. Acta 1999, 286, 67-73;
61. c) T. M. Donlevy, L. R. Gahan, T. W. Hambley, G. R. Hanson, K. L. McMahon, R. Stranger, Inorg. Chem. 1994, 33, 5131-5137;
62. d) J.-W. Chen, C.-S. Chung, Inorg. Chem. 1986, 25, 2841-2846.
63. a) G. M. Sheldrick, SHELXTL PLUS, Siemens Analytical X-ray Instruments Inc., Madison, WI, 1990;
64. b) A. C. T. North, D. C. Phillips, F. S. Mathews, Acta Crystallogr., Sect. A 1968, 24, 351-359.
65. a) G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473;
66. b) G. M. Sheldrick, SHELXL 97, Program for Refinement of Crystal Structures, University of Göttingen, 1997.