Enantioselectivity in Ni(II) Schiff-base complexes derived from amino-acids and (S)-o-N-(N-benzylprolyl)aminobenzophenone. Molecular structure of several chiral Ni(II) Schiff-base complexes, circular dichroism and molecular mechanics studies

Dalton Transactions

Volumn , Issue 13, 2005, Pages 2312-2321

  Pessoa, J Costa ^a   Correia, I ^a   Galvao A ^a   Gameiro, A ^a,c   Felix, V ^b   Fiuza, E ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b UNIVERSITY OF AVEIRO   (Portugal)

^c ADDENBROOKE S HOSPITAL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CIRCULAR DICHROISM; DIASTEREOISOMERS; SCHIFF-BASE COMPLEXES; SQUARE-PLANAR COORDINATION;

AMINO ACIDS; AROMATIC COMPOUNDS; CRYSTAL STRUCTURE; ENZYME INHIBITION; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL); THERMODYNAMICS; X RAY DIFFRACTION;

NICKEL;

AMINO ACID; BENZOPHENONE DERIVATIVE; N (N BENZYLPROLYL)AMINOBENZOPHENONE; N-(N-BENZYLPROLYL)AMINOBENZOPHENONE; NICKEL; ORGANOMETALLIC COMPOUND; SCHIFF BASE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; MEDICAL RESEARCH; STEREOISOMERISM; X RAY DIFFRACTION;

AMINO ACIDS; BENZOPHENONES; BIOMEDICAL RESEARCH; CIRCULAR DICHROISM; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; SCHIFF BASES; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 22444434190     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/b503786g     Document Type: Article

References (54)

1. S. C. Stinson, Chem. Eng. News, 1994, 38, 38.
2. Chem. Rev., 2003, 103 (ed. C. Bolm and J. A. Gladysz).
3. Chirality in Industry. The Commercial Manufacture and Applications of Optically Active Compounds, ed. A. N. Collins, G. N. Sheldrake and J. Crosby, John Wiley & Sons, Chichester, 1992.
4. R. M. Williams, Synthesis of Optically Active a-Amino Acids, Pergamon, Oxford, 1989.
5. R. O. Duthaler, Tetrahedron, 1994, 50, 1539-1650.
6. C. Cativiela and M. D. Días-se-Villegas, Tetrahedron: Asymmetry, 1998, 9, 3517-3599.
7. F. P. J. T. Rutjes, L. B. Wolf and H. E. Schoemaker, J. Chem. Soc., Perkin Trans. 1, 2000, 4197-4212.
8. R. M. Williams, Chem. Rev., 1992, 92, 889.
9. D. Seebach, A. R. Sting and M. Hoffman, Angew. Chem., Int. Ed. Engl., 1996, 35, 2708.
10. A. Spatola, Chemistry and Biochemistry of Amino acids, Peptides and Proteins, Marcel Decker, New York, 1983, p. 267.
11. V. A. Soloshonok, V. P. Kukhar, S. V. Galushko, N. Yu Svistunova, D. V. Avilov, N. A. Kuz'mina, N. I. Raevski, Yu. T. Struchkov, A. P. Pysarevsky and Yu. N. Belokon, J. Chem. Soc., Perkin Trans. 1, 1993, 3143-3155.
12. K. Maruoka and T. Ooi, Chem. Rev., 2003, 103, 3013-3028.
13. Yu. N. Belokon, I. E. Zel'tzer, M. G. Ryzhov, M. B. Saporovskaya, V. I. Bakhmutov and V. M. Belikov, J. Chem. Soc., Chem. Commun., 1982, 180-181.
14. Yu. N. Belokon, I. E. Zel'tzer, V. I. Bakhmutov, M. B. Saporovskaya, M. G. Ryzhov, A. I. Yanovsky, Yu. T. Struchkov and V. M. Belikov, J. Am. Chem. Soc., 1983, 105, 2010-2017.
15. Yu. N. Belokon, V. I. Maleyev, S. V. Vitt, M. G. Ryzhov, Yu. D. Kondrashov, S. N. Golubev, Yu. P. Vauchskii, A. I. Kazika, M. I. Novikova, P. A. Krasutskii, A. G. Yurchenko, I. L. Dubchak, V. E. Shklover, Yu. T. Struchkov, V. I. Bakhmutov and V. M. Belikov, J. Chem Soc., Dalton Trans., 1985, 17-26.
16. Yu. N. Belokon, Pure Appl. Chem., 1992, 64, 1917-1924.
17. Yu. N. Belokon, Bull. RUSS. Acad. Sci., 1993, 41, 868-884.
18. M. G. Ryzhov and Yu. N. Belokon, Russ. J. Appl. Chem., 1994, 67, 101-104.
19. V. A. Soloshonok, D. V. Avilov, V. P. Kukhar, V. I. Taravorov, T. F. Savel'eva, T. D. Churkina, N. S. Ikonnikov, K. A. Kochetkov, S. A. Orlova, A. P. Pysarevsky, Yu. T. Struchkov, N. I. Raevski and Yu. N. Belokon, Tetrahedron: Asymmetry, 1995, 6, 1741-1756.
20. J. Jirman and A. Popkov, Collect. Czech. Chem. Commun., 1995, 60, 990-998.
21. Yu. N. Belokon, N. B. Bespalova, T. D. Churkina, I. Cisarová, M. G. Ezernitskaya, S. R. Harutyunyan, R. Hrdidina, H. B. Kagan, P. Kocovsky, K. A. Kochetkov, O. V. Larionov, K. A. Lyssenko, M. North, M. Polásek, A. S. Peregudov, V. V. Prisyazhnyuk and S. Vyskocil, J. Am. Chem. Soc., 2003, 125, 12860-12871.
22. A. S. Saghiyan, A. V. Geolchanyan, S. M. Djamgaryan, S. M. Vardapetyan, V. I. Tararov, N. A. Kuz'mina, N. S. Ikonnikov, Yu. N. Belokon and M. North, Russ. Chem. Bull., Int. Ed., 2000, 49, 1460-1463.
23. A. S. Saghiyan, A. V. Geolchanyan, L. L. Manasyan, G. M. Mkrtchyan, N. R. Martirosyan, S. A. Dadayan, T. V. Kochickyan, S. R. Harutyunyan, A. A. Avetisyan, V. I. Tararov, V. Maleev and Yu. N. Belokon, Russ. Chem. Bull., Int. Ed., 2004, 53, 932-935.
24. A. S. Saghiyan, A. V. Geolchanyan, S. G. Petrosyan, T. V. Ghochikyan, V. S. Haroutunyan, A. A. Avetisyan, Yu. N. Belokon and K. Fisher, Tetrahedron: Asymmetry, 2004, 15, 705-711.
25. R. N. Krasikova, V. V. Zaitsev, S. M. Ametamey, O. F. Kuznetsova, O. S. Fedorova, I. K. Mosevich, Yu. N. Belokon, S. Vyskocil, S. V. Shatik, M. Nader and P. A. Schubinger, Nucl. Med. Biol, 2004, 31, 597-603.
26. Yu. N. Belokon, S. R. Harutyunyan, E. V. Vorontsov, A. S. Peregudov, V. N. Chrustalev, K. A. Kochetkov, D. Pripadchev, A. S. Sagyan, A. K. Beck and D. Seebach, ARKIVOC, 2004, iii, 132-150.
27. Yu. N. Belokon, A. S. Sagyan, S. M. Djamgaryan, V. I. Bakhmutov and V. M. Belikov, Tetrahedron, 1988, 44, 5507-5514.
28. Yu. N. Belokon, A. G. Bulychev, S. V. Vitt, Yu. T. Struchkov, A. S. Batsanov, T. V. Timofeeva, V. A. Tsyryapkin, M. G. Ryzhov, L. A. Lysova, V. I. Bakhmutov and V. M. Belikov, J. Am. Chem. Soc., 1985, 107, 4252-4259.
29. S. V. Lindeman, T. V. Timofeeva, V. I. Maleyev, Yu. N. Belokon, M. G. Ryzhov, V. M. Belikov and Yu. T. Struchkov, Acta Crystallogr., Sect. C, 1985,41, 1290-1295.
30. Yu. N. Belokon, A. G. Bulychev, M. G. Ryzhov, S. V. Vitt, A. S. Batsanov, Yu. T. Struchkov, V. I. Bakhmutov and V. M. Belikov, J. Chem. Soc., Perkin Trans. 1, 1986, 1865-1872.
31. C. J. Hawkins, Absolute Configuration of Metal Complexes; Wiley-Interscience, New York, 1971, pp. 8-15.
32. Yu. N. Belokon, A. S. Sagyan, A. A. Djamgaryan, V. I. Bakhmutov, S. V. Vitt, A. S. Batsanov, Yu. T. Struchkov and V. M. Belikov, J. Chem. Soc., Perkin Trans. 1, 1990, 2301-2310.
33. A. K. Rappé, C. J. Casewit, K. S. Colwell, W. A. Goddard, III and W. M. Skiff, J. Am. Chem. Soc., 1992, 114, 10024.
34. CERIUS 2 (v3.5), San Diego, Molecular Simulations Inc., 1997.
35. P. Comba, Coord. Chem. Rev., 1999, 182, 343-371.
36. P. Comba and T. W. Hambley, Molecular Modeling of Inorganic Compounds, Wiley-VCH, Weinheim, 1995.
37. A. B. P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, 1984, pp. 534-544.
38. Y. Nishida and S. Kida, Coord. Chem. Rev., 1979, 27, 275-298.
39. Y. Nishida and S. Kida, Bull. Chem. Soc. Jpn., 1970, 43, 3814.
40. B. J. Bosnich, J. Am. Chem. Soc., 1968, 90, 627-632.
41. R. Kuroda and Y. Saito, Circular Dichroism of Inorganic Complexes: Interpretation and Application, in Circular Dichroism Principles and Applications, ed. K. Nakanishi, N. Berova and R. W Woody, VCH, New York, 1994, pp. 217-258.
42. Yu. N. Belokon, V. I. Bakhmutov, N. I. Chernoglazova, K. A. Kochetkov, S. V. Vitt, N. S. Garbalinskaya and V. M. Belikov, J. Chem. Soc., Perkin Trans. 1, 1988, 305-312.
43. J. P. Costes, J. M. Dominguez-Vera and J. P. Laurent, Polyhedron, 1995, 14, 2179-2187.
44. R. S. Downing and F. L. Urbach, J. Am. Chem. Soc., 1970, 92, 5861-5865.
45. N. C. Payne, Inorg. Chem., 1973, 12, 1151-1156.
46. K. Okazaki and K. Saito, Bull. Chem. Soc. Jpn., 1982, 55, 785-791.
47. A. Wojtczak, E. Szlyk, M. Jaskóski and E. Larsen, Acta Chem. Scand., 1997, 51, 274-278.
48. J. W. Chang and R. B. Martin, J. Phys. Chem., 1969, 73, 4277-4283.
49. I. Cavaco, J. Costa Pessoa, D. Costa, M. T. L. Duarte, R. D. Gillard and P. M. Matias, J. Chem. Soc., Dalton Trans., 1994, 149-157.
50. C. K. Fair, MOLEN, Enraf-Nonius, Delft, 1990.
51. G. M. Sheldrick, SHELXS 86, Program for the Solution of Crystal Structure, University of Gottingen, 1986.
52. G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structure (release 97-2), University of Gottingen, 1997.
53. L. J. Farrugia, Ortep-3 for Windows, J. Appl. Crystallogr., 1997, 30, 565.
54. L. J. Farrugia, WingX (vl.64.03b), J. Appl. Crystallogr., 2002, 32, 837-838.