Ridge-tile-like chiral topology: Synthesis, resolution, and complete chiroptical characterization of enantiomers of edge-sharing binuclear square planar complexes of Ni(II) bearing achiral ligands

Journal of the American Chemical Society

Volumn 132, Issue 30, 2010, Pages 10477-10483

  Soloshonok, Vadim A ^a   Ono, Taizo ^b   Ueki, Hisanori ^c   Vanthuyne, Nicolas ^d   Balaban, Teodor Silviu ^d,e   Bürck, Jochen ^e   Fliegl, Heike ^e   Klopper, Wim ^e   Naubron, Jean Valère ^d   Bui, Tam T T ^f   Drake, Alex F ^f   Roussel, Christian ^d  

^a INSTITUTE OF HYDROBIOLOGY   (Ukraine)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^c NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^d AIX MARSEILLE UNIVERSITÉ   (France)

^e KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^f KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ACHIRAL LIGANDS; CHIRAL COMPOUNDS; CHIRAL STATIONARY PHASE; CHIRAL TOPOLOGY; CHIROPTICAL PROPERTIES; CONFIGURATIONALLY; EDGE SHARING; NI COMPLEXES; NICKEL ATOMS; SQUARE PLANAR COMPLEX; THEORETICAL CALCULATIONS; TRIDENTATE LIGANDS;

CHELATION; ENANTIOMERS; ETHANOL; SANDWICH STRUCTURES; TOPOLOGY;

LIGANDS;

ALCOHOL; IMINE; NICKEL; NITROGEN;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHYSICAL CHEMISTRY; SYNTHESIS;

CRYSTALLOGRAPHY, X-RAY; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NICKEL; STEREOISOMERISM;

EID: 77955026353     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103296g     Document Type: Article

References (47)

1. Aullón, G., Ujaque, G., Lledos, A., Alvarez, S., and Alemany, P. Inorg. Chem. 1998, 37, 804-813
2. Aullón, G., Lledos, A., and Alvarez, S. Inorg. Chem. 2000, 39, 906-916
3. Aullón, G., Ujaque, G., Lledos, A., and Alvarez, S. Chem.-Eur. J. 1999, 5, 1391-1410
4. Marshall, W. J., Aullón, G., Alvarez, S., Dobbs, K. D., and Grushin, V. V. Eur. J. Inorg. Chem. 2006, 3340-3345
5. Mizuta, T., Aoki, S., Nakayama, K., and Miyoshi, K. Inorg. Chem. 1999, 38, 4361-4364
6. Aullón, G. and Alvarez, S. Inorg. Chem. 2001, 40, 4937-4946
7. Lasri, J., Kopylovich, M. N., Guedes da Silva, M. F. C., Charmier, M. A. J., and Pombeiro, A. J. L. Chem.-Eur. J. 2008, 14, 9312-9322
8. Azerraf, C., Cohen, S., and Gelman, D. Inorg. Chem. 2006, 45, 7010-7017
9. For examples of roof shape binuclear Ni complexes with additional chirality coming from chiral ligand, see: Brunner, H., Dormeier, S., Grau, I., and Zabel, M. Eur. J. Inorg. Chem. 2002, 2603-2613
10. Duran, J., Polo, A., Real, J., Benet-Buchholz, J., Poater, A., and Sola, M. Eur. J. Inorg. Chem. 2003, 4147-4151
11. Soloshonok, V. A. and Ueki, H. J. Am. Chem. Soc. 2007, 129, 2426-2427
12. Piras, P. and Roussel, C. J. Pharm. Biomed. Anal. 2008, 46, 839-847
13. For some recent semi-preparative separations of metal complexes on chiral support, see
14. Norel, L., Rudolph, M., Vanthuyne, N., Williams, J. A. G., Lescop, C., Roussel, C., Autschbach, J., Crassous, J., and Reau, R. Angew. Chem., Int. Ed. 2010, 49, 99-102
15. Setsune, J.-I., Tsukajima, A., Okasaki, N., Lintuluoto, J. M., and Lintuluoto, M. Angew. Chem., Int. Ed. 2009, 48, 771-775
16. Lai, R., Chanon, F., Roussel, C., Sanz, M., Vanthuyne, N., and Daran, J.-C. J. Organomet. Chem. 2008, 693, 23-32
17. Rang, A., Engeser, M., Maier, N. M., Nieger, M., Lindner, W., and Schalley, C. A. Chem.-Eur. J. 2008, 14, 3855-3859
18. Sun, P., Krishnan, A., Yadav, A., Singh, S., MacDonnell, F. M., and Armstrong, D. W. Inorg. Chem. 2007, 46, 10312-10320
19. Warnke, M. M., Cotton, F. A., and Armstrong, D. W. Chirality 2007, 19, 179-183
20. Chen, X., Okamoto, Y., Yano, T., and Otsuki, J. J. Sep. Sci. 2007, 30, 713-716
21. Lassen, P. R., Guy, L., Karame, I., Roisnel, T., Vanthuyne, N., Roussel, C., Cao, X., Lombardi, R., Crassous, J., Freedman, T. B., and Nafie, L. A. Inorg. Chem. 2006, 45, 10230-10239
22. Paisner, S. N. and Bergman, R. G. J. Organomet. Chem. 2001, 621, 242-245
23. Ciclosi, M., Lloret, J., Estevan, F., Lahuerta, P., Sanau, M., and Pérez-Prieto, J. Angew. Chem., Int. Ed. 2006, 45, 6742-6744
24. For exchange processes on the chiral column, see: Schurig, V. J. Chromatogr., A 2009, 1216, 1723-1736
25. Wolf, C. Chem. Soc. Rev. 2005, 34, 595-608
26. Trapp, O. Anal. Chem. 2006, 78, 189-198
27. Trapp, O. Chirality 2006, 18, 489-497
28. Vanthuyne, N., Andreoli, F., Fernandez, S., Roman, M., and Roussel, C. Lett. Org. Chem. 2005, 2, 433-443
29. Roussel, C., Vanthuyne, N., Bouchekara, M., Djafri, A., Elguero, J., and Alkorta, I. J. Org. Chem. 2008, 73, 403-411
30. Review: Roussel, C., Del Rio, A., Pierrot-Sanders, J., Piras, P., and Vanthuyne, N. J. Chromatogr., A 2004, 1037, 311-3
31. Roussel, C., Vanthuyne, N., Serradeil-Albalat, M., and Vallejos, J.-C. J. Chromatogr., A 2003, 995, 79-85
32. Ahlrichs, R., Bär, M., Horn, H., and Kölmel, C. Chem. Phys. Lett. 1989, 162, 165-169
33. Slater, J. C. Phys. Rev. 1951, 81, 385-390
34. Vosko, S. H., Wilk, L., and Nusair, M. Can. J. Phys. 1980, 58, 1200-1211
35. Lee, C., Yang, W., and Parr, R. G. Phys. Rev. 1988, B37, 785-789
36. Becke, A. D. Phys. Rev. 1988, A38, 3098-3100
37. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
38. Stephens, P. J., Devlin, F. J., Chablowski, C. F., and Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
39. Weigend, F. and Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297-3305
40. Furche, F. and Rappoport, D. Density functional methods for excited states: equilibrium structure and electronic spectra. In Computational Photochemistry; Olivucci, M., Ed.; Elsevier: Amsterdam, 2005; Vol. 16, Chapter III.
41. Bauernschmitt, R. and Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454-464
42. Treutler, O. and Ahlrichs, R. J. Chem. Phys. 1995, 102, 346-354
43. Frisch, M. J.; et al. Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
44. Wolf, C. Racemization, enantiomerization and diastereomerization. Dynamic Stereochemistry of Chiral Compounds, Principles and Applications; RCS Publishing: Cambridge, UK, 2008; Chapter III.
45. Maskill, H. The Physical Basis of Organic Chemistry; Oxford University Press: Oxford, 1985.
46. -1) was estimated from three available experimental points, which were perfectly aligned. This is not sufficient for a precise determination of the barrier; however, it provides evidence that the barrier is qualitatively higher in 1 than in 2 and 3.
47. 1/2 = 11 min at 15 °C in EtOH). The tridendate nature of the ligand and the high basicity and steric bulk of the tertiary amine are the basis for the reasonable configurational stability observed in 1, 2, 3, and 4.