X-ray structures of chiral (salen)manganese(III) complexes: Proof of pliability of the salen ligand

Chemistry Letters

Volumn , Issue 10, 1998, Pages 1041-1042

  Irie, Ryo ^a   Hashihayata, Takashi ^a   Katsuki, Tsutomu ^a   Akita, Munetaka ^b   Moro Oka, Yoshihiko ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032270206     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.1041     Document Type: Article

References (25)

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4. K. Srinivasan, P. Michaud, and J. K. Kochi, J. Am. Chem. Soc., 108, 2309 (1986).
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10. a) M. T. Rispens, A. Meetsina, and B. L. Feringa, Recl. Trav. Chim. Pays-Bas., 113, 413 (1994).
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13. a) T. Hamada, T. Fukuda, H. Imanishi, and T. Katsuki, Tetrahedron, 52, 515 (1996).
14. b) Y. Noguchi, R. Irie, T. Fukuda, and T. Katsuki, Tetrahedron Lett., 37, 4533 (1996).
15. c) T. Hashihayata, Y. N. Ito, and T. Katsuki, Synlett, 1996, 1079.
16. d) Y. N. Ito and T. Katsuki, Tetrahedron Lett., 39, 4325 (1998).
17. 5OH: H, 4.98; C, 71.22; N, 2.31%.
18. -1, R1 = 0.067, wR2 = 0.170 for 14516 reflections and 1705 variables, GOF = 1.24. Data were collected on a Rigaku RAXIS-IV imaging plate area detector with graphite monochromated Mo-Kα at -60°C. Structural analysis was performed using the teXsan crystallographic software package. The structure was solved by the direct methods (SHELXS-86) and all non-hydrogen atoms were refined anisotropically (on F2) using SHELXL-97 linked to teXsan.
19. CH-π interaction between the phenyl ring (pointed by arrow 1 or 3) and the neighboring naphthyl group (by arrow 2 or 4) may stabilize this conformation. M. Nishio and M. Hirota, Tetrahedron, 45, 7201 (1989). W. L. Jorgensen and D. L. Severance, J. Am. Chem. Soc., 112, 4768 (1990).
20. CH-π interaction between the phenyl ring (pointed by arrow 1 or 3) and the neighboring naphthyl group (by arrow 2 or 4) may stabilize this conformation. M. Nishio and M. Hirota, Tetrahedron, 45, 7201 (1989). W. L. Jorgensen and D. L. Severance, J. Am. Chem. Soc., 112, 4768 (1990).
21. The coordination squares in 2 and 3 are slightly twisted as indicated by the dihedral angles between the planes defined by the atoms (N, Mn, N) and (O, Mn, O), 3 in 2 and 7 in 3. The degree of the non-planarity of salen ligands is indicated by the dihedral angles between the mean planes [defined by atoms (N,C9,C1, C2,O) and by (N,C9′,C1′,C2′,O)] and the plane [defined by atoms (N,N,O,O)]. The dihedral angles in 2 are ca. 9° and 6°, and those in 3 are ca. 13° and 7°, respectively. These values reflect the twisted coordination squares described above.
22. The analysis of the X-ray structures of Mn-and Cr-salen complexes taken from Cambridge Crystallographic database suggests that the five-membered chelate rings of some salen ligands take envelope-like conformation and also force their basal ligands to take stepped conformation. For example, see reference 5a and a) K. Srinivasan and J. K. Kochi, Inorg. Chem., 24, 4671 (1985).
23. b) J. D. Bois, J. Hong, E. M. Carreira, and M. W. Day, J. Am. Chem. Soc., 118, 915 (1996).
24. equatorial bonds is small. The lengths of M-N bonds are ca. 1.98 Å [cationic Cr(V)], ca. 1.98 A [Cr(V)-pyridine N-oxide adduct], and ca. 1.94 Å [nitrido Mn(V)] (references 11a and 11b).
25. equatorial bonds, this simply means that the syn-periplanar orientation is thermodynamically the most stable, probably due to the favorable CH-π interactions.