Abstract
Complexes of N,N′,N′′-tris(2-hydroxypropyl)-1,4,7-triazacyclononane (L), [CuL](ClO4)(NO3) (1), [CoL](ClO4)2 (2), [ZnL](ClO4)2 (3) and [MnL](ClO4)2 (4), have been synthesized and characterized on the basis of elemental analysis, electrospray ionization mass spectrometry, UV–Vis measurements and cyclic voltammetry. Crystal structures of the former three complexes, characterized by X-ray crystallography, show that these complexes are monoclinic with space group P21/n and P21/c. Each metal central in the complexes is six-coordinate with three N atoms of the macrocycle and three O atoms from the pendant hydroxypropyl arms, forming a distorted octahedral configuration. [MnL](ClO4)2 (4) is employed as catalyst in olefin epoxidation with H2O2. The final results indicate that complex (4) has good catalytic activity towards olefin epoxidation. Under mild conditions, the olefin conversion is moderate and epoxidation selectivity is 95–100%.
Similar content being viewed by others
References
(a) D.H.R. Barton, W.G. Li and J.A. Smith, Tetrahedron Lett., 39, 7055 (1998); (b) R.W. Hay, T. Clifford and N. Govan, Transition Metal. Chem., 23, 619 (1998); (c) J. Brinksma, R. La Crois, B.L. Feringa, M.I. Donnoli and C. Rosini, Tetrahedron Lett., 42, 4049 (2001); (d) J.E. Barker and T. Ren, Tetrahedron Lett., 45, 4681 (2004); (e) J.E. Barker and T. Ren, Tetrahedron Lett., 46, 6805 (2005); (f) J.R.L. Smith, J. Murray, P.H. Walton and T.R. Lowdon, Tetrahedron Lett., 47, 2005 (2006)
(a) J.R.L. Smith and G.B. Shul’pin, Tetrahedron Lett., 39, 4909 (1998); (b) G.V. Nizova, C. Bolm, S. Ceccarelli, C. Pavan and G.B. Shul’pin, Adv. Synth. Catal., 344, 899 (2002); (c) G.B. Shul’pin, G.V. Nizova, Y.N. Kozlov, L.G. Cuervo and G. Süss-Fink, Adv. Synth. Catal., 346, 317 (2004); (d) G. Süss-Fink, L.G. Cuervo, B. Therrien, H. Stoeckli-Evans and G.B. Shul’pin, Inorg. Chim. Acta, 357, 475 (2004); (e) G.B. Shul’pin, G.V. Nizova, Y.N. Kozlov, V.S. Arutyunov, A.C.M. dos Santos, A.C.T. Ferreira and D. Mandelli, J. Organometal. Chem., 690, 4498 (2005)
(a) T.H. Bennur, S. Sabne, S.S. Deshpande, D. Srinivas and S. Sivasanker, J. Mol. Catal. A: Chem., 185, 71 (2002); (b) T.H. Bennur, D. Srinivas, S. Sivasanker and V.G. Puranik, J. Mol. Catal. A: Chem., 219, 209 (2004); (c) T.H. Bennur, D. Srinivas and S. Sivasanker, J. Mol. Catal. A: Chem., 207, 163 (2004)
(a) C. Zondervan, R. Hage and B.L. Feringa, Chem. Commun., 419 (1997); (b) V.B. Romakh, B. Therrien, L. Karmazin-Brelot, G. Labat, H. Stoeckli-Evans, G.B. Shul’pin and G. Süss-Fink, Inorg. Chim. Acta, 359, 1619 (2006)
(a) B.C. Gilbert, N.W.J. Kamp, J.R.L. Smith and J. Oakes, J. Chem. Soc., Perkin Trans.2, 2161 (1997); (b) B.C. Gilbert, N.W.J. Kamp, J.R.L. Smith and J. Oakes, J. Chem. Soc., Perkin Trans. 2, 1841 (1998); (c) B.C. Gilbert, J.R.L. Smith, A.M. Payeras and J. Oakes, Org. Biomol. Chem., 2, 1176 (2004)
B.C. Gilbert J.R.L. Smith M.S. Newton J. Oakes R.P. Prats (2003) Org. Biomol. Chem. 1 1568 Occurrence Handle10.1039/b301026k Occurrence Handle1:CAS:528:DC%2BD3sXkvFSnsLo%3D
(a) R. Hage, J.E. Iburg, J. Kerschner, J.H. Koek, E.L.M. Lempers, R.J. Martens, U.S. Racherla, S.W. Russell, T. Swarthoff, M.R.P. van Vliet, J.B. Warnaar, L. van der Wolf and B. Krijnen, Nature, 369, 637 (1994); (b) V.C. Quee-Smith, L. DelPizzo, S.H. Jureller and J.L. Kerschner, Inorg. Chem., 35, 6461 (1996); (c) D. De Vos and T. Bein, Chem. Commun., 917 (1996); (d) D.E. De Vos and T. Bein, J. Organomet. Chem., 520, 195 (1996); (e) J.H. Koek, E.W.M.J. Kohlen, S.W. Russell, L. van der Wolf, P.F. ter Steeg and J.C. Hellemons, Inorg. Chim. Acta, 295, 189 (1999); (f) D.E. De Vos, B.F. Sels, M. Reynaers, Y.V.S. Rao and P.A. Jacobs, Tetrahedron Lett., 39, 3221 (1998); (g) A. Berkessel and C.A. Sklorz, Tetrahedron Lett., 40, 7965 (1999); (h) G.B. Shul’pin, G. Süss-Fink and J.R. Lindsay-Smith, Tetrahedron, 55, 5345 (1999); (i) G.B. Shul’pin, G. Süss-Fink and L.S. Shul’pina, J. Mol. Catal. A: Chem., 170, 17 (2001); (j) J. Brinksma, L. Schmieder, G. van Vliet, R. Boaron, R. Hage, D. De Vos, P.L. Alsters and B.L. Feringa, Tetrahedron Lett., 43, 2619 (2002); (k) G.B. Shul’pin, G.V. Nizova, Y.N. Kozlov, V.S. Arutyunov, A.C.M. dos Santos, A.C.T. Ferreira and D. Mandelli, J. Organomet. Chem., 690, 4498 (2005)
W.P. Yip W.Y. Yu N. Zhu C.M. Che (2005) J. Am. Chem. Soc. 127 14239 Occurrence Handle10.1021/ja0528230 Occurrence Handle1:CAS:528:DC%2BD2MXhtVequrjP
(a) H. Higashimura, K. Fujisawa, Y. Moro-oka, M. Kubota, A. Shiga, A. Terahara, H. Uyama and S. Kobayashi, J. Am. Chem. Soc., 120, 8529 (1998); (b) H. Higashimura, K. Fujisawa, Y. Moro-oka, M. Kubota, A. Shiga, H. Uyama and S. Kobayashi, J. Mol. Catal. A: Chem., 155, 201 (2000)
(a) J.N. Burstyn and K.A. Deal, Inorg. Chem., 32, 3585 (1993); (b) D. Wahnon, A.M. Lebuis and J. Chin, Angew. Chem. Int. Ed. Engl., 34, 2412 (1995); (c) K.A. Deal, A.C. Hengge and J.N. Burstyn, J. Am. Chem. Soc., 118, 1713 (1996); (d) K.A. Deal and J.N. Burstyn, Inorg. Chem., 35, 2792 (1996); (e) J.H. Kim, Chem. Lett., 156 (2000); (f) O. Iranzo, A.Y. Kovalevsky. J.R. Morrow and J.P. Richard, J. Am. Chem. Soc., 125, 1988 (2003); (g) O. Iranzo, T. Elmer, J.P. Richard and J.R. Morrow, Inorg. Chem., 42, 7737 (2003); (h) O. Iranzo, J.P. Richard and J.R. Morrow, Inorg. Chem., 43, 1743 (2004); (i) F.H. Fry, A.J. Fischmann, M.J. Belousoff, L. Spiccia and J. Brügger, Inorg. Chem., 44, 941 (2005); (j) M.Y. Yang, O. Iranzo, J.P. Richard and J.R. Morrow, J. Am. Chem. Soc., 127, 1064 (2005)
(a) G.C. Silver and W.C. Trogler, J. Am. Chem. Soc., 117, 3983 (1995); (b) E.L. Hegg and J.N. Burstyn, Inorg. Chem., 35, 7474 (1996); (c) J.H. Him and S.H. Kim, Chem. Lett., 32, 490 (2003); (d) T. Hirohama, H. Arii and M. Chikira, J. Inorg. Biochem., 98, 1778 (2004); (e) P.T. Selvi, H. Stoechli-Evans and M. Palaniandavar, J. Inorg. Biochem., 99, 2110 (2005); (f) P.F. Shi, Q. Jiang, J. Lin, Y.M. Zhao, L.P. Lin and Z.J. Guo, J. Inorg. Biochem., 100, 939 (2006)
C. Bolm, D. Kadereit and M. Valacchi, Synlett, 687 (1997)
Q.X. Li Q.H. Luo Y.Z. Li C.Y. Duan Q.Y. Tu (2005) Inorg. Chim. Acta 358 504 Occurrence Handle10.1016/j.ica.2004.07.010 Occurrence Handle1:CAS:528:DC%2BD2MXhtVOiuw%3D%3D
W.B. Qi, Y.Z. Li, J. Ni and Z.L. Wang, Acta Cryst., C59 (2003)
J. Robb R.D. Peacock (1986) Inorg. Chim. Acta 121 L15 Occurrence Handle10.1016/S0020-1693(00)87728-2 Occurrence Handle1:CAS:528:DyaL2sXpsVyrsw%3D%3D
A.A. Belal, L.J. Farrugia, R.D. Peacock and J. Robb, J. Chem. Soc., Dalton Trans., 931 (1989)
SAINT, Program for Data Extraction and Reduction, version 6.01; Siemens Analytical X-ray Instruments, Inc., Madison, WI
G.M. Sheldrick, SHELXTL Program for Refinement of Crystal Structures, version 6.01; Siemens Analytical X-ray Instruments, Inc., Madison, WI
W. Han L. Li W. Gu Z.Q. Liu S.P. Yan D.Z. Liao Z.H. Jiang P. Cheng (2004) J. Coord. Chem. 57 41 Occurrence Handle10.1080/00958970310001650078 Occurrence Handle1:CAS:528:DC%2BD2cXjt1aiurk%3D
I. Fallis L.J. Farrugia N.M. Macdonald R.D. Peacock (1993) Inorg. Chem. 32 779 Occurrence Handle10.1021/ic00058a002 Occurrence Handle1:CAS:528:DyaK3sXhtlyls7w%3D
A.A. Belal, L.J. Farrugia, R.D. Peacock and J. Robb, J. Chem. Soc., Dalton Trans., 931 (1989)
O. Schlager K. Wieghardt H. Grondey A. Rufinska B. Nuber (1995) Inorg. Chem. 34 6440 Occurrence Handle10.1021/ic00130a008 Occurrence Handle1:CAS:528:DyaK2MXps1GjtL0%3D
K. Weighardt U. Bossek P. Chaudhuri W. Herrmann (1982) Inorg. Chem. 21 4308 Occurrence Handle10.1021/ic00142a037
T. Weyhermüller, K. Weighardt and P. Chaudhuri, J. Chem. Soc., Dalton Trans, 3805 (1998)
I.A. Fallis, L.J. Farrugia, N.M. Macdonald and R.D. Peacock, J. Chem. Soc., Dalton Trans., 2759 (1993)
A. Diebold A. Elbouadili K.S. Hagen (2000) Inorg. Chem. 39 3915 Occurrence Handle10.1021/ic000456h Occurrence Handle1:CAS:528:DC%2BD3cXltlaht7Y%3D
S. Srinivasan J. Annaraj P.R. Athappan (2005) J. Inorg. Biochem. 99 876 Occurrence Handle10.1016/j.jinorgbio.2005.01.002 Occurrence Handle1:CAS:528:DC%2BD2MXhtlCkur8%3D
M. Qian S.H. Gou Z. Yu H.X. Ju Y. Xu C.Y. Duan X.Z. You (2001) Inorg. Chim. Acta 317 157 Occurrence Handle10.1016/S0020-1693(01)00326-7 Occurrence Handle1:CAS:528:DC%2BD3MXjslaltLc%3D
A.A. Belal, I. Fallis, L.J. Farrugia, N.M. Macdonald and R.D. Peacock, Chem. Commun., 402 (1991)
A. Haimov H. Cohen R. Neumann (2004) J. Am. Chem. Soc. 126 11762 Occurrence Handle10.1021/ja046349u Occurrence Handle1:CAS:528:DC%2BD2cXntF2hsrw%3D
J.E. Barker T. Ren (2005) Tetrahedron Lett. 46 6805 Occurrence Handle10.1016/j.tetlet.2005.08.033 Occurrence Handle1:CAS:528:DC%2BD2MXpsFyktL4%3D
B.C. Gilbert J.R.L. Smith A.M. i Payeras J. Oakes R.P. i Prats (2004) J. Mol. Catal. A: Chem. 219 265 Occurrence Handle10.1016/j.molcata.2004.05.012 Occurrence Handle1:CAS:528:DC%2BD2cXmtVSrurk%3D
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Feng, XM., Zhang, Z., Li, YZ. et al. Complexes of N,N′,N′′-tris(2-hydroxypropyl)-1,4,7-triazacyclononane (L): Structures of [CuL](ClO4)(NO3), [CoL](ClO4)2, [ZnL](ClO4)2 and the catalytic activity of [MnL](ClO4)2 towards olefin epoxidation with hydrogen peroxide. Transition Met Chem 32, 95–101 (2007). https://doi.org/10.1007/s11243-006-0137-7
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11243-006-0137-7