Research of Metalloporphyrins as Mimic Enzyme Catalysts

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1 PROGRESS IN CHEMISTRY Vol. 17 No. 4 Jul., ( ) ( ), : O627 ; O : A : X(2005) Research of Metalloporphyrins as Mimic Enzyme Catalysts Wang Lanzhi She Yuanbin 3 Xu Weiwei Zhang Yanhui ( Institute of Green Chemistry, Beijing University of Technology, Beijing , China) Ji Hongbing (School of Chemical and Energy Engineering, South China University of Technology, Guangzhou , China) Abstract The applications and mechanism of metalloporphyrins in catalytic oxidation are discussed. Quantum calculation method used in molecular design, uncovering relation between structure and catalytic activity of metalloporphyrins is reviewed. Recent works of authorsresearch group are also introduced. The future application of metalloporphyrins in catalysis is prospected. Key words metalloporphyrins ; oxidation reaction ; catalysts ; quantum calculation 18 P2450 ; Rothemund [1 ],, h ( TPP),2004,, : , : e2mail : edu. cn

2 4 679 Alder [2 ] ( : (1) ), min ( ) 10 % 30 %, ; (3) ;, 70 (4) 50 %, Lindsey [3 ] C H CH 2 Cl 2 BF 3 2, C H, TPPH 2 ; 30 % 40 %, 1L, :, 10 % 30 %,, ( ) [ ] DMF AlCl 3 N 2, TPPH 2 30 % [5,6 ] meso 2[ 42( N, N2 ) ] ( TDMAPPH 2 ) 2[ 42( N, N, H2 ) ] (TDMAPPSH 2 ), ( M2 TDMAPPTPS,M = Co,Cu,Zn,Mg,Mn,Ni) [7,8] 11, Alder Lindsey TXPPH 2 25 % 35 % 3 > > 90 % ; P2450 P2450 Eills [12 ] Labinger [13 ] P2450 [8 ],, 90 %, Fe Π [9,10 ] ; (2) ( ), ( P2450) (1) Eills [11 ] 1990 [ ]

3 680 17, 8, 2 ( ) ( ), FAB2MS UV2visible IR 2003 Tagliatesta [19 ] 2,62 Fe (TDCPP), MnTPPCl CoTPP, (2),,, oπp2no 2 oπp2clπ2hoπp2och 3 oπp2oh Mn 2 + Fe 2 + Co 2 + Cu 2 + Zn 2 +, 2 R C (O) O, (2a) (2b) (2c) [20 26 CO O 2 NO ] [15, ] Traylor [16 ] 4 8 (2,62 ) Murahashi [17 ] 70, : : NO 2 > Cl > H > OCH 3 > OH :Mn 2 + > Fe 2 + > Co 2 + : [27 ] 2004 [18 ],T( o2cl) PPFe, 2114 % :

4 4 681 [ ] (4a) (4b) [ TPPFe ] 2 O [ TPPMn ] 2 O [28 ] : 70, :, C H 21, Colleman [39 ] ( endo2cis) (face to face) 5 6, 41 O O, Jack [29 ], [ ], Haber [31 ] Maillard [40 ], F - Cl - Br - I - OH - CH 3 COO - [41 (5) : ] F - > CH 3 COO - > Cl - OH - > Br - > I - 31 P2450 (7) 51, : [32 37 ] 2, ; () PhIO ;

5 682 17, Fig. 1 The hypothetical catalytic cycle for an alkane to an alcohol using an iron porphyrin complex Fe O 2 Fe (1b) ; Fe O 2 Fe Geier [42 ] Fe O (1 PhIO c), Fe O ( RH) 70 %, Fe O 2 : Fe OH(1 d) ; Fe OH Fe O ( Fe ) 2 Fe 2O2Fe (1g) Machado [43 ] ( ) ( ), : 1 (1e) e (1f) Fe O Fe O ; Fe O (Fe ) 2 ( Fe O Fe ) ; Fe P2450 Fe [46 ], Groves [44 ],, PhIO NaClO H 2 O 2, Ellis [45 ] P2450 (1) : P2450 Fe O 2 (1 a) ;Fe O 2 2

6 4 683 [47 ] Fe ΠFe Fe, Fe Zakharieva [59 ] ( ) [48 52, ] 1999 Gygrgy [53 ] C H, L [60 ], ( TPPF 20 2 PM3 ZINDOΠ1 Lyons Fe ( ) O) 2002, Fujii [54 ] HOMO Gaussian03 HyperChem7. 0 [61,62 ] : (1) E HOMO E L2H (HOMO LUMO ), E HOMO E L2H, (2), ( ) E L2H, E L2H Fukui [55 ] (3) ESR (HOMO) (LUMO), ( ) + 2, Zwaans [56 ] ab initio 3 31 Melvin [57 ] AM1 PM3 9 ; LUMO HOMO H f, Yamamoto [58 ]

7 ((5) ), 2,,,, : (1) P2450 (2), (3) : ;, ; (4), ( ) [14] (He H S), (Huang J W),, [ 1 ] Rothemund P. J. Am. Chem. Soc., 1939, 61 (8) : [ 2 ] Adler A D, Longo F R, Finarelli J D, et al. J. Org. Chem., 1967, 32 : 476 [ 3 ] Lindsey J S, Schreiman I C, Hsu H C, et al. J. Org. Chem., 1987, 52 : [ 4 ] ( Guo C C), ( He X T), ( Zou G Y). (Chin. J. Org. Chem. ), 1991, 11 (4) : [ 5 ] (Pan J G), ( He M W), (Liu Q Q). (Chin. J. Org. Chem. ), 1993, 13 (5) : [ 6 ] ( Gao D), ( Zheng G D), ( Yang G M). (Chin. J. Org. Chem. ), 1994, 14 (3) : [ 7 ] (Shi T S), (Liu W), (Liu G F), (Wang X Q), ( Wang S Y). ( Chinese Journal of Applied Chemistry), 1998, 15 (3) : [ 8 ] (Liu W), (Shi T S), (An Q D), ( Yang D Z). ( Chemical Journal of Chinese Universities), 2001, 22 (1) : [ 9 ] Hayaishi O. Molecular Mechanism of Oxygen Activation, Chapter 1, 3, 10. New York : Academic Press, 1974 [10] (Wu Y), (Zhang D S). (Prog. Biochem. Biophys. ), 1983, (4) : 10 [11] Ellis P EJr, Lyons J E. Coord. Chem. Rev., 1990, 105 : [12] Ellis P E, Lyons J E. Catal. Lett., 1991, 8 : [13] Grinstaff M W, Hill M G, Labinger J, et al. Science, 1994, 264 : (Lao C L), (Ji L N). (Journal of Sun Yat2Sen University), 1997, 36 (3) : 6 11 [15] (He L C), (Deng R). (Journal of Instrumental Analysis), 2000, 19 (2) : 35 38

8 4 685 [16] Tralor P S, Dolphin D, Traylor T G. J. Chem. Soc., Chem. Comm., 1984, [17] Murahashi S, Naota T, Komiya K. Tetrahedron Lett., 1995, 36 (44) : [18] (Wang R M), (Wang Y P), (Lei Z Q). ( ) (Journal of Northwest Normal University, Natural Science), 2000, 36 : [19] Tagliatesta P, Pastorini A. J. Mol. Catal. A : Chem., 2003, 198 : [20] (Song X F), (Ji H B), ( Zhou X T), ( She Y B). ( Fine Chemicals), 2004, 21 (6) : [21] (Zhang Y H), (Song X F), ( Zhao G Y), (She YB), (Zhong R G). [43] Machado A M, Wypych F, Drechsel S M, Nakagaki S. Journal of (Chinese Science Abstracts), 2001, 7 (8) : [22] (She Y B), ( Zhang S F), ( Yang J Z). ( Journal of Beijing Technology University), 1999, 25 (1) : [23] ( She Y B), ( Yang J Z). ( Fine Chemicals), 1998, 15 (1) : [24] (She Y B), ( Zhang S F), ( Yang J Z). (Journal of Dalian University of Technology), 1999, 39 (1) : [25] (She Y B), ( Zhang S F), ( Yang J Z), ( Zhang Z X). (Journal of Beijing Technology University), 1998, 24 (1) : [26] (She Y B), ( Zhang S F), ( Yang J Z). (Dyestuffs Industry), 1998, 35 (5) : [27] Yuan Y, Ji H B, Chen Y X, Han Y, Song X F, She YB, Zhong R G. Org. Process. Res. Dev., 2004, 8 : [28] Fan L L, Wu S Z, She YB, Song X F, Bai J Q. The Proceedings of the 2nd International Conference on Functional Molecules. Dalian : Dalian University of Technology Press, [29] Linard J E, Ellis P E, Budge J R Jr, et al. J. Am. Chem. Soc., 1980, 102 : [30] (Chen J G), (Li Z X). ( ) (Journal of Xiamen University, Natural Science),1994, 33 (6) : [31] Haber J, Matachowski L, Pamin K, Poltowicz J. J. Mol. Catal., 2000, 162 : [32] ( Guo C C), (Zhu S J), ( Gui M D). (Acta Chimica Sinica), 1992, 50 : 129 [33] ( Guo C C), (Liu L Y). 401 : (Chemical Journal of Chinese Universities), 1993, 14 ( 8 ) : [34] ( Guo C C). (Acta Chimica Sinica), 1994, 52 : [35] ( Guo C C), (Lei Y W), (Zhang S). (Journal of Inorganic Chemistry), 1993, 9 ( 1) : [36] ( Guo C C), (Ding L Z), (Liang B X), ( Chen X B). ( Chemical [62] (Zhang Y H), (Zhong R G), (Zhou X Journal of Chinese University). 1996, 17 (4) : [37] ( Guo C C), ( Hao X D), ( Zhang X B), (Liang B X), (Chen X B). ( Chemical Journal of Chinese Universities), 1997, 18 (6) : [38] Guo C C, Peng Q J, Liu Q, Jiang G F. J. Mol. Catal. A : Chem., 2003, 192 : [39] Collman J P, Elliott C M, Halbert T R, Tovrog B S. Proc. Natl. Acad. Sci. USA, 1977, 74 : [40] Maillard P, Guerquin2Kem J L, Momenteau M. Tetrahedron Lett., 1991, 32 : [41] ( Guo C C), ( Zhang X B), ( Song J X), (Li H P). (Acta Chimica Sinica), 2000, 58 (3) : [42] Geier R G, Sasaki T. Tetrahedron, 1999, 55 : Colloid and Interface Science, 2002, 254 : [44] Groves J T, Nemo T E, Myers R S. J. Am. Chem. Soc., 1979, 101 (4) : [45] Lyons J E, Ellis P E, Mayers H K. J. Catal., 1995, 155 : [46] Groves J T, Kruper W J, Nemo T E, et al. J. Mol. Catal., 1980, (7) : [47] Showalter M C, Nenoff T M, Shelnutt J. Sandia Report Sand , 1996 [48] Guo C C, Peng Q J, et al. Appl. Catal. A : General, 2002, 230 : [49] Tagliatesta P, Pastorini A. J. Mol. Catal. A : Chem., 2003, 198 : [50] Zakharieva O, Trautwein A X, Veeger C. Biophys. Chem., 2000, 88 : [51] Traylor T G, Xu F, J. Am. Chem. Soc., 1987, 109 : [52] Davydov R, Makris T M, Kofman V, et al. J. Am. Chem. Soc., 2001, 123 : [53] KeserG M, Balogh G T, Bokotey S, et al. Tetrahedron, 1999, 55 : [54] Fujii H. Coord. Chem. Rev., 2002, 226 : [55] (Wang G X). (Atom Orbit and Molecule Orbit). (Beijing) : ( Higher Edu. Press), [56] Zwaans R, van Lenthe J H, den Boer D H W. J. Mol. Struct. (Theochem. ), 1995, 339 : [57] Zandle M E, Souza F D. J. Mol. Struct. ( Theochem. ), 1997, [58] Yamamoto S, Diercksen G H F, Karelson M. Chem. Phys. Lett., 2000, 318 : [59] Zakharieva O, Trautwein A X, Veeger C. Biophys. Chem., 2000, 88 : [60] LQ, Yu R, Shen G. J. Mol. Catal. A : Chem., 2003, 198 : 9 22 [61] She Y B, Zhou X T, Song X F, Bai J Q. Sixth International Symposium on Green Chemistry, Chengdu, T), (Ji H B), (She Y B). (Acta Chimica Sinica), 2004, 62 (22) :