suppmat51. 129KB Jun 05 2011 09:30:53 PM
Supporting information
Ligand structures of optimized zirconocene dichlorides.
1 2 3 4 5 6
Si
Si O
Si Si
7 8 9 10 11 12 13 14 15 16
Si O Si
Si Si
17 18 19 20 21 22 23 24 25 26
Si
Si N
N
Si
27 28 29 30 31 32 33 34 35 36 37
Si Si Si Si
38 39 40 41 42 43 44 45 46 47
Si
Si
48 49 50 51 52 53 54 55 56 57
58 59 60 61 62
O Si O Si O Si O Si O Si
O Si O Si
O
Si Si O
O Si O Si
O Si Si Si Si Si Si O O Si Si Si N N Si Si Si O Si Si Si
(2)
° ° °
HF Exp. HF Exp. HF Exp. HF Exp. HF Exp.
1 2.491 2.415 2.257 2.239 97.9 98.7 125.8 126.5 64.2 63.7 1
2 2.481 2.414 2.271 2.242 96.9 94.3 125.8 125.7 60.5 57.8 2
3 2.500 2.431 2.255 2.229 96.7 96.3 124.9 125.1 59.8 57.7 2
4 2.481 2.411 2.270 2.254 99.0 99.3 126.6 125.9 60.0 61.0 3
5 2.501 2.438 2.247 2.229 96.8 98.1 124.7 125.2 58.3 58.3 4
6 2.487 2.432 2.267 2.246 98.8 97.9 126.8 126.3 60.3 59.5 5
7 2.484 2.435 2.257 2.197 101.6 98.0 123.7 125.4 61.7 60.1 6
8 2.483 2.434 2.246 2.210 101.6 102.5 116.7 118.3 73.2 71.5 7
9 2.497 2.436 2.237 2.208 100.1 97.2 123.9 123.9 61.3 59.7 8
10 2.470 2.431 2.281 2.241 98.8 98.8 125.6 127.8 63.3 61.8 9
11 2.495 2.436 2.264 2.233 97.1 94.8 130.3 128.8 51.4 53.5 9
12 2.493 2.433 2.255 2.221 100.4 99.7 120.6 122.5 75.0 72.9 10
13 2.493 2.431 2.272 2.248 99.8 98.9 131.0 130.9 51.3 52.2 11
14 2.498 2.439 2.247 2.215 98.1 96.7 124.4 125.8 61.4 60.3 12
15 2.473 2.420 2.286 2.238 99.8 99.0 127.2 128.0 61.9 60.2 13
16 2.499 2.436 2.250 2.212 97.8 98.6 124.4 125.3 59.4 60.3 14
17 2.498 2.435 2.257 2.201 100.1 98.7 132.1 130.8 49.7 51.1 15
(3)
Molecule Zr-Cl (Å) Zr-Cp’(Å) Cl-Zr-Cl (°) Cp’-Zr-Cp’(°) Cp’-Cp’(°) Ref.
HF Exp. HF Exp. HF Exp. HF Exp. HF Exp.
19 2.483 2.428 2.253 2.199 101.7 99.6 119.1 120.6 73.1 69.6 17
20 2.484 2.431 2.261 2.223 97.7 95.9 124.1 123.8 63.0 62.4 18
21 2.472 2.411 2.299 2.242 98.0 98.3 127.9 127.9 65.5 61.9 19
22 2.504 2.449 2.253 2.232 95.3 96.1 125.9 126.1 60.5 60.4 20
23 2.502 2.443 2.259 2.227 96.3 96.8 131.1 130.2 53.5 55.8 21
24 2.487 2.431 2.267 2.231 101.1 97.1 127.3 127.2 59.1 58.9 22
25 2.486 2.444 2.244 2.217 97.8 97.2 123.7 123.8 61.1 59.0 23
26 2.480 2.427 2.265 2.224 100.4 98.6 124.4 125.9 63.5 61.8 23
27 2.478 2.430 2.265 2.213 101.0 97.9 125.0 126.9 62.6 60.4 24
28 2.497 2.428 2.251 2.211 101.9 99.0 124.6 126.3 62.7 61.0 25
29 2.498 2.430 2.268 2.228 100.9 98.0 124.6 126.2 65.1 63.7 25
30 2.504 2.441 2.244 2.211 100.0 98.4 126.5 127.7 58.5 57.7 26
31 2.476 2.432 2.253 2.207 99.2 98.1 117.8 118.5 73.5 71.2 27
32 2.497 2.450 2.245 2.203 98.5 97.0 130.8 129.6 49.7 50.2 28
33 2.484 2.422 2.279 2.237 93.3 95.0 126.9 129.1 61.8 59.2 29
34 2.491 2.428 2.267 2.237 94.0 94.8 126.9 127.2 59.6 57.7 30
35 2.495 2.441 2.253 2.196 99.0 95.7 131.6 131.5 50.9 51.2 31
36 2.493 2.442 2.235 2.177 101.0 98.8 123.5 123.2 58.3 55.3 32
(4)
38 2.502 2.448 2.252 2.215 100.1 100.1 124.3 124.8 62.0 61.2 34
39 2.507 2.438 2.284 2.239 92.8 89.6 132.6 130.3 51.0 54.1 35
40 2.472 2.423 2.280 2.247 100.2 99.3 126.4 128.0 61.4 60.8 36
41 2.478 2.420 2.278 2.248 98.8 96.8 127.7 128.6 61.8 59.1 37
42 2.486 2.438 2.234 2.187 101.8 97.9 119.6 119.8 64.8 62.7 38
43 2.498 2.432 2.250 2.221 96.1 96.5 131.5 131.3 51.6 52.9 39
44 2.481 2.439 2.255 2.213 100.0 99.8 124.5 125.1 60.4 60.0 40
45 2.474 2.429 2.247 2.199 102.1 100.1 115.8 117.1 72.9 71.6 41
46 2.469 2.429 2.280 2.254 98.8 98.3 125.5 127.6 63.5 63.3 42
47 2.494 2.434 2.261 2.231 98.5 99.4 124.5 126.5 63.2 61.7 42
48 2.486 2.437 2.246 2.199 101.4 98.3 115.4 116.4 73.7 72.1 43
49 2.482 2.437 2.248 2.191 101.5 98.3 115.1 116.3 73.6 71.5 44
50 2.475 2.424 2.271 2.235 98.0 97.1 124.9 125.3 61.8 60.4 45
51 2.478 2.426 2.270 2.227 99.4 97.6 125.7 126.3 60.3 59.7 45
52 2.487 2.406 2.258 2.207 98.7 97.2 115.0 117.4 75.8 76.2 46
53 2.494 2.441 2.261 2.231 98.7 97.3 124.6 126.4 63.3 61.8 47
54 2.473 2.414 2.261 2.211 99.3 99.1 117.8 118.6 75.3 73.5 48
55 2.481 2.414 2.277 2.236 98.5 97.2 127.6 129.5 58.9 57.8 49
(5)
Molecule Zr-Cl (Å) Zr-Cp’(Å) Cl-Zr-Cl (°) Cp’-Zr-Cp’(°) Cp’-Cp’(°) Ref.
HF Exp. HF Exp. HF Exp. HF Exp. HF Exp.
57 2.476 2.420 2.271 2.215 98.3 96.2 117.8 118.5 76.5 73.2 49
58 2.505 2.440 2.270 2.229 99.0 98.6 133.4 132.8 52.0 53.6 50
59 2.502 2.428 2.271 2.233 97.2 97.6 125.0 126.7 64.0 62.6 51
60 2.479 2.432 2.240 2.191 103.4 100.2 114.9 116.6 72.7 71.4 52
61 2.492 2.452 2.238 2.187 101.1 97.5 123.8 125.0 58.4 57.4 53
(6)
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555, 127.
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12, 1931.
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(7)
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14, 177.
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1688.
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H.; Zeigler, R. Organometallics1996, 15, 5046.
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Rieger, B. Chem. Ber.1997, 130, 747.
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1991, 2207.
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69.
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(8)
Brintzinger, H. H. J. Organomet. Chem. , 520, 63.
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Chem.)1996, 15, 473.
33.Wiesenfeldt, H.; Reinmuth, A.; Barsties, E.; Evertz, K.; Brintzinger, H. H. J. Organomet.
Chem.1989, 369, 359.
34.Gutmann, S.; Burger, P.; Hund, H. U.; Hofmann, J.; Brintzinger, H. H. J. Organomet.
Chem.1989, 369, 343.
35.Changtao, Q.; Jianhua, G.; Changqing, Y.; Jie, S.; Peiju, Z. J. Chem. Soc., Dalton Trans.
1993, 3441.
36.Stehling, U.; Diebold, J.; Kirsten, R.; Roll, W.; Brintzinger, H. H.; Jungling, S.; Mülhaupt,
R.; Langhauser, F. L. Organometallics1994, 13, 964.
37.Spaleck, W.; Kuber, F.; Winter, A.; Rohrmann, J.; Bachmann, B.; Antberg, M.; Dolle, V.;
Paulus, E. P. Organometallics1994, 13, 954.
38.Hafner, K.; Mink, C.; Lindner, H. J. Angew. Chem., Int. Ed. Engl.1994, 33, 1479.
39.Huttenloch, M. E.; Diebold, J.; Rief, U.; Brintzinger, H. H.; Gilbert, A. M.; Katz, T. J.
Organometallics1992, 11, 3600.
40.Rieger, B.; Jany, G.; Fawzi, R.; Steimann, M. Organometallics1994, 13, 647.
41.Green, M. L. H.; Ishihara, N. J. Chem. Soc., Dalton Trans.1994, 657.
42.Luttikhedde, H. J. G.; Leino, R. P.; Näsman, J. H.; Ahlgren, M.J.; Pakkanen, T. A. J.
(9)
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Piccolrovazzi, N. Organometallics1995, 14, 1256.
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(1)
Molecule Zr-Cl (Å) Zr-Cp’(Å) Cl-Zr-Cl (°) Cp’-Zr-Cp’(°) Cp’-Cp’(°) Ref.
HF Exp. HF Exp. HF Exp. HF Exp. HF Exp.
38 2.502 2.448 2.252 2.215 100.1 100.1 124.3 124.8 62.0 61.2 34
39 2.507 2.438 2.284 2.239 92.8 89.6 132.6 130.3 51.0 54.1 35
40 2.472 2.423 2.280 2.247 100.2 99.3 126.4 128.0 61.4 60.8 36
41 2.478 2.420 2.278 2.248 98.8 96.8 127.7 128.6 61.8 59.1 37
42 2.486 2.438 2.234 2.187 101.8 97.9 119.6 119.8 64.8 62.7 38
43 2.498 2.432 2.250 2.221 96.1 96.5 131.5 131.3 51.6 52.9 39
44 2.481 2.439 2.255 2.213 100.0 99.8 124.5 125.1 60.4 60.0 40
45 2.474 2.429 2.247 2.199 102.1 100.1 115.8 117.1 72.9 71.6 41
46 2.469 2.429 2.280 2.254 98.8 98.3 125.5 127.6 63.5 63.3 42
47 2.494 2.434 2.261 2.231 98.5 99.4 124.5 126.5 63.2 61.7 42
48 2.486 2.437 2.246 2.199 101.4 98.3 115.4 116.4 73.7 72.1 43
49 2.482 2.437 2.248 2.191 101.5 98.3 115.1 116.3 73.6 71.5 44
50 2.475 2.424 2.271 2.235 98.0 97.1 124.9 125.3 61.8 60.4 45
51 2.478 2.426 2.270 2.227 99.4 97.6 125.7 126.3 60.3 59.7 45
52 2.487 2.406 2.258 2.207 98.7 97.2 115.0 117.4 75.8 76.2 46
53 2.494 2.441 2.261 2.231 98.7 97.3 124.6 126.4 63.3 61.8 47
54 2.473 2.414 2.261 2.211 99.3 99.1 117.8 118.6 75.3 73.5 48
55 2.481 2.414 2.277 2.236 98.5 97.2 127.6 129.5 58.9 57.8 49
(2)
Molecule Zr-Cl (Å) Zr-Cp’(Å) Cl-Zr-Cl (°) Cp’-Zr-Cp’(°) Cp’-Cp’(°) Ref.
HF Exp. HF Exp. HF Exp. HF Exp. HF Exp.
57 2.476 2.420 2.271 2.215 98.3 96.2 117.8 118.5 76.5 73.2 49
58 2.505 2.440 2.270 2.229 99.0 98.6 133.4 132.8 52.0 53.6 50
59 2.502 2.428 2.271 2.233 97.2 97.6 125.0 126.7 64.0 62.6 51
60 2.479 2.432 2.240 2.191 103.4 100.2 114.9 116.6 72.7 71.4 52
61 2.492 2.452 2.238 2.187 101.1 97.5 123.8 125.0 58.4 57.4 53
(3)
References
1. Leino, R.; Luttikhedde, H. J. G.; Lehtonen, A.; Ekholm, P.; Näsman, J. H. J. Organomet. Chem. 1998, 558, 181.
2. Luttikhedde, H. J. G.; Leino, R.; Lehtonen, A.; Näsman, J. H. J. Organomet. Chem. 1998,
555, 127.
3. Leino, R.; Luttikhedde, H.; Wilén, C-E.; Sillanpää, R.; Näsman, J. H. Organometallics
1996, 15, 2450.
4. Leino, R.; Luttikhedde, H. J. G.; Lehmus, P.; Wilén, C-E.; Sjöholm, R.; Lehtonen, A.; Seppälä, J. V.; Näsman, J. H. Macromolecules 1997, 30, 3477.
5. Leino, R.; Luttikhedde, H. J. G.; Lehmus, P.; Wilen, C. E.; Sjöholm, R.; Lehtonen, A.; Seppälä, J. V.; Näsman, J. H. J. Organomet. Chem. 1998, 559, 65.
6. Bajgur, C. S.; Tikkanen, W. R.; Petersen, J. L. Inorg. Chem. 1985, 24, 2539.
7. Llinas, G. H.; Day, R. O.; Rausch, M. D.; Chien, J. C. W. Organometallics 1993, 12,
1283.
8. Erker, G.; Wilker, S.; Kruger, C.; Goddard, R. J. Am. Chem. Soc. 1992, 114, 10983.
9. Herrmann, W. A.; Rohrmann, J.; Herdtweck, E.; Spaleck, W.; Winter, A. Angew. Chem. Int. Ed. Engl. 1989, 28, 1511.
10.Mengele, G.; Diebold, J.; Troll, C.; Roll. W.; Brintzinger, H. H. Organometallics 1993,
12, 1931.
11.Naderer, H.; Siebel, E.; Fischer, R. D. J. Organomet. Chem. 1996, 518, 181.
12.Rheingold, A. L.; Robinson, N. P.; Whelan, J.; Bosnich, B. Organometallics 1992, 11,
1869.
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(4)
14.Wild, F. R. W. P.; Wasiucionek, M.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem.
1985, 288, 63.
15.Ciruelos, S.; Cuenca, T.; Gomez-Sal, P.; Manzanero, A.; Royo, P. Organometallics 1995,
14, 177.
16.Razawi, A.; Atwood, J. L. J. Organomet. Chem. 1993, 459, 117.
17.Cano, A.; Cuenca, T.; Gomez-Sal, P.; Royo, B.; Royo, P. Organometallics 1994, 13,
1688.
18.Resconi, R.; Piemontesi, F.; Camurati, I.; Balboni, D.; Sironi, A.; Moret, M.; Rychlicki, H.; Zeigler, R. Organometallics 1996, 15, 5046.
19.Jany, G.; Repo, T.; Gustafsson, R.; Leskelä, M.; Polamo, M.; Klinga, M.; Dietrich, U.; Rieger, B. Chem. Ber. 1997, 130, 747.
20.Jany, G.; Fawzi, R.; Steimann, M.; Rieger, B. Organometallics 1997, 16, 544.
21.Huttenloch, M. E.; Dorer, B.; Rief, U.; Prosenc, M.-H.; Schmidt, K.; Brintzinger, H. H. J. Organomet. Chem. 1997, 541, 219.
22.Bandy, J. A.; Green, M. L. H.; Gardiner, I. M.; Prout, K. J. Chem. Soc. , Dalton Trans.
1991, 2207.
23.Burger, P.; Hortmann, K.; Diebold, J.; Brintzinger, H. H. J. Organomet. Chem. 1991, 417,
9.
24.Gauthier, W. J.; Corrigan, J. F.; Taylor, N. J.; Collins, S. Macromolecules 1995, 28, 3771.
25.Mansel, S.; Rief, U.; Prosenc, M. H.; Kirsten, R.; Brintzinger, H. H. J. Organomet. Chem.
1996, 512, 225.
26.Wochner, F.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1985, 288,
69.
27.Alt, H. G.; Zenk, R.; Milius, W. J. Organomet. Chem. 1996, 514, 257.
(5)
29.Barsties, E.; Schaible, S.; Prosenc. M. H.; Rief, U.; Roll, W.; Weyand, O.; Dorer, B.; Brintzinger, H. H. J. Organomet. Chem. 1996, 520, 63.
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31.Thiele, K. T.; Schliessburg, Ch.; Baumeister, K.; Hassler, K. Z. Anorg. Allg. Chem. 1996,
622, 1806.
32.Wang, J-X.; Zhang, L-C.; Yang, D-Y.; He, Z-J.; Chen, S-S. Jiegou Huaxue (J. Struct. Chem.) 1996, 15, 473.
33.Wiesenfeldt, H.; Reinmuth, A.; Barsties, E.; Evertz, K.; Brintzinger, H. H. J. Organomet. Chem. 1989, 369, 359.
34.Gutmann, S.; Burger, P.; Hund, H. U.; Hofmann, J.; Brintzinger, H. H. J. Organomet. Chem. 1989, 369, 343.
35.Changtao, Q.; Jianhua, G.; Changqing, Y.; Jie, S.; Peiju, Z. J. Chem. Soc., Dalton Trans.
1993, 3441.
36.Stehling, U.; Diebold, J.; Kirsten, R.; Roll, W.; Brintzinger, H. H.; Jungling, S.; Mülhaupt, R.; Langhauser, F. L. Organometallics 1994, 13, 964.
37.Spaleck, W.; Kuber, F.; Winter, A.; Rohrmann, J.; Bachmann, B.; Antberg, M.; Dolle, V.; Paulus, E. P. Organometallics 1994, 13, 954.
38.Hafner, K.; Mink, C.; Lindner, H. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1479.
39.Huttenloch, M. E.; Diebold, J.; Rief, U.; Brintzinger, H. H.; Gilbert, A. M.; Katz, T. J. Organometallics 1992, 11, 3600.
40.Rieger, B.; Jany, G.; Fawzi, R.; Steimann, M. Organometallics 1994, 13, 647.
41.Green, M. L. H.; Ishihara, N. J. Chem. Soc., Dalton Trans. 1994, 657.
42.Luttikhedde, H. J. G.; Leino, R. P.; Näsman, J. H.; Ahlgren, M.J.; Pakkanen, T. A. J. Organomet. Chem. 1995, 486, 193.
(6)
43.Erker, G.; Psiorz,C.; Frohlich, R. Z. Naturforsch., Teil B 1995, 50, 469.
44.Erker, G.; Psiorz,C.; Frohlich, R.; Grehl, M.; Kruger, C.; Noe, R.; Nolte, M. Tetrahedron
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