Quantum chemical study of the mechanism of ethylene elimination in silylative coupling of olefins

Journal of Molecular Modeling

Volumn 13, Issue 4, 2007, Pages 477-483

  Hoffmann, Marcin ^a,b   Marciniec, Bogdan ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b BIOINFOBANK INSTITUTE   (Poland)

Author keywords

Density functional calculations; Reaction mechanisms; Silylation; Silylative coupling of olefins

Indexed keywords

ALKENE DERIVATIVE; CARBON; ETHYLENE; HYDROGEN; RUTHENIUM; SILICONE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODEL; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELIMINATION REACTION; PRIORITY JOURNAL; QUANTUM CHEMISTRY; SILYLATION;

ALKENES; CARBON; CATALYSIS; ETHYLENES; MODELS, CHEMICAL; MOLECULAR CONFORMATION; RUTHENIUM; SILANES; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

EID: 33947166903     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-006-0166-3     Document Type: Article

References (63)

1. Wakatsuki Y, Yamazaki H, Nakano M, Yamamoto Y (1991) J Chem Soc Chem Commun 703-704
2. Marciniec B, Pietraszuk C (1995) J Chem Soc Chem Commun 2003-2004
3. Marciniec B, Pietraszuk C (1997) Organometallics 16:4320-4326
4. Marciniec B, Pietraszuk C (2003) Curr Org Chem 7:691-735
5. Marciniec B, Pietraszuk C (2004) Topics in Organometallic Chemistry vol. 11 (P.Dixneuf ed,). Springer Verlag, Berlin, pp 197-248
6. Marciniec B (2005) Coord Chem Revs 249:2374-2390
7. Abbasoglu R, Yilmaz SS (2006) J Mol Model 12:290-296
8. Sikorska E, Khmelinskii I, Kubicki M, Prukala W, Hoffmann M, Machado IF, Ferreira LFV, Karolczak J, Worrall DR, Krawczyk A, Insinska-Rak M, Sikorski M (2006) J Phys Chem A 110:4638-4648
9. Zhang JG, Li QL, Zhang SW (2006) J Mol Model 12:190-196
10. Li QS; Zhang Y, Zhang S (2005) J Mol Model 11:41-47
11. Sharma K, Kubli-Garfias C (2005) J Mol Model 11:135-140
12. Goldfuss B, Schumacher M (2006) J Mol Model 12:591-595
13. Mitoraj M, Michalak A (2005) J Mol Model 11:341-350
14. Hoffmann M, Khavrutskii IV, Musaev DG, Morokuma K (2004) Int J Quant Chem 99:972-980
15. Eitner K, Bartl F, Brzezinski B, Schroeder G (2001) Supramol Chem 13:627-635
16. Buhl M (2000) J Mol Model 6:112-118
17. Borve KJ, Jensen VR, Karlsen T, Stovneng JA, Swang O (1997) J Mol Model 3:193-202
18. Grabarkiewicz T, Hoffmann M (2006) J Mol Model 12:205-212
19. Plutecka A, Hoffmann M, Rychlewska U, Kucybala Z, Paczkowski J, Pyszka I (2006) Acta Crystallogr B 62:135-142
20. Ruangpornvisuti V, Wanno B (2004) J Mol Model 10: 418-426
21. von Grotthuss M, Wyrwicz LS, Pas J, Rychlewski L (2004) Science 304: 1597-1599
22. Hoffmann M, Plutecka A, Rychlewska U, Kucybala Z, Paczkowski J, Pyszka I (2005) J Phys Chem A 109:4568-4574
23. Schroeder G, Wysocka W, Leska W, Kolanos R, Eitner K, Przybylak JK (2002) J Mol Struct 616:193-199
24. Hoffmann M, Rychlewski J (2001) J Am Chem Soc 123:2308-2316
25. Pumera M, Rulisek L (2006) J Mol Model 12:799-803
26. Plewczynski D, Spieser SA, Koch UJ (2006) J Chem Inf Model 46:1098-1106
27. Patroniak V, Stefankiewicz AR, Lehn J-M, Kubicki M, Hoffmann M (2006) Eur. J Inorg Chem 144-149
28. Hoffmann M (2005) Pol J Chem 79: 1179-1185
29. Hoffmann M, Rychlewska U, Warzajtis B (2005) CrystEngComm 7:260-265
30. Pas J, von Grotthuss M, Wyrwicz LS, Rychlewski L, Barciszewski J (2004) FEBS Lett 576:287-290
31. Olejniczak M, Gdaniec Z, Fischer A, Grabarkiewicz T, Bielecki L, Adamiak RW (2002) Nucleic Acids Res 30:4241
32. Honorio KM, da Silva ABF (2005) J Mol Model 11:200-209
33. Pas J, Wyszko E, Rolle K, Rychlewski L, Nowak S, Zukiel R, Barciszewski J (2006) Int J Biochem Cell Biol 38:1594-1602
34. Hoffmann M, Chrzanowska M, Hermann T, Rychlewski J (2005) J Med Chem 48:4482-4486
35. Plewczynski D, Tkacz A, Wyrwicz LS, Rychlewski L (2005) Bioinformatics 21:2525-2527
36. Plewczynski D, Rychlewski L, Ye Y, Jaroszewski L, Godzik A (2004) BMC Bioinformatics 5:98
37. Hoffmann M, Rychlewski J, Chrzanowska M, Hermann T (2001) J Am Chem Soc 123:6404-6409
38. Antonczak S, Monard G, Ruiz-López M, Rivail JL (2000) J Mol Model 6:527-538
39. Suresh CH, Koga N (2004) Organometallics 23:76-80
40. Adlhart C, Chen P (2003) Helv Chim Acta 86:941-949
41. van Rensburg WJ, Steynberg PJ, Meyer WH, Kirk MM, Forman GS (2004) J Am Chem Soc 126:14332-14333
42. Adlhart C, Chen P (2004) J Am Chem Soc 126:3496-3510
43. Sakaki S, Mizoe N, Sugimoto M (1998) Organometallics 17:2510-2523
44. Sakaki S, Sumimoto M, Fukuhara M, Sugimoto M, Fujimoto H, Matsuzaki S (2002) Organometallics 21:3788-3802
45. Becke AD (1993) J Chem Phys 98:5648-5652
46. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785-789
47. Andrae D, Haeussermann U, Dolg M, Stoll H, Preuss H (1990) Theor Chim Acta 77:123-141
48. Bergner A, Dolg M, Kuechle W, Stoll H, Preuss H (1993) Mol Phys 80:1431-1441
49. Hay PJ, Wadt WR (1985) J Chem Phys 82:299-310
50. Wadt WR, Hay PJ (1985) J Chem Phys 82:284-298
51. Ditchfield R, Hehre WJ, Pople JA (1971) J Chem Phys 54:724-728
52. Hehre WJ, Ditchfield R, Pople JA (1972) J Chem Phys 56:2257-2261
53. Hariharan PC, Pople JA (1974) Mol Phys 27:209-214
54. Gordon MS (1980) Chem Phys Lett 76:163-168
55. Hariharan PC, Pople JA (1973) Theor Chim Acta 28:213-222
56. Clark T, Chandrasekhar J, Spitznagel GW, Schleyer PvR (1983) J Comp Chem 4:294-301
57. Frisch MJ, Pople JA, Binkley JS (1984) J Chem Phys 80:3265-3269
58. Gaussian 03, Revision B05, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T Jr, Kudin KN, Burant JC, Millam M, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin J, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels D, Strain MC, Farkas O, Malick DK, Rabuck D, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul G, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian Inc, Pittsburgh PA
59. van der Boom ME, Iron MA, Atasoylu O, Shimon LJW, Rozenberg H, Ben-David Y, Konstantinovski L, Martin JML, Milstein D (2004) Inorg Chim Acta 357:1854-1864
60. Iron MA, Lo HC, Martin JML, Keinan E (2002) J Am Chem Soc 124:7041-7054
61. Clot E, Eisenstein O (2004) Structure & Bonding vol. 113. In: Kaltsoyannis N, McGrady JE (eds) Principles and applications of density functional theory in inorganic chemistry II. Springer, Berlin Heidelberg, pp 1-36
62. Thakur TS, Desiraju GR (2006) Chem Commun 552-554
63. Cracknell RB, Orpen AG, Spencer JL (1984) J Chem Soc, Chem Commun 326-328