Reaction pathways for addition of H2 to amido-ditetrylynes R2N-EE-NR2 (E = Si, Ge, Sn). A theoretical study

Organometallics

Volumn 32, Issue 22, 2013, Pages 6666-6673

  Hermann, Markus ^a   Goedecke, Catharina ^a   Jones, Cameron ^b   Frenking, Gernot ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; DISPERSION INTERACTION; ENERGY CALCULATION; HYDROGENATION REACTIONS; QUANTUM CHEMICAL CALCULATIONS; REACTION PATHWAYS; STEPWISE REACTION; THEORETICAL STUDY;

ACTIVATION ENERGY; CHEMICAL COMPOUNDS; GERMANIUM; HYDROGENATION; QUANTUM CHEMISTRY; SILICON; SOLVENTS; TIN;

ADDITION REACTIONS;

EID: 84888597667     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om4007888     Document Type: Article

References (62)

1. Power, P. P. Acc. Chem. Res. 2011, 44, 627
2. Asay, M.; Jones, C.; Driess, M. Chem. Rev. 2011, 111, 354
3. Yao, S.; Xiong, Y.; Driess, M. Organometallics 2011, 30, 1748
4. Power, P. P. Nature 2010, 463, 171
5. Fischer, R. C.; Power, P. P. Chem. Rev. 2010, 110, 3877
6. Schnöckel, H. Chem. Rev. 2010, 110, 4125
7. Lee, V. Y.; Sekiguchi, A. Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb; Wiley: Chichester, U.K., 2010.
8. Pu, L.; Twamley, B.; Power, P. P. J. Am. Chem. Soc. 2000, 122, 3524
9. Phillips, A. D.; Wright, R. J.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 2002, 124, 5930
10. Stender, M.; Phillips, A. D.; Wright, R. J.; Power, P. P. Angew. Chem. 2002, 114, 1863
11. Sekiguchi, A.; Kinjo, R.; Ichinohe, M. Science 2004, 305, 1755
12. Disilylynes were previously synthesized but could not be characterized by X-ray analysis by: Wiberg, N.; Niedermeyer, Fischer, G.; Nöth, H.; Suter, M. Eur. J. Inorg. Chem. 2002, 1066
13. Wiberg, N.; Vasisht, S. K.; Fischer, G.; Mayer, P. Z. Anorg. Allg. Chem. 2004, 630, 1823
14. Bogey, M.; Bolvin, H.; Demuyneck, C.; Destombes, J.-L. Phys. Rev. Lett. 1991, 66, 413
15. Cordonnier, M.; Bogey, M.; Demuynck, C.; Destombes, J.-L. J. Chem. Phys. 1992, 97, 7984
16. Wang, X.; Andrews, L.; Kushto, G. J. Phys. Chem. A 2002, 106, 5809
17. Wang, X.; Andrews, L.; Chertihin, G. V.; Souer, P. F. J. Phys. Chem. A 2002, 106, 6302
18. Andrews, L.; Wang, X. J. Phys. Chem. A 2002, 106, 7697
19. Wang, X.; Andrews, L. J. Am. Chem. Soc. 2003, 125, 6581
20. Lischka, H.; Köhler, H. J. Am. Chem. Soc. 1983, 105, 6646
21. Binkley, J. S. J. Am. Chem. Soc. 1984, 106, 603
22. Kalcher, J.; Sax, A.; Olbrich, G. Int. J. Quantum Chem. 1984, 25, 543
23. Köhler, H.-J.; Lischka, H. Chem. Phys. Lett. 1984, 112, 33
24. Clabo, D. A.; Schaefer, H. F. J. Chem. Phys. 1986, 84, 1664
25. Thies, B. S.; Grev, R. S.; Schaefer, H. F. Chem. Phys. Lett. 1987, 140, 355
26. Koseki, S.; Gordon, M. S. J. Phys. Chem. 1988, 92, 364
27. Koseki, S.; Gordon, M. S. J. Phys. Chem. 1989, 93, 118
28. Colegrove, B. T.; Schaefer, H. F. J. Phys. Chem. 1990, 94, 5593
29. Grev, R. S.; De Leeuw, B. J.; Schaefer, H. F. Chem. Phys. Lett. 1990, 165, 257
30. Colegrove, B. T.; Schaefer, H. F. J. Am. Chem. Soc. 1991, 113, 1557
31. Grev, R. S. Adv. Organomet. Chem. 1991, 33, 125
32. Caputo, C. A.; Power, P. P. Organometallics 2013, 32, 2278
33. Sekiguchi, A. Pure Appl. Chem. 2008, 80, 447
34. Power, P. P. Organometallics 2007, 26, 4362
35. Rivard, E.; Power, P. P. Inorg. Chem. 2007, 46, 10047
36. Takagi, N.; Nagase, S. Organometallics 2007, 26, 3627
37. Lein, M.; Krapp, A.; Frenking, G. J. Am. Chem. Soc. 2005, 127, 6290
38. Bridgeman, A. J.; Ireland, L. R. Polyhedron 2001, 20, 2841
39. Chen, Y.; Hartmann, M.; Diedenhofen, M.; Frenking, G. Angew. Chem., Int. Ed. Engl. 2001, 40, 2052
40. Spikes, G. H.; Fettinger, J. C.; Power, P. P. J. Am. Chem. Soc. 2005, 127, 12232
41. Peng, Y.; Brynda, M.; Ellis, B. D.; Fettinger, J. C.; Rivard, E.; Power, P. P. Chem. Commun. 2008, 6041
42. Zhao, L. L.; Huang, F.; Lu, G.; Wang, Z.-X.; Schleyer, P.v.R. J. Am. Chem. Soc. 2012, 134, 8856
43. Li, J.; Schenk, C.; Goedecke, C.; Frenking, G.; Jones, C. J. Am. Chem. Soc. 2011, 133, 18622
44. Li, J.; Stasch, A.; Schenk, C.; Jones, C. Dalton Trans. 2011, 40, 10448
45. Hadlington, T. J.; Hermann, M.; Li, J.; Frenking, G.; Jones, C. Angew. Chem., Int. Ed. 2013, 52, 10199
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K, N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C.01; Gaussian, Inc., Wallingford, CT, 2009.
47. TURBOMOLE V6.4 2012, a development of the University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH, since 2007; available from www.turbomole.com.
48. Becke, A. D. Phys. Rev. A 1988, 38, 3098
49. Perdew, J. P. Phys. Rev. B 1986, 33, 8822
50. Weigend, F.; Häser, M.; Patzelt, H.; Ahlrichs, R. Chem. Phys. Lett. 1998, 294, 143
51. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297
52. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571
53. Metz, B.; Stoll, H.; Dolg, M. J. Chem. Phys. 2000, 113, 2563
54. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104
55. Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799
56. Mitoraj, M. P.; Michalak, A.; Ziegler, T. J. Chem. Theory Comput. 2009, 5, 962
57. Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 46, 1
58. Mitoraj, M. P.; Michalak, A. J. Mol. Model. 2007, 13, 347
59. Mitoraj, M. P.; Michalak, A.; Ziegler, T. Organometallics 2009, 28, 3727
60. Grimme, S.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 12639
61. Fukui, K. Acc. Chem. Res. 1971, 4, 57
62. Fukui, K. Theory of Orientation and Stereoselection; Springer Verlag: Berlin, 1975.