Dimerization mechanisms of heterocyclic carbenes

Journal of Physical Organic Chemistry

Volumn 18, Issue 4, 2005, Pages 298-309

  Graham, David C ^a   Cavell, Kingsley J ^b   Yates, Brian F ^a  

^a UNIVERSITY OF TASMANIA   (Australia)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

DFT calculations; Dimerization; Heterocyclic carbenes

Indexed keywords

ALCOHOLS; CATALYSIS; CHEMICAL ACTIVATION; DIMERIZATION; PROBABILITY DENSITY FUNCTION; PROTONS; REACTION KINETICS;

ACTIVATION BARRIERS; DFT CALCULATIONS; HETEROCYCLIC CARBENES; MOLECULAR ORBITAL CALCULATIONS;

FULLERENES;

EID: 15744367540     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.846     Document Type: Article

References (53)

1. Wanzlick H-W, Schikora E. Chem. Ber. 1961; 94: 2389-2393.
2. Arduengo AJ, Harlow RL, Kline M. J. Am. Chem. Soc. 1991; 113: 361-363.
3. Arduengo AJ, Goerlich JR, Marshall WJ. Liebigs Ann.-Recl. 1997; 365-374.
4. Alder RW, Butts CP, Orpen AG. J. Am. Chem. Soc. 1998; 120: 11526-11527.
5. Merceron N, Miqueu K, Baceiredo A, Bertrand G. J. Am. Chem. Soc. 2002; 124: 6806-6807.
6. Denk MK, Thadani A, Hatano K, Lough AJ. Angew. Chem. Int. Ed. Engl. 1997; 36: 2607-2609.
7. Cheng MJ, Hu CH. Chem. Phys. Lett. 2001; 349: 477-482.
8. Cheng MJ, Hu CH. Chem. Phys. Lett. 2000; 322: 83-90.
9. Heinemann C, Thiel W. Chem. Phys. Lett. 1994; 217: 11-16.
10. Su MD, Chu SY. Inorg. Chem. 1999; 38: 4819-4823.
11. Metzger J, Larive H, Dennilauler R, Baralle R, Gaurat C. Bull. Soc. Chim. Fr. 1964; 2857-2867.
12. Castells J, LopezCalahorra F, Geijo F, Perez-Dolz R, Bassedas M. J. Heterocycl. Chem. 1986; 23: 715-720.
13. Chen YT, Barletta GL, Haghjoo K, Cheng JT, Jordan F. J. Org. Chem. 1994; 59: 7714-7722.
14. Bordwell FG, Satish AV. J. Am. Chem. Soc. 1991; 113: 985-990.
15. Castells J, Domingo L, Lopezcalahorra F, Marti J. Tetrahedron Lett. 1993; 34: 517-520.
16. Chen YT, Jordan F. J. Org. Chem. 1991; 56: 5029-5038.
17. LopezCalahorra F, Castro E, Ochoa A, Marti J. Tetrahedron Lett. 1996; 37: 5019-5022.
18. Denk MK, Thadani A, Hatano K, Lough AJ. Angew. Chem. Int. Ed. Engl. 1997; 36: 2607-2609, footnote 19.
19. Hahn FE, Wittenbecher L, Le Van D, Frohlich R. Angew. Chem. Int. Ed. Engl. 2000; 39: 541-544.
20. Taton TA, Chen P. Angew. Chem. Int. Ed. Engl. 1996; 35:1011-1013.
21. Alder RW, Blake ME, Oliva JM. J. Phys. Chem. A 1999; 103: 11200-11211.
22. Oliva JM. Chem. Phys. Lett. 1999; 302: 35-42.
23. Nyulászi L, Veszpremi T, Forro A. Phys. Chem. Chem. Phys. 2000; 2: 3127-3129.
24. Carter EA, Goddard WA III. J. Phys. Chem. 1986; 90: 998-1001.
25. Hammond GS. J. Am. Chem. Soc. 1955; 77: 334-338.
26. Becke AD. J. Chem. Phys. 1993; 98: 5648-5652.
27. Becke AD. Phys. Rev. A. 1988; 38: 3098-3100.
28. Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785-789.
29. Hariharan PC, Pople JA. Theor. Chim. Acta 1973; 28: 213-222.
30. Krishnan R, Binkley JS, Seeger R, Pople JA. J. Chem. Phys. 1980; 72: 650-654.
31. McLean AD, Chandler GS. J. Chem. Phys. 1980; 72: 5639-5648.
32. Frisch MJ, Pople JA, Binkley JS. J. Chem. Phys. 1984; 80: 3265-3269.
33. Cizek J. Adv. Chem. Phys. 1969; 14: 35-89.
34. Purvis GD, Bartlett RJ. J. Chem. Phys. 1982; 76: 1910-1918.
35. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challa-combe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.7. Gaussian: Pittsburgh, PA, 1998.
36. Geijo F, LopezCalahorra F, Olivella S. J. Heterocycl. Chem. 1984; 21: 1785-1788.
37. Sauers RR. Tetrahedron Lett. 1996; 37: 149-152.
38. Kuhn N, Kratz T. Synthesis 1993; 561-562.
39. Schwerdtfeger P, Laakkonen L, Pyykko P. J. Chem. Phys. 1992; 96: 6807-6819.
40. Hoffmann R, Gleiter R, Mallory FB. J. Am. Chem. Soc. 1970; 92: 1460-1466.
41. Arduengo AJ III, Dias HVR, Calabrese JC, Davidson F. Inorg. Chem. 1993; 32: 1541-1542.
42. Cooper WF, Edmonds JW, Wudl F, Coppens P. Cryst. Struct. Commun. 1974; 3: 23.
43. Cetinkaya E, Hitchcock PB, Kucukbay H, Lappert MF, Aljuaid S. J. Organomet. Chem. 1994; 481: 89-95.
44. Cetinkaya E, Hitchcock PB, Jasim HA, Lappert MF, Spyropoulos K. J. Chem. Soc., Perkin Trans. 1 1992; 561-567.
45. Anderson DM, Hitchcock PB, Lappert MF. J. Organomet. Chem. 1989; 363: C7-C11.
46. Bourissou D, Guerret O, Gabbai FP, Bertrand G. Chem. Rev. 2000; 100: 39-91.
47. Fekete A, Nyulaszi L. J. Organomet. Chem. 2002; 643-644: 278-284.
48. Arduengo AJ, Dias HVR, Dixon DA, Harlow RL, Klooster WT, Koetzle TF. J. Am. Chem. Soc. 1994; 116: 6812-6822.
49. Jursic BS. J. Chem. Soc., Perkin Trans. 2 1999; 1805-1809.
50. Arduengo AJ, Calabrese JC, Davidson F, Dias HVR, Goerlich JR, Krafczyk R, Marshall WJ, Tamm M, Schmutzler R. Helv. Chim. Acta 1999; 82: 2348-2364.
51. Herrmann WA, Kocher C. Angew. Chem. Int. Ed. Engl. 1997; 36: 2163-2187.
52. Arduengo AJ, Gamper SF, Tamm M, Calabrese JC, Davidson F, Craig HA. J. Am. Chem. Soc. 1995; 117: 572-573.
53. Magill AM, Cavell KJ, Yates BF. J. Am. Chem. Soc. 2004; 126(28): 8717-8724.