Triplet 1,3-diphenylpropynylidene (Ph-C-C-C-Ph)

Journal of the American Chemical Society

Volumn 129, Issue 8, 2007, Pages 2308-2315

  DePinto, Jeffrey T ^a   DeProphetis, Wendy A ^a   Menke, Jessica L ^a   McMahon, Robert J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE TRAPPING; CONFORMATIONAL ISOMERS; EQUILIBRIUM STRUCTURE; NON-RELAXED CONFORMER;

CONFORMATIONS; INFRARED SPECTROSCOPY; MOLECULAR STRUCTURE; PARAMAGNETIC RESONANCE; PHOTOCHEMICAL REACTIONS; PHOTOLYSIS;

AROMATIC HYDROCARBONS;

1,3 DIPHENYLDIAZOPROPYNE; 1,3 DIPHENYLPROPYNYLIDENE; ACETYLENE DERIVATIVE; CARBENOID; CARBONYL OXIDE; DIOXIRANE; DIPHENYL 1,2 PROPADIENYLIDENE; DIPHENYLALKYLAMINE; DIPHENYLCYCLOPROPENYLIDENE; ETHYLENE OXIDE DERIVATIVE; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CONFORMATION; DENSITY FUNCTIONAL THEORY; GEOMETRY; LOW TEMPERATURE; PHOTOLYSIS; ULTRAVIOLET SPECTROSCOPY;

EID: 33847637524     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066300j     Document Type: Article

References (62)

1. Kaiser, R. I.; Ochsenfeld, C.; Stranges, D.; Head-Gordon, M.; Lee, Y. T. Faraday Discuss. 1998, 183-204.
2. Smith, I. W. M.; Herbst, E.; Chang, Q. Mon. Not. R. Astron. Soc. 2004, 250, 323-330.
3. Cool, T. A.; McIlroy, A.; Qi, F.; Westmoreland, P. R.; Poisson, L.; Peterka, D. S.; Ahmed, M. Rev. Sci. Instrum. 2005, 76, 094102.
4. Miller, J. A.; Klippenstein, S. J. J. Phys. Chem. A 2003, 107, 2680-2692.
5. Padwa, A.; Austin, D. J.; Gareau, Y.; Kassir, J. M.; Xu, S. L. J. Am. Chem. Soc. 1993, 115, 2637-2647.
6. Hansen, E. C.; Lee, D. Acc. Chem. Res. 2006, 39, 509-519.
7. Sixl, H. In Advances in Polymer Science; Cantow, H.-J., Ed.; New York, 1984; Vol. 63, pp 49-90.
8. Bloor, D.; Chance, R. R. Polydiacetylenes: Synthesis, Structure, and Electronic Properties; Martinus Nihhoff: Dordrecht, 1985; Vol. 102.
9. Edelmann, M. J.; Odermatt, S.; Diederich, F. Chimia 2001, 55, 132-138.
10. Ikoma, T.; Okada, S.; Nakanishi, H.; Akiyama, K.; Tero-Kubota, S. Phys. Rev. B: Condens. Matter 2002, 66, 014423.
11. Akai-Kasaya, M.; Shimizu, K.; Watanabe, Y.; Saito, A.; Aono, M.; Kuwahara, Y. Phys. Rev. Lett. 2003, 91, 255501.
12. Carpick, R. W.; Sasaki, D. Y.; Marcus, M. S.; Eriksson, M. A.; Burns, A. R. J. Phys.: Condens. Matter 2004, 16, R679-R697.
13. Skell, P. S.; Klebe, J. J. Am. Chem. Soc. 1960, 82, 247-248.
14. Bernheim, R. A.; Kempf, R. J.; Gramas, J. V.; Skell, P. S. J. Chem. Phys. 1965, 43, 196-200.
15. Bernheim, R. A.; Kempf, R. J.; Reichenbecher, E. F. J. Magn. Reson. 1970, 3, 5-9.
16. Wasserman, E. J. Chem. Phys. 1965, 42, 3739-3740.
17. Maier, G.; Reisenauer, H. P.; Schwab, W.; Cársky, P.; Špirko, V.; Hess, B. A.; Schaad, L. J. J. Chem. Phys. 1989, 91, 4763-4773.
18. DePinlo, J. T.; McMahon, R. J. J. Am. Chem. Soc. 1993, 115, 12573-12574.
19. Seburg, R. A.; DePinto, J. T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1995, 117, 835-836.
20. Seburg, R. A.; Patterson, E. V.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 1997, 119, 5847-5856.
21. Koga, N.; Matsumura, M.; Noro, M.; Iwamura, H. Chem. Lett. 1991, 1357-1360.
22. Noro, M.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1993, 115, 4916.
23. Noro, M.; Masuda, T.; Ichimura, A. S.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1994, 116, 6179-6190.
24. Bowling, N. P.; Halter, R. J.; Hodges, J. A.; Seburg, R. A.; Thomas, P. S.; Simmons, C. S.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 2006, 128, 3291-3302.
25. Hauptmann, H. Tetrahedron 1976, 32, 1293-1297.
26. Hori, Y.; Noda, K.; Kobayashi, S.; Taniguchi, H. Tetrahedron Lett. 1969, 3563-3566.
27. Jahn, H. A.; Teller, E. Proc. R. Soc. London, Ser. A 1937, 161, 220-235.
28. Hehre, W. J.; Pople, J. A.; Lathan, W. A.; Radom, L.; Wasserman, E.; Wasserman, Z. R. J. Am. Chem. Soc. 1976, 98, 4378-4383.
29. Herges, R.; Mebel, A. J. Am. Chem. Soc. 1994, 116, 8229-8237.
30. Fan, Q.; Pfeiffer, G. V. Chem. Phys. Lett. 1989, 162, 472-478.
31. Horný, L.; Petraco, N. D. K.; Schaefer, H. F., III. J. Am. Chem. Soc. 2002, 124, 14716-14720.
32. Seburg, R. A.; McMahon, R. J.; Stanton, J. F.; Gauss, J. J. Am. Chem. Soc. 1997, 119, 10838-10845.
33. Wierlacher, S.; Sander, W.; Marquardt, C.; Kraka, E.; Cremer, D. Chem. Phys. Lett. 1994, 222, 319-324.
34. Casey, C. P.; Kraft, S.; Powell, D. R. J. Am. Chem. Soc. 2002, 124, 2584-2594.
35. Casey, C. P.; Dzwiniel, T. L.; Kraft, S.; Guzei, I. A. Organometallics 2003, 22, 3915-3920.
36. Details are available as Supporting Information.
37. Plattner, D. A.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 4405-4406.
38. Woodcock, H. L.; Schaefer, H. F., III; Schreiner, P. R. J. Phys. Chem. A 2002, 106, 11923-11931.
39. Wentrup, C. Reactive Molecules; John Wiley: New York, 1984; p 333.
40. Wentrup, C. In Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme: Stuttgart, 1989; Vol. E19b, pp 824-1021.
41. Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535-1542.
42. Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 61, 7022-7029.
43. Schreiner, P. R.; Karney, W. L.; Schleyer, P. v. R.; Borden, W. T.; Hamilton, T. P.; Schaefer, H. F. J. Org. Chem. 1996, 61, 7030-7039.
44. McMahon, R. J.; Abelt, C. J.; Chapman, O. L.; Johnson, J. W.; Kreil, C. L.; LeRoux, J.-P.; Mooring, A. M.; West, P. R. J. Am. Chem. Soc. 1987, 109, 2456-2469.
45. Kuzaj, M.; Lüerssen, H.; Wentrup, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 480-482.
46. Weltner, W., Jr. Magnetic Atoms and Molecules; Van Nostrand Reinhold: New York, 1983.
47. Wertz, J. E.; Bolton, J. R. Electron Spin Resonance Spectroscopy; Chapman and Hall: New York, 1986.
48. Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 1993, 93, 1583-1621.
49. DePinto, J. T. Ph.D. Thesis; University of Wisconsin, Madison, WI. 1993.
50. Wasserman, E.; Kuck, V. J.; Yager, W. A.; Hutton, R. S.; Greene, F. D.; Abegg, V. P.; Weinshenker, N. M. J. Am. Chem. Soc. 1971, 93, 6335-6337.
51. Nazran, A. S.; Gabe, E. J.; LePage, Y.; Northcott, D. J.; Park, J. M.; Griller, D. J. Am. Chem. Soc. 1983, 105, 2912-2913.
52. Hu, Y.; Hirai, K.; Tomioka, H. J. Am. Chem. Soc. 1999, 103, 9280-9284.
53. Makarov, B. P.; Tomioka, H. Org. Biomol. Chem. 2004, 2, 1834-1837.
54. McMahon, R. J.; Chapman, O. L. J. Am. Chem. Soc. 1987, 109, 683-692.
55. Chapman, O. L.; Johnson, J. W.; McMahon, R. J.; West, P. R. J. Am. Chem. Soc. 1988, 110, 501-509.
56. Matzinger, S.; Bally, T. J. Phys. Chem. A 2000, 104, 3544-3552.
57. Maier, G.; Reisenauer, H. P.; Schwab, W.; Cársky, P.; Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1987, 109, 5183-5188.
58. Frisch, M. J.; et al. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
59. Frisch, M. J.; et al. Gaussian 03, revision B.05; Gaussian, Inc.: Wallingford, CT, 2004.
60. Becke, A. D. Phys. Rev. A: At. Mol. Opt. Phys. 1988, 38, 3098-3100.
61. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789.
62. Swanson, B. I.; Jones, L. H. J. Mol. Spectrosc. 1981, 89, 566-568.