Experimental determination of the heat of hydrogenation of phenylcyclobutadiene

Journal of the American Chemical Society

Volumn 127, Issue 37, 2005, Pages 13065-13069

  Fattahi, Alireza ^a   Lis, Lev ^a   Kass, Steven R ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DISSOCIATION; HYDROGENATION; POSITIVE IONS; THERMODYNAMICS;

1-PHENYLCYCLOBUTEN-3-YL CATION; DESTABILIZATION ENERGY; HEAT OF HYDROGENATION; PHENYLCYCLOBUTADIENE;

ORGANIC COMPOUNDS;

1 PHENYLCYCLOBUTEN 3 YL; 1 PHENYLCYCLOBUTENE; 1,3 BUTADIENE DERIVATIVE; CARBON; CATION; CYCLOBUTADIENE; CYCLOBUTANE DERIVATIVE; HYDROGEN; PHENYL GROUP; PHENYLCYCLOBUTADIENE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; DISSOCIATION; ENERGY; GAS; HEAT; HYDROGEN BOND; HYDROGENATION; MEASUREMENT; TECHNIQUE; THERMODYNAMICS;

CYCLOBUTANES; HEAT; HYDROGENATION; MOLECULAR STRUCTURE; THERMODYNAMICS;

EID: 25144441738     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0525511     Document Type: Article

References (61)

1. Bally, T.; Masamune, S. Tetrahedron 1980, 36, 343-370.
2. Maier, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 425-490.
3. Maier, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 309-332.
4. Pong, R. G. S.; Huang, B. S.; Laureni, J.; Krantz, A. J. Am. Chem. Soc. 1977, 99, 4153-4154.
5. Krantz, A.; Lin, C. Y.; Newton, M. D. J. Am. Chem. Soc. 1973, 95, 2744-2746.
6. Lin, C. Y.; Krantz, A. J. Chem. Soc., Chem. Commun. 1972, 1111-1112.
7. Chapman, O. L.; Pacansky, J.; Wojtkowski, P. W. J. Chem. Soc., Chem. Commun. 1973, 681-682.
8. Chapman, O. L.; De la Cruz, D.; Roth, R.; Pacansky, J. J. Am. Chem. Soc. 1973, 95, 1337-1338.
9. Chapman, O. L.; McIntosh, C. L.; Pacansky, J. J. Am. Chem. Soc. 1973, 95, 614-617.
10. Maier, G.; Pfriem, S.; Schaefer, U.; Malsch, K. D.; Matusch, R. Chem. Ber. 1981, 114, 3965-3987.
11. Maier, G.; Pfriem, S.; Schaefer, U.; Matusch, R. Angew. Chem. 1978, 90, 552-553.
12. Cram, D. J.; Tanner, M. E.; Thomas, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1024-1027.
13. Broadus, K. M.; Kass, S. R. J. Am. Chem. Soc. 2000, 122, 10697-10703.
14. Deniz, A. A.; Peters, K. S.; Snyder, G. J. Science 1999, 286, 1119-1122.
15. Bauld, N. L.; Welsher, T. L.; Cessac, J.; Holloway, R. L. J. Am. Chem. Soc. 1978, 100, 6920-6924.
16. Glukhovtsev, M. N.; Bach, R. D.; Laiter, S. THEOCHEM 1997, 417, 123-129.
17. Kovacevic, B.; Baric, D.; Maksic, Z. B.; Muller, T. J. Phys. Chem. A 2004, 108, 9126-9133.
18. Murray, J. S.; Seminario, J. M.; Politzer, P. Int. J. Quantum Chem. 1994, 49, 575-579.
19. Politzer, P.; Grice, M. E.; Murray, J. S.; Seminario, J. M. Can. J. Chem. 1993, 71, 1123-1127.
20. Dewar, M. J. S.; Kollmar, H. W. J. Am. Chem. Soc. 1975, 97, 2933-2934.
21. Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 6941-6955.
22. Kollmar, H. J. Am. Chem. Soc. 1980, 102, 2617-2621.
23. Kollmar, H.; Carrion, F.; Dewar, M. J. S.; Bingham, R. C. J. Am. Chem. Soc. 1981, 103, 5292-5303.
24. Haddon, R. C. Pure Appl. Chem. 1982, 54, 1129-1142.
25. Disch, R. L.; Schulman, J. M.; Sabio, M. L. J. Am. Chem. Soc. 1985, 107, 1904-1906.
26. Hess, B. A., Jr.; Allen, W. D.; Michalska, D.; Schaad, L. J.; Schaefer, H. F., III. J. Am. Chem. Soc. 1987, 109, 1615-1621.
27. Staley, S. W.; Norden, T. D. J. Am. Chem. Soc. 1989, 111, 445-449.
28. Glukhovtsev, M. N.; Laiter, S.; Pross, A. J. Phys. Chem. 1995, 99, 6828-6831.
29. Glukhovtsev, M. N.; Laiter, S.; Pross, A. J. Phys. Chem. 1996, 100, 17801-17806.
30. Rogers, D. W.; McLafferty, F. J.; Podosenin, A. V. J. Phys. Chem. 1996, 100, 17148-17151.
31. Hrouda, V.; Roeselova, M.; Bally, T. J. Phys. Chem. A 1997, 101, 3925-3935.
32. Pan, J.-W.; Rogers, D. W.; McLafferty, F. J. THEOCHEM 1999, 468, 59-66.
33. Jursic, B. S. THEOCHEM 2000, 507, 185-192.
34. Wiberg, K. B. Chem. Rev. 2001, 101, 1317-1331.
35. Feng, Y.; Liu, L.; Wang, J.-T.; Zhao, S.-W.; Guo, Q.-X. J. Org. Chem. 2004, 69, 3129-3138.
36. Kovacevic, B.; Baric, D.; Maksic, Z. B.; Mueller, T. J. Phys. Chem. A 2004, 108, 9126-9133.
37. George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Theor. Chim. Acta 1975, 38, 121-129.
38. George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Tetrahedron 1976, 32, 317-323.
39. Glasovac, Z.; Eckert-Maksic, M.; Dacres, J. E.; Kass, S. R. J. Chem. Soc. Perkin Trans. 2 2002, 410-415.
40. Frimer, A. A.; Pizem, H. Tetrahedron 1999, 55, 12175-12186.
41. Hassner, A.; Dillon, J. L., Jr. J. Org. Chem. 1983, 48, 3382-3386.
42. Manatt, S. L.; Vogel, M.; Knutson, D.; Roberts, J. D. J. Am. Chem. Soc. 1964, 86, 2645-2653.
43. Qian, W.; Ruhin, Y. J. Org. Chem. 2002, 67, 7683-7687.
44. Wang, T. C. L.; Ricca, T. L.; Marshall, A. G. Anal. Chem. 1986, 58, 2935-2938.
45. Gauthier, J. W.; Trautman, T. R.; Jacobson, D. B. Anal. Chim. Acta 1991, 246, 211-225.
46. Frisch, M. J. et al. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003.
47. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
48. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
49. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023.
50. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764-7776.
51. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1999, 110, 4703-4709.
52. Bartmess, J. E. In NIST Chemistry WebBook: NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD 20899 (http://webbook.nist.gov).
53. Exact mass measurements were made to verify the elemental composition of the fragment ions.
54. Kollmar, H.; Carrion, F.; Dewar, M. J. S.; Bingham, R. C. J. Am. Chem. Soc. 1981, 103, 5292-5303.
55. Wiberg, K. B.; Marquez, M. J. Am. Chem. Soc. 1998, 120, 2932-2938.
56. -1.
57. This quantity was obtained using Benson's group equivalents approach. Cohen, N.; Benson, S. Chem. Rev. 1993, 93, 2419-2438.
58. Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: New York, 1970; pp 1-643.
59. The B3LYP value for BDE2 has been corrected for the apparent error in the computed energy of phenycyclobutadiene as indicated in ref 56.
60. -1.
61. Glasovac, Z.; Eckert-Maksic, M.; Kass, S. R. Unpublished results.