Y-aromaticity: Why is the trimethylenemethane dication more stable than the butadienyl dication?

Journal of Organic Chemistry

Volumn 70, Issue 19, 2005, Pages 7605-7616

  Dworkin, Amy ^a   Naumann, Rachel ^a   Seigfred, Christopher ^a   Karty, Joel M ^a   Mo, Yirong ^b  

^a ELON UNIVERSITY   (United States)

^b WESTERN MICHIGAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL BONDS; CONFORMATIONS; METHANE; POSITIVE IONS; PROBABILITY DENSITY FUNCTION; PROPYLENE; RESONANCE;

BUTADIENYL; ORBITAL DELETION PROCEDURE (ODP); TRIMETHYLMETHANE; Y-AROMATICITY;

AROMATIC COMPOUNDS;

1,3 BUTADIENE; 2 BUTENE; CARBON; METHANE; METHYLPROPENE; TRIMETHYLENEMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENERGY; ENTHALPY; METHODOLOGY; MOLECULAR STABILITY; STRUCTURE ANALYSIS;

EID: 24944569251     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0508090     Document Type: Article

References (59)

1. Klein, J.; Medlik, A. J. Chem. Soc., Chem. Commun. 1973, 275.
2. Bates, W. A.; Beaven, W. A.; Greene, M. G.; Klein, J. H. J. Am. Chem. Soc. 1974, 96, 5640.
3. Klein, J.; Medlik-Balan, A.; Meyer, A. Y.; Chorev, M. Tetrahedron 1976, 32.
4. Gund, P. J. Chem. Educ. 1972, 49, 100.
5. Finnegan, R. A. Ann. N. Y. Acad. Sci. 1969, 159, 242-266.
6. Note: we have repeated the Hückel calculations here and arrived at 0.228 β greater resonance stabilization in both Y-shaped ions.
7. Agranat, I.; Skancke, A. J. Am. Chem. Soc. 1985, 107, 867.
8. Krygowski, T. M.; Cyranski, M. K.; Anulewics-Ostrowska, R. Pol. J. Chem. 2001, 75, 1939-1942.
9. Mills, N. S.; Shapiro, J.; Hollingsworth, M. J. Am. Chem. Soc. 1981, 103, 1263.
10. Rajca, A.; Tolbert, L. M. J. Am. Chem. Soc. 1985, 107, 698-699.
11. Radhakrishnan, T. P.; Agranat, I. J. Org. Chem. 2001, 66, 3215.
12. Agranat, I.; Radhakrishnan, T. P.; Herndon, W. C.; Skancke, A. Chem. Phys. Lett. 1991, 181, 117.
13. Skancke, A. J. Phys. Chem. 1994, 98, 5234-5239.
14. Sommerfeld, T. J. Am. Chem. Soc. 2002, 124, 1119-1124.
15. Wiberg, K. B. J. Am. Chem. Soc. 1990, 112, 4177.
16. Gobbi, A.; Frenking, G. J. Am. Chem. Soc. 1993, 115, 2362-2372.
17. Lowry, T. H.; Richardson, K. S. Mechanism and Theory In Organic Chemistry, 3rd ed.; HarperCollins: New York, 1987.
18. Barbour, J. B.; Karty, J. M. J. Org. Chem. 2004, 69, 648.
19. Holt, J.; Karty, J. M. J. Am. Chem. Soc. 2003, 125, 2797.
20. Wheland, G. W. The Theory of Resonance; John Wiley & Sons: New York, 1944.
21. Barbour, J. B.; Karty, J. M. J. Phys. Org. Chem. 2005, 18, 210-216.
22. Hiberty, P. C.; Byrman, C. P. J. Am. Chem. Soc. 1995, 117, 9875-9880.
23. Mo, Y.; Zhenyang, L.; Wu, W.; Zhang, Q. J. Phys. Chem. 1996, 100, 6469.
24. Mo, Y.; Lin, Z. J. Chem. Phys. 1996, 105, 1046-1051.
25. Mo, Y.; Schleyer, P. v. R.; Jiao, H.; Lin, Z. Chem. Phys. Lett. 1997, 280, 439-443.
26. Mo, Y.; Jiao, H.; Lin, Z.; Schleyer, P. v. R. Chem. Phys. Lett. 1998, 289, 383-390.
27. Mo, Y.; M., L.; Wu, W.; Zhang, Q.; Schleyer, P. v. R. Sci. China, Ser. B 1999, 42, 253-260.
28. Mo, Y.; Wu, W.; Zhang, Q. J. Chem. Phys. 2003, 119, 6448-6456.
29. Mo, Y.; Jiao, H.; Schleyer, P. v. R. J. Org. Chem. 2004, 69, 3493-3499.
30. Mo, Y.; Peyerimhoff, S. D. J. Chem. Phys. 1998, 109, 1687.
31. Mo, Y.; Zhang, Y.; Gao, J. J. Am. Chem. Soc. 1999, 121, 5737-5742.
32. Mo, Y.; Gao, J.; Peyerimhoff, S. D. J. Chem. Phys. 2000, 112, 5530-5538.
33. Mo, Y.; Subramanian, G.; Ferguson, D. M.; Gao, J. J. Am. Chem. Soc. 2002, 124.
34. Mo, Y.; Song, L.; Wu, W.; Zhang, Q. J. Am. Chem. Soc. 2004, 126, 3974-3982.
35. Mo, Y. J. Org. Chem. 2004, 69, 5563-5567.
36. Mo, Y.; Gao, J. J. Phys. Chem. A 2000, 104, 3012-3020.
37. Mo, Y.; Gao, J. J. Comput. Chem. 2000, 21, 1458-1469.
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Gaussian, Inc.: Pittsburgh, PA, 1998.
39. (a) Becke, A. D. J. Chem. Phys., 98, 5648-5652.
40. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
41. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206.
42. Barbour, J. B.; Karty, J. M. J. Phys. Org. Chem., in press.
43. Radhakrishnan and Agranat (J. Org. Chem. 2001, 66, 3215) report the value to be between 8.2 and 9.2 kcal/mol using MP2, MP4, and B3LYP calculations.
44. Brauman, J. I.; Blair, L. K. J. Am. Chem. Soc. 1970, 92, 5986.
45. Schaad, L. J.; Hess, B. A. J. J. Am. Chem. Soc. 1972, 94, 3068.
46. Hess, B. A. J.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7500.
47. Bianchi, G.; Howarth, O. W.; Samuel, C. J.; Vlahov, G. J. Chem. Soc., Perkin Trans. 2 1995, 7, 1427-1432.
48. Mo, Y. J. Chem. Phys. 2003, 119, 1300-1306.
49. NBO 3.0: Glendening, E. D. R., A. E., Carpenter, J. E., Weinhold, F., Department of Chemistry, University of Wisconsin: Madison, WI.
50. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102.
51. Cooper, D. L.; Geratt, J.; Ralmondt, M. Nature 1986, 323, 699-701.
52. Shaik, S. S.; Hiberty, P. C.; Lefour, J. M.; Ohanessian, G. J. Am. Chem. Soc. 1987, 109, 363-374.
53. Janoschek, R. THEOCHEM 1991, 75, 197-302.
54. Matsunaga, N.; Cundari, T. R.; Schmidt, M. W.; Gordon, M. S. Theor. Chim. Acta 1992, 83, 57-68.
55. van Lenthe, J. H.; Havenith, R. W. A.; Dijkstra, F.; Jenneskens, L. W. Chem. Phys. Lett. 2002, 361, 203-208.
56. Mo, Y.; Wu, W.; Zhang, Q. J. Phys. Chem. 1994, 98, 10048-10053.
57. Behrens, S.; Koester, A. M.; Jug, K. J. Org. Chem. 1994, 59, 2546-2551.
58. Suresh, C. H.; Koga, N. J. Org. Chem. 2002, 67, 1965-1968.
59. Bartmess, J. E. In NIST Chemistry WebBook, NIST Standard Reference Database 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 1998.