Substituent effects on stability and isomerization energies of isocyanides and nitriles

Journal of Organic Chemistry

Volumn 64, Issue 25, 1999, Pages 8984-8989

  Sung, Kuangsen ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; ISOCYANIC ACID DERIVATIVE; LITHIUM; MAGNESIUM DERIVATIVE; NITRILE; SODIUM;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENTHALPY; ISOMERISM; MOLECULAR STABILITY; REACTION ANALYSIS;

EID: 0032784875     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9910583     Document Type: Article

References (47)

1. (a) Tidwell, T. T. Ketenes; Wiley: New York, 1996.
2. (b) Gong, L.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1991, 113, 6021.
3. (c) McAllister, M. A.; Tidwell, T. T. J. Org. Chem. 1994, 59, 4506.
4. (d) McAllister, M. A.; Tidwell, T. T. J. Chem. Soc., Perkin Trans. 2 1994, 2239.
5. (a) Furet, P.; Matcha, R. L.; Fuchs, R. J. Phys. Chem. 1986, 90, 5571.
6. (b) Lambert, C.; Schleyer, P. v. R.; Wurthwein, E.-U. J. Org. Chem. 1993, 58, 6377.
7. (a) Greenberg, A.; Stevenson, T. A. J. Am. Chem. Soc. 1985, 107, 3488.
8. (b) Clark, T.; Spitznagel, G. W.; Klose, R.; Schleyer, P. v. R. J. Am. Chem. Soc. 1984, 106, 4412.
9. (c) Wiberg, K. B.; Laidig, K. E. J. Org. Chem. 1992, 57, 5092.
10. (d) Cremer, D.; Kraka, E. J. Am. Chem. Soc. 1985, 107, 3811.
11. (a) Liang, C.; Allen, L. C. J. Am. Chem. Soc. 1991, 113, 1878.
12. (b) Muller-Remmers, P. L.; Jug, K. J. Am. Chem. Soc. 1985, 107, 7275.
13. (c) Goodman, J. M.; James, J. J.; Whiting, A. J. Chem. Soc., Perkin Trans. 2 1994, 109.
14. (d) Wang, F.; Winnik, M. A.; Peterson, M. P.; Csizmadia, I. G. THEOCHEM 1991, 232, 203.
15. (e) Kahn, S. D.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1987, 109, 1871.
16. (a) Heinrich, N.; Koch, W.; Frenking, G.; Schwarz, H. J. Am. Chem. Soc. 1986, 108, 593.
17. (b) Dill, J. D.; Greenberg, A.; Liebman, J. F. J. Am. Chem. Soc. 1879, 101, 6814.
18. (a) Wiberg, K. B.; Rosenberg, R. E. J. Am. Chem. Soc. 1990, 112, 1509.
19. (b) Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. J. Am. Chem. Soc. 1992, 114, 8644.
20. White, J. C.; Cave, R. J.; Davidson, E. R. J. Am. Chem. Soc. 1988, 110, 6308.
21. Sung, K. J. Chem. Soc., Perkin Trans. 2, in press.
22. (a) Ruchardt, C.; Meier, M.; Haaf, K.; Pakusch, J.; Wolber, E. K. A.; Muller, B. Angew. Chem., Int. Ed. Engl. 1991, 30, 893.
23. (b) Ugi, I. Isocyanide Chemistry; Academic Press: New York, 1971.
24. (a) Rigby, J. H.; Laurent, S. J. Org. Chem. 1998, 63, 6742.
25. (b) Shaabani, A.; Farrokhzad, F. J. Chem. Res., Synop. 1997, 344.
26. (c) Nguyen, P. T.; Palmer, W. S.; Woerpel, K. A. J. Org. Chem. 1999, 64, 1843.
27. (d) Lentz, D. Z. Naturforsch 1992, 47b, 148.
28. (e) Yavari, I.; Heydari, M.; Nori-Shargh, D. J. Chem. Res., Synop. 1994, 384.
29. (f) Meot-Ner, M.; Sieck, W.; Koretke, K. K.; Deakyne, C. A. J. Am. Chem. Soc. 1997, 119, 10430.
30. (a) Sumathi, R.; Nguyen, M. T. J. Phys. Chem. A 1998, 102, 412.
31. (b) Shen, D.; Pritchard, H. O. J. Phys. Chem. 1994, 98, 1743.
32. (a) Casanova, J., Jr.; Werner, N. D.; Schuster, R. E. J. Org. Chem. 1966, 31, 3473.
33. (b) Meier, M.; Muller, B.; Ruchardt, C. J. Org. Chem. 1987, 52, 648.
34. (c) Kim, S. S.; Choi, W. J.; Zhu, Y.; Kim, J. H. J. Org. Chem. 1998, 63, 1185.
35. (d) Meier, M.; Dogan, B.; Beckhaus, H.-D.; Ruchardt, C. New J. Chem. 1987, 11, 2.
36. (a) Hertler, W. R.; Dixon, D. A.; Matthews, E. W.; Davidson, F.; Kitson, F. G. J. Am. Chem. Soc. 1987, 109, 6532.
37. (b) Arnold, D. E. J.; Cradock, S.; Ebsworth, E. A. V.; Murdoch, J. D.; Rankin, D. W. H.; Skea, D. C. J.; Harris, R. K.; Kimber, B. J. J. Chem. Soc., Dalton Trans. 1981, 1349.
38. (c) Georgiou, K.; Legon, A. C. J. Mol. Struct. 1982, 78, 257.
39. Isaacs, N. Physical Organic Chemistry, 2nd ed.; Longman Scientific & Technical: Essex, England, 1995.
40. Ehrenson, S.; Brownlee, R. J. C.; Taft, R. W. Prog. Phys. Org. Chem. 1973, 10, 1.
41. (b) Topsom, R. D. Prog. Phys. Org. Chem. 1976, 12, 1.
42. (a) Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996.
43. (b) George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Tetrahedron 1976, 32, 317.
44. (c) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Pertersson, G. A.; Montgomery, J. A.; Raghavachari, K.; AlLaham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A. Gaussian94, Revision D2; Gaussian, Inc., Pittsburgh, PA, 1995.
46. Charton, M. Prog. Phys. Org. Chem. 1981, 13, 119.
47. Baghai-Vayjovee, M. H.; Collister, J. L.; Pritchard, H. O. Can. J. Chem. 1977, 55, 2634.