Abstract
A good correlation has been established between the Brønsted coefficients βN u c and βo x for reactions of aryl-containing N-anions with various aryl halides. This correlation reflects the dependence of the internal barrier of aromatic nucleophilic substitution on the oxidation potentials of nucleophiles.
Similar content being viewed by others
REFERENCES
Kirk, R.E. and Othmer, D.F., Encyclopedia of Chemical Technology, New York: Wiley, 1992, vol. 2, p. 452.
Stern, M.K., Hileman, F.D., and Bashkin, J.K., J. Am. Chem. Soc., 1992, vol. 114,no. 23, p. 9237.
Hartwig, J.F, Angew. Chem., Int. Ed., 1998, vol. 37,no. 15, p. 2046.
Denny, D.B. and Denney, D.Z, Tetrahedron, 1991, vol. 47,no. 33, p. 6577.
Denny, D.B., Denney, D.Z, and Perez, A.J., Tetrahedron, 1993, vol. 49,no. 21, p. 4463.
Bunnett, J.F., Tetrahedron, 1993, vol. 49,no. 21, p. 4477.
Saveant, J.-M., Tetrahedron, 1994, vol. 50,no. 34, p. 10 117.
Balslev, H. and Lund, H., Tetrahedron, 1994, vol. 50,no. 26, p. 7889.
Marquet, J., Casado, F., Cervera, M., Espin, M., Gallardo, I., Mir, M., and Niat, M., Pure Appl. Chem., 1995, vol. 67,no. 5, p. 703.
Eberson, L., Acta Chem. Scand., Ser. B, 1984, vol. 38,no. 5, p. 439.
Bordwell, F.G. and Harrelson, J.A., J. Org. Chem., 1989, vol. 54,no. 20, p. 4893.
Lund, T. and Lund, H., Acta Chem. Scand., Ser. B, 1986, vol. 40,no. 6, p. 470.
Edwards, O., J. Am. Chem. Soc., 1954, vol. 76,no. 6, p. 1540.
Edwards, O., J. Am. Chem. Soc., 1956, vol. 78,no. 9, p. 1819.
Nucleophilicity, Harris, J.M. and McManus, S.P., Eds., Adv. Chem. Ser., Washington, 1987, no. 215, p. 137.
Bordwell, F.G., Clemens, A.H., Smith, D.E., and Begemann, J., J. Org. Chem., 1985, vol. 50,no. 8, p. 1151.
Vlasov, V.M., Os'kina, I.A., Landini, D., and Maia, A., Izv. Ross. Akad. Nauk, Ser. Khim., 1995, vol. 44,no. 12, p. 2211.
Vlasov, V.M., Os'kina, I.A., and Starichenko, V.F., Zh. Org. Khim., 1997, vol. 33,no. 5, p. 720.
Shalev, H. and Evans, D.H., J. Am. Chem. Soc., 1989, vol. 111,no. 8, p. 2667.
Bordwell, F.G. and Hughes, D.L., J. Am. Chem. Soc., 1986, vol. 108,no. 19, p. 5991.
Vlasov, V.M. and Os'kina, I.A., Zh. Org. Khim., 1994, vol. 30,no. 10, p. 1507.
Landini, D., Maia A., Secci, D., Vlasov, V.M., and Os'kina, I.A., New J. Chem., 1998, vol. 22,no. 1, p. 71.
Moutiers, G., Le Guevel, E., Cannes, C., Terrier, F., and Buncel, E., Eur. J. Org. Chem., 2001, no. 17, p. 3279.
Bordwell, F.G. and Hughes, D.L., J. Am. Chem. Soc., 1984, vol. 106,no. 11, p. 3234.
Pross, A.J., J. Org. Chem., 1984, vol. 49,no. 10, p. 1811.
Hoz, S., Acc. Chem. Res., 1993, vol. 26,no. 2, p. 69.
Terrier, F., Nucleophilic Aromatic Displacement: the Influence of the Nitro Group, New York: VCH, 1991, ch. 1, p. 21.
Bordwell, F.G. and Wilson, C.A., J. Am. Chem. Soc., 1987, vol. 109,no. 18, p. 5470.
Magdesieva, T.V., Kukhareva, I.I., Artamkina, G.A., Butin, K.P., and Beletskaya, I.P., Zh. Org. Khim., 1994, vol. 30,no. 4, p. 591.
Bordwell, F.G. and Bausch, M.J., J. Am. Chem. Soc., 1986, vol. 108,no. 8, p. 1985.
Bordwell, F.G., Bausch, M.J., and Wilson, C.A., J. Am. Chem. Soc., 1987, vol. 109,no. 18, p. 5465.
Zhang, X.-M., Yang, D.-L, and Liu, Y.-C., J. Org. Chem., 1993, vol. 58,no. 1, p. 224.
Zhang, X.-M., Yang, D.-L., Jia, X.-Q., and Liu, Y.-C., J. Org. Chem., 1993, vol. 58,no. 26, p. 7350.
Makosza, M., Podraza, R., and Kwast, A., J. Org. Chem., 1994, vol. 59,no. 22, p. 6796.
Tanko, J.M. and Brammer, L.E., Jr., J. Org. Chem., 1997, vol. 62,no. 16, p. 5550.
Marcus, R.A., J. Phys. Chem., 1963, vol. 67,no. 4, p. 853.
Vlasov, V.M. and Yakobson, G.G., Zh. Org. Khim., 1981, vol. 17,no. 10, p. 2192.
Os'kina, I.A. and Vlasov, V.M., Zh. Org. Khim., 2001, vol. 37,no. 2, p. 273.
Os'kina, I.A. and Vlasov, V.M., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., 1984, issue 4, no. 10, p. 102.
Chambers, R.D., Musgrave, W.C.R., Sargent, C.R., and Drakesmith, F.G., Tetrahedron, 1981, vol. 37,no. 3, p. 591.
Tsingarelyan, R.D., Kan'shina, E.A., and Tabakova, O.M., Zh. Anal. Khim., 1981, vol. 36,no. 8, p. 1557.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Vlasov, V.M., Os'kina, I.A. Linear Free Energy Relationships in SNAr Reactions of Aryl and Diaryl N-Anions with Aryl Halides. Russian Journal of General Chemistry 74, 600–605 (2004). https://doi.org/10.1023/B:RUGC.0000031864.05199.b2
Issue Date:
DOI: https://doi.org/10.1023/B:RUGC.0000031864.05199.b2