

11. Electronic effects of nitro, nitroso, amino and related groups |
529 |
142.M. Charton, in Reference 76. Chap. 11.
143.M. H. Aslam, A. G. Burden, N. B. Chapman, J. Shorter and M. Charton, J. Chem. Soc., Perkin Trans. 2, 500 (1981).
144.M. H. Aslam, N. B. Chapman, J. Shorter and M. Charton, J. Chem. Soc., Perkin Trans. 2, 720 (1981).
145.Reference 5, pp. 433 436.
146.M. H. Aslam, Ph.D. thesis, University of Hull, 1978. Also deposited material associated with References 143 and 144.
147.M. Kurahashi, M. Fukuyo and A. Shimada, Bull Chem. Soc. Jpn., 40, 1296 (1967).
148.N. B. Chapman, J. R. Lee and J. Shorter, J. Chem. Soc. (B), 769 (1969).
149.N. B. Chapman, J. R. Lee and J. Shorter, J. Chem. Soc. (B), 755 (1970).
150.C. Hansch, A. Leo and R. W. Taft, Chem. Rev., 91, 165 (1991).
151.R. W. Taft and R. D. Topsom, Prog. Phys. Org. Chem., 16, 1 (1987).
152.R. W. Taft, J. Phys. Chem., 64, 1805 (1960).
153.Y. Yukawa, Y. Tsuno and M. Sawada, Bull. Chem. Soc. Jpn., 45, 1198 (1972).
154.R. T. C. Brownlee, R. E. J. Hutchison, A. R. Katritzky, T. T. Tidwell and R. D. Topsom, J. Am. Chem. Soc., 90, 1757 (1968).
155.J. Bromilow, R. T. C. Brownlee, V. O. Lopez and R. W. Taft, J. Org. Chem., 44, 4766 (1979).
156.W. F. Reynolds, A. Gomes, A. Maron, D. W. MacIntyre, A. Tanin, G. K. Hamer and I. R. Peat, Can. J. Chem., 61, 2376 (1983).
157.D. A. R. Happer, J. Chem. Soc., Perkin Trans. 2, 1673 (1984).
158.C. Laurence, M. Berthelot, M. Lu¸con, M. Helbert, D. G. Morris and J. -F. Gal, J. Chem. Soc., Perkin Trans. 2, 705 (1984).
159.C. Laurence, in Reference 76, Chap. 5.
160.G. G. Smith and F. W. Kelly, Prog. Phys. Org. Chem., 8, 75 (1971).
161.K. A. Holbrook, in Supplement B2: The Chemistry of Acid Derivatives, Vol. 2 (Ed. S. Patai), Chap. 12, Wiley, Chichester, 1992.
162.R. Taylor, in Supplement B: The Chemistry of Acid Derivatives (Ed. S. Patai), Wiley, Chichester, 1979, p. 860.
163.M. Mashima, R. T. McIver, R. W. Taft, F. G. Bordwell and W. N. Olmstead, J. Am. Chem. Soc., 106, 2717 (1984).
164.S. Marriott and R. D. Topsom, J. Am. Chem. Soc., 106, 7 (1984).
165.S. Marriott and R. D. Topsom, J. Chem. Soc., Perkin Trans. 2, 1045 (1985).
166.S. Marriott, A. Silvestro and R. D. Topsom, J. Chem. Soc., Perkin Trans. 2, 457 (1988).
167.S. Marriott, A. Silvestro and R. D. Topsom, J. Mol. Struct. (Theochem), 184, 23 (1989).
168.Cai Jinfeng and R. D. Topsom, J. Mol. Struct. (Theochem), 204, 353 (1990).
169.Jinfeng Cai and R. D. Topsom, J. Mol. Struct. (Theochem), 228, 181 (1991).
170.Tony Silvestro and R. D. Topsom, J. Mol. Struct. (Theochem), 206, 309 (1990).
171.R. D. Topsom, Prog. Phys. Org. Chem., 17, 107 (1990).
172.R. D. Topsom, Prog. Phys. Org. Chem., 16, 125 (1987).
173.T. Sotomatsu, Y. Murata and T. Fujita, J. Comput. Chem., 10, 94 (1989).
174.K. H. Kim and Y. C. Martin, J. Org. Chem., 56, 2723 (1991).
175.V. I. Galkin, A. R. Cherkasov, R. D. Sayakhov and R. A. Cherkasov, Zh. Obshch. Khim., 65, 458, 469, 474 (1995).
176.O. Pytela, Collect. Czech. Chem. Commun., 59, 159 (1994).
177.O. Pytela, Collect. Czech. Chem. Commun., 59, 381 (1994).
˘´
178.O. Pytela, J. Kulhanek,´ M. Ludwig and V. Riha, Collect. Czech. Chem. Commun., 59, 627 (1994).
179.O. Pytela, J. Kulhanek´ and M. Ludwig, Collect. Czech. Chem. Commun., 59, 1637 (1994).
180.O. Pytela and J. Liska,˘ Collect. Czech. Chem. Commun., 59, 2005 (1994).
181.Published since 1965 by Wiley. The latest volume is Organic Reaction Mechanisms 1993 (Eds. A. C. Knipe and W. E. Watts), Wiley, Chichester, 1995.
182.Reference 107c, Volume II, Part 1 and Supplementary Volume I, Issue 5.
183.F. G. Bordwell, Acc. Chem. Res., 21, 456 (1988) and references cited therein.
184.J. R. Jones, The Ionizatiom of Carbon Acids, Chap. 5, Academic Press, London, 1973.
185.D. J. Cram, Fundamentals of Carbanion Chemistry, Academic Press, New York, 1965.
186.R. P. Bell, The Proton in Chemistry, 2nd edn., Chapman and Hall, London, 1973.
187.J. R. Gandler and C. F. Bernasconi, J. Am. Chem. Soc., 114, 631 (1992).
188.F. Terrier, T. Boubaker, L. Xiao and P. G. Farrell, J. Org. Chem., 57, 3924 (1992).

530 |
John Shorter |
189.F. Terrier, L. Xiao, P. G. Farrell and D. Moskowitz, J. Chem. Soc., Perkin Trans. 2, 1259 (1992).
190.A. Jarczewski, G. Schroeder and K. T. Leffek, Can. J. Chem., 69, 468 (1991).
191.M. Amin and W. H. Saunders, J. Phys. Org. Chem., 6, 393 (1993).
192.K. Bowden, A. F. Cockerill and J. R. Gilbert, J. Chem. Soc. (B), 179 (1970).
193.S. Bradamente and G. A. Pagani, J. Org. Chem., 45, 105, 114 (1980).
194.S. Bradamente and G. A. Pagani, J. Chem. Soc., Perkin Trans. 2, 1047 (1986).
195.A. Abbotto, S. Bradamente and G. A. Pagani, J. Org. Chem., 58, 449 (1993).
196.C. A. Bunton, Nucleophilic Substitution at a Saturated Carbon Atom, Elsevier, Amsterdam, 1963.
197.J. Miller, Aromatic Nucleophilic Substitution, Elsevier, Amsterdam, 1968.
198.Unless a more specific reference is given, rate coefficients in Section VI.B have been taken from the volumes of Reference 107c: Volume 3, Part 1 (first order nucleophilic substitution); Volume 4, Part 2 (aromatic nucleophilic substitution).
199.W. F. Reynolds, P. Dais, D. W. Macintyre, R. D. Topsom, S. Marriott, E. von Nagy-Felsobuki and R. W. Taft, J. Am. Chem. Soc., 105, 378 (1983).
200.P. G. Gassman and J. J. Talley, J. Am. Chem. Soc., 102, 1214 (1980).
201.P. G. Gassman and T. T. Tidwell, Acc. Chem. Res., 16, 279 (1983).
202.T. T. Tidwell, Angew. Chem., Int. Ed. Engl., 23, 20 (1984).
203.A. D. Allen, V. M. Kanagasabapathy and T. T. Tidwell, J. Am. Chem. Soc., 108, 3470 (1986).
204.G. A. Olah, G. K. S. Prakash, M. Arvanaghi, V. V. Krishnamurthy and S. C. Narang, J. Am. Chem. Soc., 106, 2378 (1984).
205.A. Fischer, W. J. Galloway and J. Vaughan, J. Chem. Soc., 3591, 3596 (1964).
206.C. D. Johnson, I. Roberts and P. G. Taylor, J. Chem. Soc., Chem. Commun., 897 (1977).
207. M. Taagapera, K. D. Summerhays, W. J. Hehre, R. D. Topsom, A. Pross, L. Radom and
R. W. Taft, J. Org. Chem., 46, 891 (1981).
208.N. B. Chapman and D. A. Russell-Hill, J. Chem. Soc., 1563 (1956).
209.Reference 197, p. 23.
210.N. B. Chapman, D. K. Chaudhury and J. Shorter, J. Chem. Soc., 1975 (1962).
211.D. M. Brewis, N. B. Chapman, J. S. Paine, J. Shorter and D. J. Wright, J. Chem. Soc., Perkin Trans. 2, 1787 (1974).
212.D. M. Brewis, N. B. Chapman, J. S. Paine and J. Shorter, J. Chem. Soc., Perkin Trans. 2, 1802 (1974).
213.J. Miller and A. J. Parker, Aust. J. Chem., 11, 302 (1958).
214.Reference 197, p. 100.
215.E. Buncel and R. A. Manderville, J. Phys. Org. Chem., 6, 71 (1993).
216.F. Terrier, M. -J. Pouet, J. -C. Halle, S. Hunt, J. R. Jones and E. Buncel, J. Chem. Soc., Perkin Trans. 2, 1665 (1993).
217.C. A. Grob and M. G. Schlageter, Helv. Chim. Acta, 60, 1884 (1977).
218.C. A. Grob and M. G. Schlageter, Helv. Chim. Acta, 59, 264 (1976).
219.W. Fischer and C. A. Grob, Helv. Chim. Acta, 61, 1588 (1978).
220.C. A. Grob and A. Waldner, Helv. Chim. Acta, 62, 1736 (1979).
221.C. A. Grob and R. Rich, Helv. Chim. Acta, 62, 2793 (1979).
222.C. A. Grob, Angew. Chem., Int. Ed. Engl., 15, 569 (1979).
223.R. Taylor, Electrophilic Aromatic Substitution, Wiley, Chichester, 1990.
224.Reference 223, pp. 308, 395 and 485 487.
225.Reference 223, pp. 143 154.
226.Reference 223, pp. 154 156.
227.Reference 223, pp. 346 347.
228.Reference 223, pp. 458 463.
229.From Table 16 in G. E. K. Branch and M. Calvin, The Theory of Organic Chemistry, PrenticeHall, New York, 1946, p. 146.
230.F. S. Fawcett and W. A. Sheppard, J. Am. Chem. Soc., 87, 4341 (1965).
231.E. Yu. Belyaev, M. S. Tovbis and G. A. Suboch, Zh. Org. Khim., 12, 1826 (1976); English edition, 12, 1790 (1976).
232.Reference 197, pp. 79 81.
233.M. M. Fickling, A. Fischer, B. R. Mann, J. Packer and J. Vaughan, J. Am. Chem. Soc., 81, 4226 (1959).
234.Reference 6, pp. 269 272.
235.E. P. Serjeant, Aust. J. Chem., 22, 1189 (1969).
11. Electronic effects of nitro, nitroso, amino and related groups |
531 |
236.B. van de Graaf, A. J. Hoefnagel and B. M. Wepster, J. Org. Chem., 46, 653 (1981).
237.O. Exner and J. Lakomy,´ Collect. Czech. Chem. Commun., 35, 1371 (1970).
238.E. N. Tsvetkov, D. I. Lobanov, M. M. Makhamatkhanov and M. I. Kabachnik, Tetrahedron, 25, 5623 (1969).
239.A. J. Hoefnagel, M. A. Hoefnagel and B. M. Wepster, J. Am. Chem. Soc., 98, 6194 (1976).
240. |
´ |
O. Exner and M. Bude˘s˘insky,´ Magn. Reson. Chem., 27, 27 (1989). |
|
241. |
´ |
M. Bude˘s˘insky´ and O. Exner, Magn. Reson. Chem., 27, 585 (1989). |
|
242. |
M. Ludwig, S. Wold and O. Exner, Acta Chem. Scand., 46, 549 (1992). |
243. |
O. Exner and T. M. Krygowski are in the course of publishing an article on the nitro group as |
|
a substituent, in which various issues about its electronic effect are addressed. |
244. |
C. G. Swain and E. C. Lupton, J. Am. Chem. Soc., 90, 4328 (1968). |
245. |
C. Hansch, A. Leo, S. H. Unger, K. H. Kim, D. Nakaitani and E. J. Lien, J. Med. Chem., 16, |
|
1207 (1973). |
246. |
C. G. Swain, S. H. Unger, N. R. Rosenquist and M. S. Swain, J. Am. Chem. Soc., 105, 492 |
|
(1983). |
247. |
W. F. Reynolds and R. D. Topsom, J. Org. Chem., 49, 1989 (1984). |
248. |
A. J. Hoefnagel, W. Oosterbeek and B. M. Wepster, J. Org. Chem., 49, 1993 (1984). |
249. |
M. Charton, J. Org. Chem., 49, 1997 (1984). |
250. |
C. G. Swain, J. Org. Chem., 49, 2005 (1984). |
251. |
C. Hansch, in Reference 78, Chap. 9. |
252. |
W. J. Hehre, C. -F. Pau, A. D. Headley, R. W. Taft and R. D. Topsom, J. Am. Chem. Soc., 108, |
|
1711 (1986). |
253. |
J. -L. M. Abboud, J. Catalan,´ J. Elguero and R. W. Taft, J. Org. Chem., 53, 1137 (1988). |
254. |
R. W. Taft, J. L. M. Abboud, F. Anvia, M. Berthelot, M. Fujio, J. -F. Gal, A. D. Headley, |
|
W. G. Henderson, I. Koppel, J. H. Qian, M. Mishima, M. Taagepera and S. Ueji, J. Am. Chem. |
|
Soc., 110, 1797 (1988). |
255.M. Charton, Prog. Phys. Org. Chem., 16, 287 (1987).
256.M. Charton and B. Charton, Bull. Soc. Chim. France, 199 (1988).
257.Reference 255, p. 238.