The values of the orders of the phenyl-nitrogen bonds were calculated by the molecular orbital linear combination of atomic orbital method for groups with different states of the nitrogen atom. A linear dependence ofρn-c onσc was found, and from it the value of the bond order for the ethylenimine group was obtained by interpolation:σ 1.279.
p- and m-Fluoro-substituted phenylcyclopropanes, phenyl epoxides, styrenes, phenylacetylenes, cumenes, and m-cyclopropylbenzoic acid were synthesized.
The Taft constants for the cyclopropyl, isopropyl, vinyl, ethynyl, and epoxide groups were determined according to the chemical shifts of F19 in the NMR spectra. The constants of the cyclopropyl group were also obtained from pK of p- and m-cyclopropylbenzoic acids.
KeywordsPhenyl Vinyl Styrene Nitrogen Atom Epoxide
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- 1.V. F. Bystrov, R. G. Kostyanovskii, O. A. Pan'shin, A. U. Scepanyants, and O. A. Yuzhakova, Optika i Spektroskopiya,19, No. 2, 217 (1965); R. G. Kostyanovskii, O. A. Yuzhakova, and V. F. Bystrov, Zh. Vses. khim. obshch. im. D. I. Mendeleeva, No. 2, 229 (1965).Google Scholar
- 2.V. F. Bystrov, O. A. Yuzhakova, and R. G. Kostyanovskii, DAN SSSR,147, 843 (1962).Google Scholar
- 3.R. W. Taft, E. Price, I. R. Fox, I. C. Lewis, K. K. Andersen, and G. T. Davis, J. Amer. Chem. Soc.,85, 709, 3146 (1963).Google Scholar
- 4.R. W. Taft and I. C. Lenic, J. Amer. Chem. Soc.,80, 2436 (1958); R. W. Taft, S. Ehrenson, I. C. Lewis, and R. E. Glick, J. Amer. Chem. Soc.,81, 5352 (1959).Google Scholar
- 5.R. Daudel, R. Lefebvre, and C. Moser, Quantum Chemistry, Methods and Applications, Inters. Publ. New York (1959).Google Scholar
- 6.G. S. Kolesnikov, Syntheses of Vinyl Derivatives of Aromatic and Heterocyclic Compounds [in Russian], Izd. AN SSSR, Moscow (1960).Google Scholar
- 7.C. D. Cook and S. S. Danyluk, Tetrahedron,19, N1, 177 (1963).Google Scholar
- 8.R. Ya. Levina, P. A. Gembitskii, L. P. Guseva, and P. K. Agasyan, Zh. obshch. khimii,34, 146 (1964); Yu. S. Shabarov, V. K. Potapov, and R. Ya. Levina, Zh. obshch. khimii,34, 2832 (1964).Google Scholar
- 9.G. Vavon and P. Mottez, Compt. rend.,218, 558 (1944).Google Scholar
- 10.D. E. Pearson, J. Organ. Chem.,23, 1412 (1958).Google Scholar
- 11.G. Wittig and K. Schwarzenbach, Liebigs Ann. Chem.,650, 1 (1961).Google Scholar
- 12.H. H. Jaffe, Chem. Rev.,53, 191 (1953).Google Scholar
- 13.V. A. Pal'm, Uspekhi khimii,30, 1069 (1961).Google Scholar