Orthoeffect and steric inhibition of resonance: basicities of methyl-substituted acetophenones

2003 ◽  
Vol 16 (10) ◽  
pp. 721-725 ◽  
Author(s):  
Eva Otyepková ◽  
Tat'jana Nevěčná ◽  
Jiří Kulhánek ◽  
Otto Exner
2020 ◽  
Vol 23 (23) ◽  
pp. 2598-2613
Author(s):  
Boris A. Zaitsev

: A retrospective view of exaltation of refraction observed for many unsaturated and aromatic compounds demonstrates that this physical phenomenon is undeservedly considered only as a qualitative measure of conjugation. This mini-review discusses numerous papers by the author that have been published earlier in inaccessible periodicals and collections of scientific papers. Using a great number of illustrations, the author shows that this parameter can be successfully used for quantitative estimate of resonance effects in organic and polymer chemistry. The methods for derivation of strictly additive atomic and group refraction constants are described; these constants were subsequently used as a tool that allowed quantitative estimation of resonance effects in mono-, di-, tri- and polyalkylbenzenes, alkylnaphthalenes, some alkyl derivatives of unsaturated hydrocarbons. These effects cause strictly fixed increase in refraction of carbon atoms in different structural modifications (graphene, fullerene, diamond) and in polycyclic aromatic hydrocarbons. The relevant results regarding quantitative estimation of degree of steric inhibition of resonance in sterically hindered ortho-dialkylbenzenes, 1,2,3- trialkyl-, 1,2,3,4-tetraalkyl-, and 1,2,3,4,5-polyalkylbenzenes accumulated by the author are summarized.


2003 ◽  
Vol 2003 (5) ◽  
pp. 303-304 ◽  
Author(s):  
Inmaculada C. Rodriguez Medina ◽  
James R. Hanson

The orientation of dinitration of the dimethylacetanilides has been examined by 1H NMR methods and a possible enhancement of the hyperconjugative influence of a methyl group has been considered as an additional factor augmenting the effect of the steric inhibition of resonance on the orientation of substitution.


1949 ◽  
Vol 27b (5) ◽  
pp. 437-461 ◽  
Author(s):  
Y. Hirshberg ◽  
R. Norman Jones

The ultraviolet absorption spectra of a variety of naphthalene compounds containing phenyl and carboxy substituents are described. The majority of the compounds contain either the naphthalene-1,2-dicarboxylic acid anhydride or the naphthalene-2,3-dicarboxylic acid anhydride ring systems. It is shown that in ethanolic solution the spectra of these anhydrides change over a period of a few hours. The spectra of the anhydrides in n-heptane or dioxane solution do not change on standing. The effects of the various substituents are discussed in terms of steric inhibition of resonance and of antagonistic and reinforcing actions of the substituents, dependent on the position of substitution. The significance of these data are considered in relation to the general problem of the interpretation of the ultraviolet absorption spectra of complex molecules.


Tetrahedron ◽  
1973 ◽  
Vol 29 (1) ◽  
pp. 199-204 ◽  
Author(s):  
A. Balsamo ◽  
P. Crotti ◽  
B. Macchia ◽  
F. Macchia

1974 ◽  
Vol 4 (1) ◽  
pp. 90-92 ◽  
Author(s):  
S. Pignataro ◽  
R. Di Marino ◽  
G. Distefano

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