By Muriel Tomlinson
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Extra resources for An Introduction to the Chemistry of Benzenoid Compounds
A true compound, capable in principle of isolation, it lies in an energy trough at W: transition states, on the other hand, exist at energy maxima, ΤΛ and T29 and do not represent even potentially isolable species. Not much is known about the precise geometry or energy of the transition states so the graph is merely to show the various energy troughs and peaks and has no quantitative significance. Figure 5 represents a substitution in which the slower, and therefore ratecontrolling, stage of the process is the formation of the intermediate 25 BENZENE A N D ITS HOMOLOGUES Potential energy qft+XY Reactants Products Reaction co-ordinate FIG.
2 moments are called positive when the positive end of the dipole is remote from the hydrocarbon residue : those in the opposite direction are called negative (Sutton, 1955). -substitutions predominate. DISUBSTITUTION IN BENZENOID COMPOUNDS 37 When the group attracts the π-electrons from the benzene ring (mArX -raAlkX) is negative and substitution occurs mainly in the ra-position. FURTHER CONSIDERATION OF THE MECHANISM OF AROMATIC SUBSTITUTION Substitution into a benzene nucleus which already carries a sub stituent must proceed by a path related to that already described for benzene itself, but the presence of the substituent will clearly affect the stability of the transition states and the Wheland intermediate, and from what has been said above, it is obvious that the effect of a substituent will not be the same at all positions on the nucleus.
An Introduction to the Chemistry of Benzenoid Compounds by Muriel Tomlinson
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