Muriel Tomlinson's An Introduction to the Chemistry of Benzenoid Compounds PDF

By Muriel Tomlinson

ISBN-10: 0080156592

ISBN-13: 9780080156590

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Example text

This is true of nitration in which it has been shown that replacement of tritium does not proceed more slowly than replacement of hydrogen. With reactions like sulphonation where replacement of deuterium or tritium is slower than replace­ ment of hydrogen the second energy barrier must be close to, or higher than, the first and the rate-controlling stage is the removal of the proton (Fig. 6). If ττ-complexes form a part of the reaction they must appear in the energy profile (Fig. 7). FIG. 6. FIG.

Because the precise geometry and the distribution of charge between the entering group and the nucleus are unknown for the transition state, 38 INTRODUCTION TO THE CHEMISTRY OF BENZENOID COMPOUNDS H /«+ δ+ i I we are forced to try to decide whether the ground-state of the mole­ cule (S) or the stability of the intermediate {W) provides a closer approximation to the conditions at Tl9 and which gives the better understanding of what actually occurs. Thus there are two possible approaches to the problem, the isolated molecule method which relates to the ground-state and the localisation energy method which considers the Wheland intermediate.

Cl2 > Cl· + Cl· The reactions can also be effected by using boiling benzene. e. hexachloro- and hexabromocyclohexanes, and are mixtures of geometrical isomers in which the halogen atoms are arranged above and below the plane of the ring: here the ring is, as in cyclohexane, buckled so that normal valency angles are maintained (the carbon atoms are now sp* hybridised). Perhaps the most interesting isomer is the one which has the con­ figuration (15) which, under the name gammexane, has found use as an insecticide.

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An Introduction to the Chemistry of Benzenoid Compounds by Muriel Tomlinson


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