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54, 713. BAILEY and CASE (1958) A new series of complexing reagents for aromatic hydrocarbons, Tetrahedron, 3,113. C. , 81,100. HASSELL and ROMMING (1962) Charge transfer spectra bonds in solids, Quart, Rev. XVI, 11. C. Lecture Series No. 5. MILLAR and SPRINGALL (1966) Sidgwick's Organic Chemistry of Nitrogen, Clarendon Press, pp. 397, 483. NORMAN, Principles of Organic Synthesis, Methuen, p. 553. PAUSON (1967) Organometallic Chemistry, Arnold.

There is no evidence that alkyl-groups actually repel electrons; it may be that hydrogen attracts electrons more than alkyls do. 34 INTRODUCTION TO THE CHEMISTRY OF BENZENOID COMPOUNDS (1) (2) Hydroxyl and amino-groups, because of the higher nuclear charge of oxygen and nitrogen compared to carbon, must have —I effects. Robinson called the other way in which a substituent reacts electronically with a nucleus an electromeric effect t and represented it by formulae such as (3) (Ingold later introduced the term mesomeric effect for this).

P. p. p. —6-5°, gave three isomerie nitro-com­ pounds. p. 6-7 Br 0 2 N. -6-5° Once one or two cases are established it is comparatively easy to relate others to them by means of the many interconversions which can readily be carried out. For example DISUBSTITUTION IN BENZENOID COMPOUNDS 31 — Cl / — N02 s — Br — — MgBr · COOH - — N H 2 — - — OH I ^ —CN—*-—COOH— CH3 I and orientation problems were quickly solved for all common substitutents. FURTHER SUBSTITUTION INTO SUBSTITUTED BENZENOID COMPOUNDS It soon became clear that the product of a benzene disubstitution reaction is generally either (a) mainly a mixture of ortho- and paraisomers, or (b) chiefly the meta-compound.

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