Electrophilic and Electrodotic Reagents

The Resemblance of Oxidation-Reduction to Acid-Base Reactions. . 69 

The experimental relationship between acids and oxidizing agents is a close one. In fact, as has been pointed out in Chapter 3, the typicaF effect of an acid solution on metals is due to the oxidizing action of the solvent cation for example  

The acidic cation of the solvent in this particular type of reaction is behaving not as an acid but as an oxidizing agent. The action of basic anions upon non-metals (already referred to) is comparable. Hydroxyl ions in water, and amide ions in liquid ammonia, reduce active non-metals, for example  

These experimental data show the close relationship between acids and oxidizing agents on the one hand and bases and reducing agents on the other, but occasionally a comparison has been attempted which, at first glance, seems to lead to an opposite conclusion. 

A formal analogy is worked out as follows A reducing agent is an electron donor. An acid is a proton donor. An acid, therefore, 

---

A few reagents are listed in Table 1 according to some manifestations of their electrophilic and electrodotic tendencies. The most active oxidizing agent, fluorine, is placed at the top of the... 

We also note briefly an instructive four-way classification [2] of various reagents as primarily electrophilic (acids and oxidants) and electrodotic (bases and reductants). Typical are Mn04 (oxidant) BF3 (acid) Ag (both oxidant and acid) Cs (reductant) F (base) S (both reductant and base) and H2O (all four). 

When two triarylmethyl molecules associate, each one is acting simultaneously as an electrophilic and as an electrodotic reagent to form a covalent bond ... 

---