Processes Erasing pH Memory

A similar process can occur if the acid or base can be extracted into the bulk phase of the reaction mixture (e.g. octanoic acid or triethylamine in an organic solvent). 

Other counter-ions may be exchanged with the bulk non-polar phase, provided something is able to solubilize them there. This will usually be in the form of an ion-pair with a species better solvated by the medium. For example, an acid with a large hydrophobic group may form a Na+ salt with sufficient solubility in the bulk medium. The protonated acid will carry H+ to and from the enzyme in exchange, to maintain electroneutrality. A similar process with a hydrophobic amine, for example, can transfer H+ and Cl-. Solubilization of the small ion may be aided by complexa-tion, for example of Na+ by a crown ether. The exchanges can be written as  

Protein-NH3+.Cl + R3N (bulk phase) Protein-NH2 + R3NH+.C1- (bulk phase) (5) 

Acidic or basic species in the bulk phase may protonate or deprotonate the enzyme, becoming the necessary counter-ions in the process. So we might have equilibria such as  

Protein-COOH + CH3NH2 (bulk phase) Protein-COO .+NH3CH3 (6) 

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