Current chemical concepts of acids and bases and their application to anionic (?acid?) and cationic (?basic?) dyes

Abstract

In biomedical studies, dyes are divided into "acid" and "basic" dyes. This classification cannot be reconciled with current chemical definitions of acids and bases. Brönsted-Lowry acids are compounds that can donate protons; bases are proton acceptors. The definition of acids and bases is independent of the electric charge, i.e. acids and bases can be neutral, anionic or cationic. Reactions between acids and bases result in formation of new acid-base pairs. Lewis acids and bases do not depend on a particular element, but are characterized by their electronic configurations. Lewis bases are electron donors; Lewis acids are electron acceptors. This classification is also unrelated to the electric charge. Lewis acids and bases interact by formation of coordinate covalent bonds. In histochemistry and histology, dyes containing -SO3-, -COO- and/or -O- groups are classified as "acid" dyes. However, such compounds are electron pair donors and hence Brönsted-Lowry and Lewis anionic bases. Dyes carrying a positive charge are termed "basic" dyes. Chemically, many cationic dyes are Lewis acids because they can add a base, e.g. OH-, acetate, halides. The hypothesis that transformation of -NH2 into ammonium groups imparts "basic" properties to dyes is untenable; ammonium groups are proton donors and hence acids. Furthermore, conversion of an amino into an ammonium group blocks a lone electron pair and the color of the dye changes drastically, e.g. from violet to green and yellow. It appears therefore highly unlikely that ammonium groups are responsible for binding of cationic ("basic") dyes. In histochemistry, it is usually not of critical importance whether anionic or cationic dyes are chemically acids or bases.(ABSTRACT TRUNCATED AT 250 WORDS)