Цвиттерионы: Структура, Свойства и Примеры

Molecule containing an equal number of positive and negative functional groups
In chemistry, a zwitterion ('/t//s//v//ɪ//t//ə/,/r//aɪ//ə//n/ TSVITəryeən; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively and negatively charged functional groups. With amino acids, for example, in solution a chemical equilibrium will be established between the "parent" molecule and the zwitterion. Betaines are zwitterions that cannot isomerize to an all neutral form, such as when the positive charge is located on a quaternary ammonium group. Similarly, a molecule containing a phosphonium group and a carboxylate group cannot isomerize.

Sulfamic acid crystallizes in the zwitterion form. In crystals of anthranilic acid there are two molecules in the unit cell. One molecule is in the zwitterion form, the other is not. In the solid state, H4EDTA is a zwitterion with two protons having been transferred from carboxylic acid groups to the nitrogen atoms. In psilocybin, the proton on the dimethyl amino group is labile and may jump to the phosphate group to form a compound which is not a zwitterion.

Insight to the equilibrium in solution may be gained from the results of theoretical calculations. For example, pyridoxal phosphate, a form of vitamin B6, in aqueous solution is predicted to have an equilibrium favoring a tautomeric form in which a proton is transferred from the phenolic OH group to the nitrogen atom. Because tautomers are different compounds, they sometimes have different enough structures that they can be detected independently in their mixture. This allows experimental analysis of the equilibrium.

The compound trimethylglycine, which was isolated from sugar beet, was named as "betaine". Later, other compounds were discovered that contain the same structural motif, a quaternary nitrogen atom with a carboxylate group attached to it via a –CH2– link. At the present time, all compounds whose structure includes this motif are known as betaines. Betaines do not isomerize because the chemical groups attached to the nitrogen atom are not labile. These compounds may be classed as permanent zwitterions, as isomerisation to a molecule with no electrical charges does not occur, or is very slow. Other examples of permanent zwitterions include phosphatidylcholines, which also contain a quaternary nitrogen atom, but with a negatively charged phosphate group in place of a carboxylate group; sulfobetaines, which contain a quaternary nitrogen atom and a negatively charged sulfonate group; and pulmonary surfactants such as dipalmitoylphosphatidylcholine. Lauramidopropyl betaine is the major component of cocamidopropyl betaine.

Strongly polarized conjugated compounds (conjugated zwitterions) are typically very reactive, share diradical character, activate strong bonds and small molecules, and serve as transient intermediates in catalysis. Donor acceptor entities are of vast use in photochemistry (photoinduced electron transfer), organic electronics, switching and sensing.