A Quinonoid zwitterion is a special type of zwitterion

Zwitterion

In chemistry, a zwitterion is a neutral molecule with a positive and a negative electrical charge at different locations within that molecule. Zwitterions are sometimes also called inner salts.-Examples:...

 based on quinone

Quinone

A quinone is a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C– groups with any necessary rearrangement of double bonds," resulting in "a fully conjugated cyclic dione structure."...

 related chemical compound

Chemical compound

A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

s. The benzene

Benzene

Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 derivate 1,3-dihydroxy-4,6-diaminobenzene is easily oxidized by air in water or methanol

Methanol

Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

 to the quinonoid. This compound was first prepared in 1883 and the quinonoid structure first proposed in 1956. In fact in 2002 the compound was found to be more stable and to exist as the zwitterion after a proton

Hydrogen atom

A hydrogen atom is an atom of the chemical element hydrogen. The electrically neutral atom contains a single positively-charged proton and a single negatively-charged electron bound to the nucleus by the Coulomb force...

 transfer. Evidence for this structure is based on NMR spectroscopy

NMR spectroscopy

Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is a research technique that exploits the magnetic properties of certain atomic nuclei to determine physical and chemical properties of atoms or the molecules in which they are contained...

 and x-ray crystallography

X-ray crystallography

X-ray crystallography is a method of determining the arrangement of atoms within a crystal, in which a beam of X-rays strikes a crystal and causes the beam of light to spread into many specific directions. From the angles and intensities of these diffracted beams, a crystallographer can produce a...

. The positive charge is delocalized between the amino groups over 4 bonds involving 6 pi electrons. The negative charge is spread likewise between the oxygen atoms.