On structural formulas of basic fuchsin and aldehyde-Schiff reaction products. 1975

H Puchtler, and S N Meloan, and B R Brewton

A variety of structural formulas has been suggested for the basic fuchsin moiety of aldehyde-Schiff reaction products. It was therefore deemed of interest to review the development of these different concepts of dye structure. Formulation of basic fuchsin as an ammonium salt preceded the quinonoid theory; however, chemists could not find such salts. The quinoid theory also could not be reconciled with chemical observations and spectroscopic data. In the 1920's the quinonoid formulas were superseded by benzenoid formulas with a positive charge at the central carbon atom. Using the resonance theory, basic fuchsin is often written with an apparently pentavalent nitrogen atom at a quinonoid ring. But such limiting structures do not exist in reality; the structure of the resonance hybrid is intermediate between the various contributing structures. The carbonium formula appears preferable to other limiting structures because it would remove temptations to endow basic fuchsin with a quinonoid ring, an imino or an ammonium group. Some formulas of aldehyde-Schiff reaction products carry two positive charges. But divalent basic fuchsin is very unstable. The divalent form of its derivatives formaldehyde- Schiff's reagent, aldehyde-fuchsin, and Crystal Violet is deep green; with decreasing H-ion concentration the divalent green compounds revert to the red or violet monovalent substance. It appears therefore highly unlikely that divalent basic fuchsin exists in PAS reaction products in washed and dehydrated sections.

UI MeSH Term Description Entries
D002625 Chemistry, Organic The study of the structure, preparation, properties, and reactions of carbon compounds. (McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed) Organic Chemistry
D000447 Aldehydes Organic compounds containing a carbonyl group in the form -CHO. Aldehyde
D012394 Rosaniline Dyes Compounds that contain the triphenylmethane aniline structure found in rosaniline. Many of them have a characteristic magenta color and are used as COLORING AGENTS. Fuchsins,Magentas,Fuchsin,Triphenylmethane Aniline Compounds,Aniline Compounds, Triphenylmethane,Compounds, Triphenylmethane Aniline,Dyes, Rosaniline
D012545 Schiff Bases Condensation products of aromatic amines and aldehydes forming azomethines substituted on the N atom, containing the general formula R-N:CHR. (From Grant & Hackh's Chemical Dictionary, 5th ed) Schiff Base,Base, Schiff,Bases, Schiff
D049672 History, 19th Century Time period from 1801 through 1900 of the common era. 19th Century History,19th Cent. History (Medicine),19th Cent. History of Medicine,19th Cent. Medicine,Historical Events, 19th Century,History of Medicine, 19th Cent.,History, Nineteenth Century,Medical History, 19th Cent.,Medicine, 19th Cent.,19th Cent. Histories (Medicine),19th Century Histories,Cent. Histories, 19th (Medicine),Cent. History, 19th (Medicine),Century Histories, 19th,Century Histories, Nineteenth,Century History, 19th,Century History, Nineteenth,Histories, 19th Cent. (Medicine),Histories, 19th Century,Histories, Nineteenth Century,History, 19th Cent. (Medicine),Nineteenth Century Histories,Nineteenth Century History
D049673 History, 20th Century Time period from 1901 through 2000 of the common era. 20th Century History,20th Cent. History (Medicine),20th Cent. History of Medicine,20th Cent. Medicine,Historical Events, 20th Century,History of Medicine, 20th Cent.,History, Twentieth Century,Medical History, 20th Cent.,Medicine, 20th Cent.,20th Cent. Histories (Medicine),20th Century Histories,Cent. Histories, 20th (Medicine),Cent. History, 20th (Medicine),Century Histories, 20th,Century Histories, Twentieth,Century History, 20th,Century History, Twentieth,Histories, 20th Cent. (Medicine),Histories, 20th Century,Histories, Twentieth Century,History, 20th Cent. (Medicine),Twentieth Century Histories,Twentieth Century History

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