Polynitro aromatic compounds in analytical chemistry I: reaction with ouabain and digitoxin.
By the use of NMR spectroscopy, the highly colored reaction products formed by ouabain or digitoxin in with 1,3,5-trinitrobenzene or 2,4,6-trinitroanisole in the presence of alkali (as used for the determination of these glycosides) are shown to be Meisenheimer complexes. The complexes are produced by attachment of a carbon of the butenolide ring to an aromatic carbon of the nitro compound with formation of a charge-delocalized cyclohexadienate anion.
D000840:Anisoles; D055598:Chemical Phenomena; D002621:Chemistry; D003116:Color; D004074:Digitoxin; D009682:Magnetic Resonance Spectroscopy; D009574:Nitro Compounds; D010042:Ouabain; D014301:Trinitrobenzenes
D000840:Anisoles; D009574:Nitro Compounds; D014301:Trinitrobenzenes; D010042:Ouabain; D004074:Digitoxin