Naphthylamines Hydrated

The alteration of nucleophilic reactivity by the intervention of covalent hydration and analogous nucleophilic additions needs to be borne in mind for many polyazanaphthalenes. Covalent hydration has been observed in several bicyclic azines besides pteridine and quinazoline (Section IV, B) and is related to nucleophilic substitution in activation and in proceeding through the same first stage as 8 Ar2 reactions. The Bucherer interconversion of naphthols and naphthylamines involves exchange of oxygen and nitrogen substituents in a covalent adduct produced by bisulfite ion. ... 

Hydrated Naphthylamines.— We have referred to the hydrated naphthylamines in our discussion of the constitution of naphthalene (p. 772). The tetra-hydro products are of two kinds (i) Those termed aromatic in which the hydrogen is added to the benzene nucleus which does not contain the amino group and which possess the characters of aromatic amines. (2) Those termed alicyclic in which the hydrogen is added to the benzene nucleus which does contain the amino group and which possess the characters of aliphatic amines. Now while the alpha- and g/a-naphthylamines each yield both kinds of tetra-hydro products if subjected to proper treatment yet by the same treatment, viz., with sodium amalgam in amyl alcohol, the atpha-naphthylamine yields an aromatic tetra-hydro compound while the i>e/o-naphthylamine yields mostly an alicyclic compound. 

FD C Yellow No. 6 Glucose Grape skin extract Iron oxide black Iron (III) oxide hydrated Iron oxide yellow monohydrate Magnesium carbonate Magnesium stearate Malt extract 1-(Phenylazo)-2-naphthylamine Pyrogallol Riboflavin Talc Zinc chloride colorant, plastics... 

Proton-induced quenching often plays an important role in acid-base equilibrium in the excited state of aromatic molecules as described above. For the proton-induced quenching mechanism of naphthylamines, a complex in which a proton is shared between excited 2-naphthylamine and one water molecule [43] or a hydrated naphthylammonium cation in the ground state [44] was assumed as an intermediate... 

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