Tertiary alkanamines

Some of the most important reactions of amines are brought about by nitrous acid (HONO). The character of the products depends very much on whether the amine is primary, secondary, or tertiary. In fact, nitrous acid is a useful reagent to determine whether a particular amine is primary, secondary, or tertiary. With primary amines nitrous acid results in evolution of nitrogen gas with secondary amines insoluble yellow liquids or solid 7V-nitroso compounds, R2N—N=0, separate tertiary alkanamines dissolve in and react with nitrous acid solutions without evolution of nitrogen, usually to give complex products ... 

The base strengths of simple alkanamines usually are around Kb = 10-4 (Ka = 10-10) in water solution, and vary within perhaps a factor of 10 from ammonia to primary, secondary, and tertiary amines, as can be seen from the data in Table 23-1. Cyclohexanamine has about the same base strength as methanamine, whereas the effect on the basic nitrogen of being in a saturated ring, as in azacyclohexane, increases the base strength somewhat. 

Much like primary amines, secondary and tertiary amines can also be named as alkyl amines or as alkanamines. Once again, the complexity of the alkyl groups typically determines which... 

The aromatic amines, or anilines, are called benzenamines (Section 15-1). For secondary and tertiary anunes, the largest alkyl substituent on nitrogen is chosen as the alkanamine stem, and the other groups are named by using the letter N-, followed by the name of the additional substituent(s). 

Amines react with nitrous acid, through nucleophilic attack on the nitrosyl cation, NO. The product depends very much on whether the reactant is an alkanamine or a benzenamine (aniline) and on whether it is primary, secondary, or tertiary. This section deals with alkanamines aromatic amines will be considered in the next chapter. 

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