More About the Acid-Base Properties of Amines

Saturated heterocycles with oxygen and sulfur heteroatoms are named similarly. The prefix for oxygen is oxa and the prefix for sulfur is thia. [Pg.991]

2 MORE ABOUT THE ACID-BASE PROPERTIES OF AMINES [Pg.991]

Amines are the most common organic bases. We have seen that ammonium ions have values of about 10 (Section 2.3) and anilinium ions have p a values of about 5 (Sections 8.15 and 19.16). And we have seen that the greater acidity of anilinium ions compared with ammonium ions is due to the greater stability of the conjugate bases of the anilinium ions as a result of electron delocalization. Amines have very high p a values. For example, the pA a of methylamine is 40. [Pg.991]

Saturated amine heterocycles containing five or more atoms have physical and chemical properties like those of acyclic amines. For example, pyrrolidine, piperidine, and morpholine are typical secondary amines, and iV-methylp5Trolidine and quinucUdine are typical tertiary amines. The conjugate acids of these amines have the p a values expected for ammonium ions. [Pg.991]

Atropine is a naturally occurring heteocycUc compound found in Jimson weed and nightshade Atropa belladonna). The Tf isomer is the one nature synthesizes, hut it racemizes during isolation. Atropine has a variety of medicinal usages, thus landing it on the hst of dmgs the World Health Organization deems needed for basic health care. [Pg.992]

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