19.1
Ammine: Introduzione
Le ammine sono derivati organici dell'ammoniaca. Si formano sostituendo uno o più protoni di ammoniaca con gruppi alchilici o arilici. A seconda del n…
Le ammine sono derivati organici di un composto inorganico, l'ammoniaca, con uno o più idrogeni sostituiti da gruppi alchilici o arilici.
Sono classificate come ammine primarie, secondarie o terziarie in base al grado di sostituzione all'atomo di azoto.
Se l'atomo di azoto è legato a uno o più atomi di carbonio alchilici, l'ammina è classificata come ammina alifatica. Se uno dei carboni legati fa parte di un gruppo arilico, l'ammina è un'ammina aromatica.
Le ammine in cui l'azoto fa parte di una struttura ad anello sono chiamate ammine eterocicliche. Se l'anello è aromatico, tali ammine sono classificate come ammine aromatiche eterocicliche.
L'atomo di azoto può anche portare quattro gruppi organilici. Tali ammine hanno una carica positiva formale ed esistono come sali di ammonio quaternario.
Le ammine sono ampiamente presenti in natura e hanno vari effetti fisiologici. Ad esempio, la cocaina, un'ammina terziaria ottenuta dalle foglie di coca, è uno stimolante del sistema nervoso centrale.
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Q1: How are amines classified based on the number of organyl groups attached to nitrogen?
Amines are classified as primary, secondary, or tertiary based on the number of organyl groups bonded to the nitrogen atom. Primary amines have one organyl group, secondary amines have two, and tertiary amines have three. When four organyl groups are present, the nitrogen carries a formal positive charge and exists as a quaternary ammonium salt.
Q2: What is the difference between aliphatic and aromatic amines?
Aliphatic amines have only alkyl groups bonded to the nitrogen atom, while aromatic amines have at least one aryl group bonded to nitrogen. The presence of an aryl group distinguishes aromatic amines from their aliphatic counterparts and affects their chemical properties and reactivity.
Q3: What are heterocyclic amines and how are they further classified?
Heterocyclic amines contain a nitrogen atom as part of a ring structure. They are classified as heterocyclic aliphatic amines when nitrogen is in an aliphatic ring, or heterocyclic aromatic amines when nitrogen is part of an aromatic ring. This ring incorporation significantly influences their chemical behavior and properties.
Q4: What are alkaloids and why are they physiologically important?
Alkaloids are nitrogen-containing molecules of plant origin, most of which are physiologically active in the human body. Examples include coniine, a heterocyclic aliphatic amine that can cause respiratory issues and weakness, and cocaine, a tertiary amine that stimulates the central nervous system when consumed.
Q5: How are amines derived from ammonia?
Amines are organic derivatives of ammonia formed by replacing one or more hydrogen atoms with alkyl or aryl groups. This substitution process creates primary, secondary, or tertiary amines depending on how many hydrogens are replaced. The resulting compounds retain nitrogen as the central heteroatom.
Q6: What happens when a fourth organyl group is bonded to nitrogen in an amine?
When four organyl groups are bonded to nitrogen, the nitrogen atom possesses a formal positive charge. These compounds exist as quaternary ammonium salts rather than neutral amines, fundamentally changing their chemical nature and reactivity compared to primary, secondary, and tertiary amines.
Q7: How can amines be converted into other functional groups?
Amines undergo various transformations in organic synthesis. Primary amines can be converted through preparation of amines reductive amination of aldehydes and ketones, while amines can also be converted to amides through acylation of amines or to other products through elimination and substitution reactions.