19.1
Amine: Einführung
Amine sind organische Derivate von Ammoniak. Sie werden gebildet, indem ein oder mehrere Ammoniakprotonen durch Alkyl- oder Arylgruppen ersetzt werden…
Amine sind organische Derivate einer anorganischen Verbindung – Ammoniak, wobei ein oder mehrere Wasserstoffatome durch Alkyl- oder Arylgruppen ersetzt werden.
Sie werden als primäre, sekundäre oder tertiäre Amine klassifiziert, basierend auf dem Substitutionsgrad am Stickstoffatom.
Ist das Stickstoffatom an einen oder mehrere Alkylkohlenstoffe gebunden, wird das Amin als aliphatisches Amin eingestuft. Ist einer der gebundenen Kohlenstoffe Teil einer Arylgruppe, handelt es sich bei dem Amin um ein aromatisches Amin.
Amine, bei denen Stickstoff Teil einer Ringstruktur ist, werden als heterozyklische Amine bezeichnet. Wenn der Ring aromatisch ist, werden solche Amine als heterozyklische aromatische Amine klassifiziert.
Das Stickstoffatom kann auch vier Organylgruppen tragen. Solche Amine tragen eine formal positive Ladung und liegen als quartäre Ammoniumsalze vor.
Amine kommen in der Natur weit verbreitet vor und haben verschiedene physiologische Wirkungen. Zum Beispiel ist Kokain, ein tertiäres Amin, das aus Kokablättern gewonnen wird, ein Stimulans des Zentralnervensystems.
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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.