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Kapitel 19

Amine

Amine: Einführung
Amine: Einführung
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number ...
Nomenklatur der primären Amine
Nomenklatur der primären Amine
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), ...
Nomenklatur der sekundären und tertiären Amine
Nomenklatur der sekundären und tertiären Amine
The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary ...
Nomenklatur der Aryl und heterocyclischen Amine
Nomenklatur der Aryl und heterocyclischen Amine
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is ...
Struktur der Amine
Struktur der Amine
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which ...
Physikalische Eigenschaften von Aminen
Physikalische Eigenschaften von Aminen
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, ...
Basizität der aliphatischen Amine
Basizität der aliphatischen Amine
Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of ...
Basizität der aromatischen Amine
Basizität der aromatischen Amine
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in ...
Basizität von heterocyclischen aromatischen Aminen
Basizität von heterocyclischen aromatischen Aminen
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine ...
NMR Spektroskopie von Aminen
NMR Spektroskopie von Aminen
In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between ...
Massenspektrometrie von Aminen
Massenspektrometrie von Aminen
In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule: a ...
Herstellung von Aminen: Alkylierung von Ammoniak und Aminen
Herstellung von Aminen: Alkylierung von Ammoniak und Aminen
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines ...
Herstellung von 1°-Aminen: Azid-Synthese
Herstellung von 1°-Aminen: Azid-Synthese
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide ...
Herstellung von 1° Aminen: Gabriel-Synthese
Herstellung von 1° Aminen: Gabriel-Synthese
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred ...
Herstellung von Aminen: Reduktion von Oximen und Nitroverbindungen
Herstellung von Aminen: Reduktion von Oximen und Nitroverbindungen
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and ...
Herstellung von Aminen: Reduktion von Amiden und Nitrilen
Herstellung von Aminen: Reduktion von Amiden und Nitrilen
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an ...
Herstellung von Aminen: Reduktive Aminierung von Aldehyden und Ketonen
Herstellung von Aminen: Reduktive Aminierung von Aldehyden und Ketonen
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, ...
Herstellung von 1°-Aminen: Überblick über die Hofmann- und Curtius-Umlagerung
Herstellung von 1°-Aminen: Überblick über die Hofmann- und Curtius-Umlagerung
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary ...
Herstellung von 1°-Aminen: Hofmann- und Curtius-Umlagerungsmechanismen
Herstellung von 1°-Aminen: Hofmann- und Curtius-Umlagerungsmechanismen
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl ...
Amine zu Amiden: Acylierung von Aminen
Amine zu Amiden: Acylierung von Aminen
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction ...
Amine zu Alkenen: Hofmann-Eliminierung
Amine zu Alkenen: Hofmann-Eliminierung
Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. ...
Amine zu Alkenen: Cope-Eliminierung
Amine zu Alkenen: Cope-Eliminierung
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1. ...
1° Amine zu Diazonium- oder Aryldiazoniumsalzen: Diazotierung mit NaNO2 - Übersicht
1° Amine zu Diazonium- oder Aryldiazoniumsalzen: Diazotierung mit NaNO2 - Übersicht
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa ...
1° Amine zu Diazonium- oder Aryldiazoniumsalzen: Diazotierung mit NaNO2 - Mechanismus
1° Amine zu Diazonium- oder Aryldiazoniumsalzen: Diazotierung mit NaNO2 - Mechanismus
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic ...
2° Amine zu N-Nitrosaminen: Reaktion mit NaNO2
2° Amine zu N-Nitrosaminen: Reaktion mit NaNO2
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from ...
Diazoniumgruppen-Substitution mit Halogenen und Cyanid: Sandmeyer und Schiemann-Reaktion
Diazoniumgruppen-Substitution mit Halogenen und Cyanid: Sandmeyer und Schiemann-Reaktion
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. ...
Diazoniumgruppen-Substitution: -OH und -H
Diazoniumgruppen-Substitution: -OH und -H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in ...
Aryldiazoniumsalze zu Azofarbstoffen: Diazokupplung
Aryldiazoniumsalze zu Azofarbstoffen: Diazokupplung
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of ...
Amine zu Sulfonamiden: Der Hinsberg-Test
Amine zu Sulfonamiden: Der Hinsberg-Test
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with ...
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