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Chapter 19

Amines

Amines : Introduction
Amines : Introduction
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 ...
Nomenclature des amines primaires
Nomenclature des amines primaires
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), ...
Nomenclature des amines secondaires et tertiaires
Nomenclature des amines secondaires et tertiaires
The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary ...
Nomenclature des amines aryliques et hétérocycliques
Nomenclature des amines aryliques et hétérocycliques
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is ...
Structure des amines
Structure des amines
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 ...
Propriétés physiques des amines
Propriétés physiques des amines
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, ...
Basicité des amines aliphatiques
Basicité des amines aliphatiques
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 ...
Basicité des amines aromatiques
Basicité des amines aromatiques
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 ...
Basicité des amines aromatiques hétérocycliques
Basicité des amines aromatiques hétérocycliques
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine ...
Spectroscopie RMN des amines
Spectroscopie RMN des amines
In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between ...
Spectrométrie de masse des amines
Spectrométrie de masse des amines
In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule: a ...
Préparation des amines : alkylation de l’ammoniac et des amines
Préparation des amines : alkylation de l’ammoniac et des amines
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 ...
Préparation de 1° amines : synthèse de l’azoture
Préparation de 1° amines : synthèse de l’azoture
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide ...
Préparation de 1° Amines : Synthèse de Gabriel
Préparation de 1° Amines : Synthèse de Gabriel
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred ...
Préparation des amines : réduction des oximes et des composés nitrés
Préparation des amines : réduction des oximes et des composés nitrés
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and ...
Préparation des amines : réduction des amides et des nitriles
Préparation des amines : réduction des amides et des nitriles
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an ...
Préparation des amines : amination réductrice d’aldéhydes et de cétones
Préparation des amines : amination réductrice d’aldéhydes et de cétones
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, ...
Préparation de 1° Amines : réarrangement de Hofmann et Curtius Vue d’ensemble
Préparation de 1° Amines : réarrangement de Hofmann et Curtius Vue d’ensemble
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 ...
Préparation de 1° amines : mécanisme de réarrangement de Hofmann et Curtius
Préparation de 1° amines : mécanisme de réarrangement de Hofmann et Curtius
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl ...
Amines à amides : acylation des amines
Amines à amides : acylation des amines
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction ...
Des amines aux alcènes : l’élimination de Hofmann
Des amines aux alcènes : l’élimination de Hofmann
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. ...
De l’amine à l’alcène : l’élimination de la face
De l’amine à l’alcène : l’élimination de la face
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1. ...
1° Amines en sels de diazonium ou d’aryldiazonium : diazotisation au NaNO<sub>2</sub> Vue d’ensemble
1° Amines en sels de diazonium ou d’aryldiazonium : diazotisation au NaNO2 Vue d’ensemble
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° Des amines aux sels de diazonium ou d’aryldiazonium : Mécanisme de diazotisation avec NaNO<sub>2</sub>
1° Des amines aux sels de diazonium ou d’aryldiazonium : Mécanisme de diazotisation avec NaNO2
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° Amines en N-nitrosamines : réaction avec le NaNO<sub>2</sub> <em></em>
2° Amines en N-nitrosamines : réaction avec le 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 ...
Substitution du groupe diazonium par des halogènes et du cyanure : réactions de Sandmeyer et de Schiemann
Substitution du groupe diazonium par des halogènes et du cyanure : réactions de Sandmeyer et de Schiemann
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. ...
Substitution du groupe diazonium : –OH et –H
Substitution du groupe diazonium : –OH et –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 ...
Sels d’aryldiazonium aux colorants azoïques : couplage diazo
Sels d’aryldiazonium aux colorants azoïques : couplage diazo
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of ...
De l’amine au sulfamide : le test de Hinsberg
De l’amine au sulfamide : le test de Hinsberg
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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