Chapter 19
Amines
![Amines: Introduction](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12852.jpg)
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the…
![Nomenclature of Primary Amines](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12524.jpg)
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2),…
![Nomenclature of Aryl and Heterocyclic Amines](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12854.jpg)
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is…
![Structure of Amines](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12525.jpg)
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°,…
![Basicity of Aliphatic Amines](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12526.jpg)
Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair…
![Basicity of Aromatic Amines](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12856.jpg)
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…
![NMR Spectroscopy Of Amines](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/13842.jpg)
In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range…
![Mass Spectrometry of Amines](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12857.jpg)
In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen…
![Preparation of 1° Amines: Azide Synthesis](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12530.jpg)
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide…
![Preparation of 1° Amines: Gabriel Synthesis](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12859.jpg)
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most…
![Preparation of Amines: Reduction of Amides and Nitriles](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12860.jpg)
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an…
![Preparation of Amines: Reductive Amination of Aldehydes and Ketones](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12532.jpg)
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture,…
![Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12862.jpg)
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl…
![Amines to Amides: Acylation of Amines](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12534.jpg)
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The…
![Amines to Alkenes: Cope Elimination](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12536.jpg)
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in…
![1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO<sub>2</sub> Overview](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12537.jpg)
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…
![2° Amines to <em>N</em>-Nitrosamines: Reaction with NaNO<sub>2</sub>](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12538.jpg)
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…
![Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12539.jpg)
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile,…
![Quantification of Site-specific Protein Lysine Acetylation and Succinylation Stoichiometry Using Data-independent Acquisition Mass Spectrometry](https://cloudfront.jove.com/files/thumbs/57209_t.png)
Quantification of Site-specific Protein Lysine Acetylation and Succinylation Stoichiometry Using Data-independent Acquisition Mass Spectrometry
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Post-translational modification (PTM) of protein lysine residues by NƐ-acylation induces structural changes that can dynamically regulate…
![Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron](https://cloudfront.jove.com/files/thumbs/60050_t.png)
aza-Michael adducts of tricarbonyl(tropone)iron are synthesized by two different methods. Primary aliphatic amines and cyclic secondary amines…