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  2. Amide - Wikipedia

    en.wikipedia.org/wiki/Amide

    Compared to amines, amides are very weak bases. While the conjugate acid of an amine has a pK a of about 9.5, the conjugate acid of an amide has a pK a around −0.5. Therefore, compared to amines, amides do not have acid–base properties that are as noticeable in water. This relative lack of basicity is explained by the withdrawing of ...

  3. Aminolysis - Wikipedia

    en.wikipedia.org/wiki/Aminolysis

    Another common example is the reaction of a primary amine or secondary amine with a carboxylic acid or with a carboxylic acid derivative to form an amide. This reaction is widely used, especially in the synthesis of peptides. On the simple addition of an amine to a carboxylic acid, a salt of the organic acid and base is obtained.

  4. Metal amides - Wikipedia

    en.wikipedia.org/wiki/Metal_amides

    The lithium amides are more common and more soluble than the other alkali metal analogs. Potassium amides are prepared by transmetallation of lithium amides with potassium t-butoxide (see also Schlosser base) or by reaction of the amine with potassium, potassium hydride, n-butylpotassium, or benzylpotassium. [2]

  5. Amine - Wikipedia

    en.wikipedia.org/wiki/Amine

    Amine. In chemistry, amines (/ ə ˈ m iː n, ˈ æ m iː n /, [1] [2] UK also / ˈ eɪ m iː n / [3]) are compounds and functional groups that contain a basic nitrogen atom with a lone pair.Formally, amines are derivatives of ammonia (NH 3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group [4] (these may respectively be called alkylamines ...

  6. Mannich reaction - Wikipedia

    en.wikipedia.org/wiki/Mannich_reaction

    Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich. [2] [3] Scheme 1 – Ammonia or an amine reacts with formaldehyde and an alpha acidic proton of a carbonyl compound to a beta amino carbonyl compound.

  7. Transamidation - Wikipedia

    en.wikipedia.org/wiki/Transamidation

    Transamidation is a chemical reaction in which an amide reacts with an amine to generate a new amide: RC(O)NR' 2 + HNR" 2 → RC(O)NR" 2 + HNR' 2. The reaction is typically very slow, but it can be accelerated with Lewis acid [1] and organometallic catalysts. [2] Primary amides (RC(O)NH 2) are more amenable to this reaction.

  8. Hofmann rearrangement - Wikipedia

    en.wikipedia.org/wiki/Hofmann_rearrangement

    The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. [1] [2] [3] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.

  9. Lactam - Wikipedia

    en.wikipedia.org/wiki/Lactam

    For example, Fmoc-Dab(Mtt)-OH, although its side-chain amine is sterically protected by extremely bulky 4-Methyltrityl (Mtt) group, the amine can still intramolecularly couple with the carboxylic acid to form a γ-lactam. This reaction almost finished within 5 minutes with many coupling reagents (e.g. HATU and PyAOP). [1]