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在水中和氨酸之间的直接C-sp3结合形成

  • 0Department of Chemistry, Stanford University, Stanford, California 94305, United States.

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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO<sub data-lazy-src=

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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 solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

Figure 1. The mechanism of the diazotization reaction of primary amines.
As illustrated in Figure 1, in the...

Aldehydes and Ketones with Amines: Imine Formation Mechanism 01:23

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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...

Electrophilic Aromatic Substitution: Nitration of Benzene 01:20

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

Sulfuric acid is stronger and protonates the nitric acid on the hydroxyl group, followed by loss of water molecule, generating the nitronium ion.

The nitronium ion acts as an electrophile that reacts with...

NMR Spectroscopy Of Amines 01:19

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In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is...

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Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.

The acid-catalyzed mechanism involves the protonation of the nitrogen atom to make the carbon atom more susceptible to nucleophilic attack. The second step involves the nucleophilic attack by water on the nitrile carbon atom. Subsequently, deprotonation of the oxygen atom gives a tautomeric form of an amide, and protonation of the nitrogen forms...