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Related Concept Videos

Structure of Amines01:19

Structure of Amines

3.4K
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 is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
3.4K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.8K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.8K
Preparation of Amides01:29

Preparation of Amides

4.3K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
4.3K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.8K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
4.8K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

9.8K
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...
9.8K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.5K
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 situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.5K

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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Quantifying transient interactions between amide groups and the guanidinium cation.

V Balos1, M Bonn1, J Hunger1

  • 1Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany. hunger@mpip-mainz.mpg.de.

Physical Chemistry Chemical Physics : PCCP
|October 14, 2015
PubMed
Summary
This summary is machine-generated.

Guanidinium cations interact directly but weakly with protein amide groups. This interaction is transient, unlike stronger binding seen with other charged molecules.

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Facile Preparation of 4-Substituted Quinazoline Derivatives

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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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Area of Science:

  • Biochemistry
  • Chemical Physics

Background:

  • Proteins are essential biological macromolecules.
  • Protein structure is stabilized by various chemical interactions.
  • Guanidinium is a known protein denaturant.

Purpose of the Study:

  • Investigate the interaction between guanidinium cations and amide groups.
  • Characterize the binding strength and transient nature of this interaction.

Main Methods:

  • Computational simulations or spectroscopic analysis (details not provided in abstract).

Main Results:

  • Direct contact observed between guanidinium and approximately two amide groups.
  • The guanidinium-amide interaction is transient.
  • Interaction strength is weaker compared to other high charge-density cations.

Conclusions:

  • Guanidinium's denaturing effect may involve weak, transient interactions with protein backbone amide groups.
  • Understanding these interactions is crucial for protein chemistry and drug design.