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Related Concept Videos

Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

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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 along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Preparation of Amides01:29

Preparation of Amides

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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...
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
7.8K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

10.2K
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...
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Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

5.0K
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...
5.0K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.9K
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...
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Epoxy-terminated self-assembled monolayers containing internal urea or amide groups.

Michaël A Ramin1, Gwénaëlle Le Bourdon, Karine Heuzé

  • 1ISM, UMR 5255 CNRS, Université de Bordeaux , 351 cours de la Liberation CS 10004, 33 405 Talence, France.

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Summary

New coupling agents with internal amide/urea groups and epoxy terminals form self-assembled monolayers (SAMs). These SAMs offer higher accessible epoxide density compared to long-chain glycidyl SAMs, enhancing surface reactivity.

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Area of Science:

  • Materials Science
  • Surface Chemistry
  • Organic Chemistry

Background:

  • Self-assembled monolayers (SAMs) are crucial for surface functionalization.
  • Epoxy-terminated SAMs are valuable for subsequent chemical modifications.
  • Designing SAMs with enhanced reactivity and controlled molecular assembly is an ongoing challenge.

Purpose of the Study:

  • To synthesize novel coupling agents with internal amide or urea groups, an epoxy-terminal group, and a trimethoxysilyl-anchoring group.
  • To investigate the structural characteristics and molecular assembly of the resulting SAMs.
  • To evaluate the accessibility and reactivity of the epoxy groups in these novel SAMs.

Main Methods:

  • Synthesis of new coupling agents containing amide/urea and epoxy functionalities.
  • Formation of self-assembled monolayers (SAMs) on surfaces.
  • Structural characterization using polarization modulation infrared reflection adsorption spectroscopy (PM-IRRAS).
  • Assessment of epoxy group reactivity via reaction with a fluorescent probe.

Main Results:

  • Successful synthesis of coupling agents with internal amide/urea and epoxy groups.
  • Characterization of SAMs revealing molecular assembly primarily driven by intermolecular hydrogen bonding between amide/urea groups.
  • Steric hindrance from amide/urea groups leads to disorder in alkyl chains due to insufficient van der Waals interactions.
  • Demonstrated higher density of accessible epoxide groups in SAMs with internal urea/amide groups compared to long-chain (C22) glycidyl-terminated SAMs.

Conclusions:

  • Novel coupling agents with internal amide/urea groups enable the formation of functional SAMs.
  • Hydrogen bonding plays a key role in the self-assembly of these SAMs.
  • The designed SAMs exhibit superior accessibility of reactive epoxide groups, offering advantages for surface modification applications.