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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

4.0K
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...
4.0K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.5K
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...
4.5K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.5K
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...
3.5K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.3K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
4.3K
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

6.3K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
6.3K
¹³C NMR: ¹H–¹³C Decoupling01:04

¹³C NMR: ¹H–¹³C Decoupling

1.8K
The probability of having two carbon-13 atoms next to each other is negligible because of the low natural abundance of carbon-13. Consequently, peak splitting due to carbon-carbon spin-spin coupling is not observed in spectra. However, protons up to three sigma bonds away split the carbon signal according to the n+1 rule, resulting in complicated spectra.
A broadband decoupling technique is used to simplify these complex, sometimes overlapping, signals. Broadband decoupling relies on a...
1.8K

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Microstructure of amide-functionalized polyethylenes determined by NMR relaxometry.

Shira Haber1, Nicodemo R Ciccia2,3, Zhengxing Peng1,4

  • 1Materials Sciences Division, Lawrence Berkeley National Laboratory 1 Cyclotron Road Berkeley CA 94720 USA shira.haber@biu.ac.il reimer@berkeley.edu.

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Amide functional groups in polyethylene were studied using nuclear magnetic resonance (NMR) techniques. These amidyl groups were found to localize in the rigid amorphous fraction, influencing material microstructure and properties.

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Area of Science:

  • Polymer Science
  • Materials Science
  • Organic Chemistry

Background:

  • Amidation of polyethylenes introduces amide groups, enhancing material properties.
  • The impact of these functional groups on polymer microstructure remains largely unknown.

Purpose of the Study:

  • To investigate the microstructural changes in amide-modified polyethylenes.
  • To determine the location and influence of amidyl groups within the polymer matrix.

Main Methods:

  • Solid-state nuclear magnetic resonance (NMR) spectroscopy was employed.
  • NMR relaxation techniques were used to measure chain mobility in different polymer regions.
  • Analysis focused on crystalline, amorphous, and interphasial regions.

Main Results:

  • A decrease in overall crystallinity was observed with increased amidation.
  • Grafted amidyl groups were found to partition into the rigid amorphous fraction (RAF).
  • NMR provided precise assessments of functional group location within the polymer microstructure.

Conclusions:

  • Amidation alters polyethylene microstructure by concentrating functional groups in the RAF.
  • Understanding functional group localization is key to tailoring properties of functional polyolefins.
  • This study provides foundational insights into the structure-property relationships of amide-modified polyethylenes.