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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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 amide...
Glycosaminoglycans01:23

Glycosaminoglycans

Glycosaminoglycans (GAGs), also known as mucopolysaccharides, are long and linear polymers comprising of specific repeating disaccharides - the amino sugar that can be N-acetylglucosamine or N-acetylgalactosamine, and a uronic acid that is usually glucuronic acid or iduronic acid.
GAGS are found in the extracellular matrix of vertebrates, invertebrates, and bacteria. Due to their polar nature they attract water, and serve as excellent lubricants or shock absorbers in an animal body.
Hyaluronic...
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
Proteoglycans01:05

Proteoglycans

Glycans, a class of complex heterogeneous molecules, can be covalently attached to proteins to form glycosylated proteins that regulate various physiological and pathological processes. Glycosylated proteins or glycoproteins comprise N-linked and O-linked oligosaccharides. O-glycosylation is the most common type of protein glycosylation. Here, glycans attach to the oxygen atom of the hydroxyl groups of Serine or Threonine residues. O-linked glycosylation occurs later in protein processing,...
Peptidoglycan Synthesis01:28

Peptidoglycan Synthesis

Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan biosynthesis begins in...
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

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...

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Related Experiment Video

Updated: May 27, 2026

Studying the Effects of Matrix Stiffness on Cellular Function using Acrylamide-based Hydrogels
10:19

Studying the Effects of Matrix Stiffness on Cellular Function using Acrylamide-based Hydrogels

Published on: August 10, 2010

N-Acryloyl glycinamide.

Jan Seuring1, Seema Agarwal, Klaus Harms

  • 1Philipps Universität Marburg, Fachbereich Chemie, Hans-Meerwein-Strasse, D-35032 Marburg, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|November 18, 2011
PubMed
Summary

This study details N-(carbamoylmethyl)prop-2-enamide, a molecule that forms thermoresponsive polymers in water. Its crystal structure reveals linked planar segments and a 2D network formed by hydrogen bonding.

Area of Science:

  • Polymer Chemistry
  • Crystallography
  • Materials Science

Background:

  • Thermoresponsive polymers exhibit temperature-dependent solubility, crucial for applications like drug delivery and smart materials.
  • Understanding monomer structure is key to controlling polymer properties.

Purpose of the Study:

  • To characterize the crystal structure of N-(carbamoylmethyl)prop-2-enamide.
  • To investigate the structural basis for its radical polymerization and thermoresponsive behavior.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.
  • Analysis of bond lengths, angles, and intermolecular interactions (hydrogen bonding).

Main Results:

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  • The molecule consists of linked, essentially planar acrylamide and amide segments with a dihedral angle of 81.36°.
  • N-H⋯O hydrogen bonding in the crystal structure forms an infinite two-dimensional network along the (100) direction.
  • Conclusions:

    • The unique structure of N-(carbamoylmethyl)prop-2-enamide supports its polymerization into thermoresponsive polymers.
    • The observed crystal packing and hydrogen bonding provide insights into the intermolecular forces governing the material's behavior.