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Ions as Acids and Bases02:54

Ions as Acids and Bases

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Salts with Acidic Ions
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Lewis Acids and Bases02:33

Lewis Acids and Bases

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In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

10.1K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
9.1K
Sharpless Epoxidation02:57

Sharpless Epoxidation

5.0K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
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Multifunctional Fe(III)-Binding Polyethers from Hydroxamic Acid-Based Epoxide Monomers.

Tobias Johann1, Ulrike Kemmer-Jonas1, Ramona D Barent1

  • 1Institute of Organic Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128, Mainz, Germany.

Macromolecular Rapid Communications
|July 30, 2019
PubMed
Summary
This summary is machine-generated.

This study synthesizes poly(ethylene glycol) (PEG) with multiple hydroxamic acids for enhanced iron binding. Block copolymers with spaced hydroxamic acids show superior Fe(III) chelation and hydrogel formation.

Keywords:
chelatorshydroxamic acidsironpoly(ethylene glycol)polyethers

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Poly(ethylene glycol) (PEG) is a versatile polymer backbone.
  • Hydroxamic acids are known for their metal-chelating properties.
  • Developing functional polymers with controlled architectures is crucial for advanced applications.

Purpose of the Study:

  • To synthesize novel PEG-based copolymers functionalized with multiple hydroxamic acids.
  • To investigate the effect of polymer architecture and hydroxamic acid spacing on Fe(III) chelation.
  • To explore the potential of these polymers in forming networks and hydrogels.

Main Methods:

  • Copolymerization of ethylene oxide with a protected hydroxamic acid epoxide monomer (HAAGE).
  • Synthesis of statistical, diblock (AB), and triblock (ABA) copolymers with controlled molecular weights and low dispersities.
  • Deprotection of hydroxamic acids using mild acidic treatment.
  • Evaluation of Fe(III) binding efficiency and hydrogel formation capabilities.

Main Results:

  • Successfully synthesized various PEG-HAAGE copolymers (statistical, AB, ABA) with molecular weights from 2600 to 12,000 g/mol and dispersities < 1.2.
  • Demonstrated that a minimum spacing of 5 ethylene glycol units between hydroxamic acids is essential for efficient Fe(III) binding.
  • Identified block copolymers as optimal architectures for creating polymer networks and hydrogels through Fe(III) chelation.

Conclusions:

  • Novel PEG-based polymers with multiple, accessible hydroxamic acid groups have been developed.
  • Polymer architecture significantly influences metal-chelating efficiency, with block copolymers showing superior performance.
  • These functional polymers hold promise for applications in hydrogel formation and metal ion sequestration.