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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Base-Catalyzed Ring-Opening of Epoxides02:26

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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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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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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
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Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

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The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Cationic Ring-Opening Polymerization of 2-Propyl-2-oxazolines: Understanding Structural Effects on Polymerization

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Cationic ring-opening polymerization rates differ significantly between cyclopropyl, n-propyl, and isopropyl oxazolines. Electrostatic effects, specifically monomer nucleophilicity, drive these observed reactivity differences.

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Area of Science:

  • Polymer Chemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • Cationic ring-opening polymerization (CROP) is a vital method for synthesizing polymers.
  • Understanding monomer structure-reactivity relationships is crucial for controlling polymerization kinetics.

Purpose of the Study:

  • Investigate the surprising differences in CROP rates among 2-cyclopropyl-2-oxazoline (c-PropOx), 2-n-propyl-2-oxazoline (n-PropOx), and 2-isopropyl-2-oxazoline (i-PropOx).
  • Determine the underlying factors controlling the observed polymerization kinetics.

Main Methods:

  • Experimental measurement of polymerization kinetics in acetonitrile at 140 °C.
  • Theoretical free energy calculations.
  • Density Functional Theory (DFT) based analysis of reactivity descriptors, electrostatics, and frontier molecular orbitals.

Main Results:

  • Polymerization rate constants (kp) decreased in the order: c-PropOx > n-PropOx > i-PropOx.
  • Theoretical calculations confirmed the experimental trend for kp.
  • Electrostatic effects were identified as the primary driver of reactivity differences.

Conclusions:

  • The nucleophilicity of the oxazoline monomer, influenced by the charge on the nitrogen atom, dictates the polymerization rate.
  • The most negative nitrogen charge in c-PropOx corresponds to its highest reactivity.
  • Electrophilicity of the propagating cation showed minimal variation, reinforcing monomer nucleophilicity as the key factor.