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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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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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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,...
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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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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Anion-π catalysis.

Yingjie Zhao1, César Beuchat, Yuya Domoto

  • 1Department of Organic Chemistry, University of Geneva , Geneva, Switzerland.

Journal of the American Chemical Society
|January 25, 2014
PubMed
Summary
This summary is machine-generated.

This study demonstrates anion-π catalysis, where specific interactions stabilize transition states in chemical reactions. This discovery opens new avenues for designing innovative catalysts for reactions involving anionic transition states.

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Area of Science:

  • Catalysis
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Noncovalent interactions are crucial for developing functional molecular systems.
  • Anion-π interactions, a specific type of noncovalent interaction, have potential applications in catalysis.
  • The Kemp elimination reaction serves as a model system for investigating new catalytic mechanisms.

Purpose of the Study:

  • To provide experimental and theoretical evidence for anion-π interactions in catalysis.
  • To explore the design of novel catalysts utilizing anion-π interactions for reactions with anionic transition states.
  • To quantify the transition-state stabilization and catalytic proficiency achieved through anion-π catalysis.

Main Methods:

  • Utilizing the Kemp elimination reaction to test catalyst performance.
  • Synthesizing naphthalenediimide-based catalysts with covalently attached carboxylate bases and solubilizers.
  • Employing experimental techniques to measure transition-state stabilization (ΔΔGTS), substrate recognition (KM), and catalytic proficiency.
  • Conducting computational simulations to corroborate experimental findings and elucidate interaction mechanisms.

Main Results:

  • Achieved significant transition-state stabilization (up to ΔΔGTS = 31.8 ± 0.4 kJ mol⁻¹) via anion-π interactions on π-acidic surfaces.
  • Demonstrated a direct correlation between increased π-acidity and enhanced transition-state stabilization, confirming anion-π catalysis.
  • Observed that substrate recognition (KM) was not significantly improved by increasing π-acidity, distinguishing it from transition-state stabilization.
  • Found that linker design between the π-acidic surface and the carboxylate base critically impacts catalytic activity.

Conclusions:

  • Anion-π interactions effectively stabilize anionic transition states, leading to catalysis.
  • The π-acidity of the catalyst surface is a key factor in achieving high transition-state stabilization.
  • Catalyst linker optimization and intramolecular interactions play significant roles in anion-π catalysis efficiency.