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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
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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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Anionic Chain-Growth Polymerization: Overview01:20

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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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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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Preparation of Amides

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
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Pressure-Induced Amidine Formation via Side-Chain Polymerization in a Charge-Transfer Cocrystal.

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Compressing molecules can create unique nanomaterials. Functionalizing arenes lowers reaction pressure, but side reactions, like amidine formation, can compete with desired cycloaddition, impacting material synthesis.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • Solid-state reactions under compression offer unique synthetic routes for nanomaterials.
  • Topochemical-like reactions of arenes are of interest for polymer synthesis.
  • High onset pressures and poor selectivity limit current compression-based reactions.

Purpose of the Study:

  • To explore functionalization of π-stacked arenes to lower reaction barriers and onset pressures for cycloaddition.
  • To investigate competing side-chain reactions in functionalized arenes under compression.
  • To understand the reaction pathways in a diaminobenzene:tetracyanobenzene cocrystal.

Main Methods:

  • Vibrational spectroscopy
  • X-ray diffraction
  • First-principles calculations

Main Results:

  • Incorporating electron-withdrawing and -donating groups theoretically reduces cycloaddition barriers.
  • Amidine formation between amine and cyano groups occurred before cycloaddition at ~9 GPa in the model system.
  • Competing side-chain reactions were observed, demonstrating alternative pathways.

Conclusions:

  • Strategic functionalization can enable reduced-barrier cycloaddition reactions in the solid state.
  • Pendant groups on arenes can lead to alternative, competing reaction pathways.
  • Controlled reactions of pendant groups offer a new strategy for synthesizing novel polymeric nanomaterials.