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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
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In acid-base chemistry, the leveling effect refers to the limitation imposed by the solvent on the strength of acids and bases in solution. When a base stronger than the solvent's conjugate base is used, it deprotonates the solvent until the base is entirely consumed, making it ineffective against weaker acids. Conversely, an acid stronger than the solvent's conjugate acid protonates the solvent until the acid is depleted, rendering it ineffective against weaker bases. Essentially, the...
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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
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Concurrent base and silver(I) catalysis pulsed by fuel acid.

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Researchers treated a silver(I)-loaded cyclam derivative with acid, creating a new state. This new state enabled two catalytic reactions, a Michael addition and an oxime cyclization, under specific conditions.

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Area of Science:

  • Supramolecular Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Crown ether receptors and cyclam derivatives are key components in host-guest chemistry and metal ion complexation.
  • Silver(I) ions play crucial roles in various catalytic processes.
  • Understanding the dynamic behavior of metal-loaded supramolecular systems is essential for developing novel catalysts.

Purpose of the Study:

  • To investigate the reversible transformation of a silver(I)-loaded cyclam derivative upon treatment with acid.
  • To explore the catalytic activity of the transformed supramolecular system under dissipative conditions.
  • To demonstrate the potential for controlled catalysis through dynamic changes in molecular states.

Main Methods:

  • Synthesis and characterization of a silver(I)-loaded cyclam derivative and a crown-ether receptor.
  • Acid-induced reversible transformation between two distinct supramolecular states (NetState-I and NetState-II).
  • In situ monitoring of catalytic reactions, including base-catalyzed Michael addition and silver(I)-catalyzed oxime cyclization, within the transformed system.

Main Results:

  • Reversible conversion of the initial silver(I)-loaded cyclam derivative (NetState-I) to a silver(I)-loaded crown ether (NetState-II) upon acid treatment.
  • NetState-I exhibited no catalytic activity, while NetState-II facilitated both Michael addition and oxime cyclization reactions.
  • Catalysis was successfully initiated and sustained under dissipative conditions, highlighting the role of the dynamic system.

Conclusions:

  • The study demonstrates a novel method for controlling catalytic activity through the reversible transformation of a supramolecular system.
  • The developed system offers a platform for switchable catalysis, where different reactions can be accessed by altering the system's state.
  • This work has implications for the design of responsive catalytic materials and self-processing chemical systems.