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Manipulating solute nucleophilicity with room temperature ionic liquids.

Lorna Crowhurst1, N Llewellyn Lancaster, Juan M Pérez-Arlandis

  • 1Contribution from the Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, United Kingdom.

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Ionic liquids enhance the nucleophilicity of amines, unlike their deactivating effect on chloride ions. This reactivity difference is primarily due to altered activation entropies and solvent hydrogen-bonding properties.

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Area of Science:

  • Physical Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Ionic liquids (ILs) are tunable solvents with unique properties.
  • Understanding ILs' effect on nucleophilic reactions is crucial for synthetic chemistry.
  • Charge-neutral nucleophiles' behavior in ILs is less explored than ionic ones.

Purpose of the Study:

  • To investigate the impact of ILs on the reactivity of charge-neutral amine nucleophiles.
  • To compare the nucleophilicity of amines in ILs versus molecular solvents.
  • To elucidate the factors governing these reactivity changes.

Main Methods:

  • Studied reactions of (n)butylamine, di-(n)butylamine, and tri-(n)butylamine with methyl p-nitrobenzenesulfonate.
  • Utilized three ionic liquids: [bmpy][N(Tf)(2)], [bmpy][OTf], and [bmim][OTf].
  • Compared reactivities in ILs with those in dichloromethane and acetonitrile; analyzed Eyring activation parameters and Kamlet-Taft solvent parameters.

Main Results:

  • All studied amines exhibited enhanced nucleophilicity in ionic liquids compared to molecular solvents.
  • Ionic liquids deactivated chloride ion nucleophiles, contrasting with amine behavior.
  • Activation entropy changes were identified as the primary driver for observed reactivity trends.

Conclusions:

  • Ionic liquids significantly modulate the reactivity of charge-neutral nucleophiles.
  • Hydrogen-bonding interactions between ILs and nucleophiles play a key role in observed effects.
  • The distinct effects of ILs on charged vs. neutral nucleophiles highlight their complex solvation behavior.