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An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
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In the absence of any leveling effect, the acid strength of binary compounds of hydrogen with nonmetals (A) increases as the H-A bond strength decreases down a group in the periodic table. For group 17, the order of increasing acidity is HF < HCl < HBr < HI. Likewise, for group 16, the order of increasing acid strength is H2O < H2S < H2Se < H2Te. Across a row in the periodic table, the acid strength of binary hydrogen compounds increases with increasing...
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Leveling Effect and Non-Aqueous Acid-Base Solutions02:11

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The Leveling Effect of a Solvent
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Intermolecular Forces03:13

Intermolecular Forces

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Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen...
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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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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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Structural features of selected protic ionic liquids based on a super-strong base.

Alessandro Triolo1, Fabrizio Lo Celso2, Carlo Ottaviani1

  • 1Laboratorio Liquidi Ionici, Istituto Struttura della Materia, Consiglio Nazionale delle Ricerche, (ISM-CNR), Rome, Italy. triolo@ism.cnr.it.

Physical Chemistry Chemical Physics : PCCP
|November 12, 2019
PubMed
Summary

New protic ionic liquids (PILs) were synthesized and characterized. Hydrogen bonding significantly influences their structure and properties, with potential applications in various fields due to their ionic liquid behavior and unique fluorous domains.

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Area of Science:

  • Materials Science
  • Physical Chemistry
  • Supramolecular Chemistry

Background:

  • Protic ionic liquids (PILs) are salts that are liquid at ambient temperatures, formed by proton transfer between a Brønsted acid and a Brønsted base.
  • 1,7-diazabicyclo[5.4.0]undec-7-ene (DBU) is a strong organic base used in the synthesis of various functional materials.
  • Super-strong acids like trifluoromethanesulfonic acid (TfOH) and bis(trifluoromethanesulfonyl)imide (TFSI) are key components in designing PILs with specific properties.

Purpose of the Study:

  • To synthesize and characterize novel protic ionic liquids based on DBU and super-strong acids.
  • To investigate the chemical, physical, and structural properties of these PILs using experimental and computational methods.
  • To explore the role of hydrogen bonding and charge correlations in the morphology and potential applications of these ionic liquids.

Main Methods:

  • Synthesis of protic ionic liquids ([DBUH][TfO] and [DBUH][IM14]).
  • Experimental characterization including X-ray diffraction.
  • Computational analysis using molecular dynamics simulations.
  • Exploration of structural features, charge correlations, and hydrogen bonding interactions.

Main Results:

  • Successful preparation of two novel PILs, [DBUH][TfO] and [DBUH][IM14].
  • Demonstration of significant influence of hydrogen bonding on the morphology of the PILs.
  • Evidence for the formation of fluorous domains in the [DBUH][IM14] system.
  • Confirmation that the synthesized PILs exhibit good ionic liquid properties.

Conclusions:

  • The synthesized PILs possess favorable ionic liquid characteristics.
  • Hydrogen bonding plays a crucial role in dictating the structural organization and properties of these PILs.
  • The presence of fluorous domains in [DBUH][IM14] opens up possibilities for expanded applications, particularly in areas benefiting from phase separation or unique solvation properties.