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Related Concept Videos

Weak Base Solutions03:21

Weak Base Solutions

26.6K
Some compounds produce hydroxide ions when dissolved by chemically reacting with water molecules. In all cases, these compounds react only partially and so are classified as weak bases. These types of compounds are also abundant in nature and important commodities in various technologies. For example, global production of the weak base ammonia is typically well over 100 metric tons annually, being widely used as an agricultural fertilizer, a raw material for chemical synthesis of other...
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Titration of a Weak Base with a Strong Acid01:20

Titration of a Weak Base with a Strong Acid

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The titration curve of a weak base like ammonia with a strong acid like hydrochloric acid is the mirror image of the titration curve of a weak acid with a strong base.
Using the ICE table and substituting the Kb value, we calculate the initial pH of 50 mL of 0.1 M ammonia to be 11.11. Addition of 25 mL of 0.1 M hydrochloric acid to this solution of ammonia results in a buffer with an equal concentration of ammonia and ammonium ions. The pH of this buffer can be calculated by substituting these...
9.4K
Determining the pH of Salt Solutions04:08

Determining the pH of Salt Solutions

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The pH of a salt solution is determined by its component anions and cations. Salts that contain pH-neutral anions and the hydronium ion-producing cations form a solution with a pH less than 7. For example, in ammonium nitrate (NH4NO3) solution, NO3− ions do not react with water whereas NH4+ ions produce the hydronium ions resulting in the acidic solution.  In contrast, salts that contain pH-neutral cations and the hydroxide ion-producing anions form a solution with a pH greater than 7. For...
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Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

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Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of nonbonding electrons, aliphatic amines can also act as Lewis bases by forming a covalent bond with an electrophile.
To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates higher...
7.1K
Common Ion Effect03:24

Common Ion Effect

47.9K
Compared with pure water, the solubility of an ionic compound is less in aqueous solutions containing a common ion (one also produced by dissolution of the ionic compound). This is an example of a phenomenon known as the common ion effect, which is a consequence of the law of mass action that may be explained using Le Châtelier’s principle. Consider the dissolution of silver iodide:
47.9K
Weak Acid Solutions04:02

Weak Acid Solutions

45.0K
Few compounds act as strong acids. A far greater number of compounds behave as weak acids and only partially react with water, leaving a large majority of dissolved molecules in their original form and generating a relatively small amount of hydronium ions. Weak acids are commonly encountered in nature, being the substances partly responsible for the tangy taste of citrus fruits, the stinging sensation of insect bites, and the unpleasant smells associated with body odor. A familiar example of a...
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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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A pH Scale for the Protic Ionic Liquid Ethylammonium Nitrate.

Ryo Kanzaki1, Hitoshi Kodamatani2, Takashi Tomiyasu2

  • 1Graduate School of Science and Engineering, Kagoshima University, 1-21-35, Korimoto, Kagoshima, 890-0065, Japan. kanzaki@sci.kagoshima-u.ac.jp.

Angewandte Chemie (International Ed. in English)
|April 14, 2016
PubMed
Summary

Protic ionic liquids (PILs) like ethylammonium nitrate (EAN) can serve as acid-base media. The pKa values of compounds in EAN are approximately one unit higher than in water, indicating a different acidity scale.

Keywords:
acid-base catalysisacidityionic liquidspH scalepotentiometric titrations

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Area of Science:

  • Chemistry
  • Physical Chemistry
  • Ionic Liquids

Background:

  • Protic ionic liquids (PILs) are salts that are liquid at ambient temperatures and contain transferable protons.
  • PILs are being explored as alternative reaction media due to their unique properties, including tunable acidity and basicity.
  • Understanding the acid-base properties of PILs is crucial for their application in chemical synthesis and catalysis.

Purpose of the Study:

  • To quantify the acid-base properties of protic ionic liquids (PILs) as reaction media.
  • To compare the pKa values of various compounds in a neat PIL (ethylammonium nitrate, EAN) with their pKa values in water.
  • To investigate the factors influencing the observed differences in pKa values.

Main Methods:

  • Potentiometric titrations were performed in neat ethylammonium nitrate (EAN).
  • pKa values of 12 different compounds were measured in EAN.
  • The obtained pKa values in EAN were linearly correlated with their known pKa values in water.

Main Results:

  • A linear relationship was observed between pKa values in EAN and water for 12 compounds.
  • The pKa values in EAN were consistently higher by approximately one unit compared to water, irrespective of compound charge or hydrophobicity.
  • The observed shift in pKa is potentially attributed to the stronger acidity of nitric acid in EAN compared to hydronium ions in water.

Conclusions:

  • Ethylammonium nitrate (EAN) exhibits distinct acid-base properties compared to water.
  • The acidity scale in EAN differs from the conventional aqueous pH scale, with a range comparable to -1 to 9 on the water-based pH scale.
  • PILs offer a versatile platform for modulating acid-base chemistry, with potential implications for reaction design and optimization.