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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...
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Ions as Acids and Bases02:54

Ions as Acids and Bases

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Salts with Acidic Ions
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
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Acid/Base Strengths and Dissociation Constants03:02

Acid/Base Strengths and Dissociation Constants

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The relative strength of an acid or base is the extent to which it ionizes when dissolved in water. If the ionization reaction is essentially complete, the acid or base is termed strong; if relatively little ionization occurs, the acid or base is weak. There are many more weak acids and bases than strong ones. The most common strong acids and bases are listed below:
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Acid Strength and Molecular Structure03:05

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Binary Acids and Bases
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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Acidity and Basicity of Alcohols and Phenols02:36

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Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
23.0K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Aluminum monocation basicity and affinity scales.

Jean-François Gal1, Manuel Yáñez2, Otilia Mó3

  • 1Institut de Chimie de Nice, UMR CNRS 7272, Université Nice Sophia Antipolis, 06108 NICE Cedex 2, France. gal@unice.fr.

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Summary

This study reviews thermochemical data for aluminum monocation (Al+) attachment to atoms and molecules. Computational analysis provides consistent energetics and bonding insights for Al+ adducts.

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Area of Science:

  • Physical Chemistry
  • Computational Chemistry
  • Quantum Chemistry

Background:

  • Thermochemical data for aluminum monocation (Al+) interactions are crucial for understanding chemical bonding.
  • Existing literature data on Al+ affinities and basicities require consistent evaluation.

Purpose of the Study:

  • To review experimental thermochemical data for Al+ adducts.
  • To provide a consistent computational analysis of Al+ adduct energetics and structures.
  • To compare Al+ basicity with other gas-phase cations.

Main Methods:

  • Literature review of experimental thermochemical data.
  • Ab initio quantum chemical calculations at the G4 level for 43 adducts.
  • Natural bond orbital (NBO) and atoms-in-molecule (AIM) analyses for bonding insights.

Main Results:

  • Tabulated and discussed literature Al+ cation affinities (enthalpy) and basicities (Gibbs energy).
  • Consistent energetics and structural information for 43 Al+ adducts derived from G4 calculations.
  • Detailed analysis of Al(+)-ligand bonding characteristics.

Conclusions:

  • The study provides a comprehensive overview of Al+ thermochemical data.
  • Computational methods offer a consistent framework for understanding Al+ adduct formation.
  • Comparison with other cations highlights unique aspects of Al+ basicity.