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Related Concept Videos

Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

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...
Acid Strength and Molecular Structure03:05

Acid Strength and Molecular Structure

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...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

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.
Polyprotic Acids03:38

Polyprotic Acids

Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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).
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...

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Determination of the Gas-phase Acidities of Oligopeptides
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Published on: June 24, 2013

Gas-phase basicities of polyfunctional molecules. Part 2: Saturated basic sites.

Guy Bouchoux1, Jean-Yves Salpin

  • 1Ecole Polytechnique, Laboratoire des Mécanismes Réactionnels (DCMR), Département de Chimie, 91120 Palaiseau, France. bouchoux@dcmr.polytechnique.fr

Mass Spectrometry Reviews
|July 21, 2011
PubMed
Summary

This review examines the gas-phase protonation thermochemistry of polyfunctional molecules with saturated basic sites. It details the energetic and structural aspects of protonation for various nitrogen and oxygen-containing compounds.

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Area of Science:

  • Physical Chemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • This article is the second part of a review on gas-phase protonation thermochemistry.
  • The first part covered concepts and methods for determining gas-phase basicity.
  • This section focuses on specific examples of protonation in polyfunctional molecules.

Purpose of the Study:

  • To examine specific examples of gas-phase protonation in polyfunctional molecules.
  • To investigate the structural and energetic aspects of protonation for molecules with saturated basic sites.
  • To provide a comprehensive overview of protonation thermochemistry for various compound classes.

Main Methods:

  • Review of experimental and theoretical methods for determining gas-phase basicity.
  • Analysis of structural and energetic data related to protonation.
  • Examination of specific classes of polyfunctional molecules.

Main Results:

  • Detailed examination of gas-phase protonation for aliphatic, cyclic, and aromatic poly-amines.
  • Analysis of protonation thermochemistry for amino alcohols, alcohols, ethers, and hydroxyl-ethers.
  • Emphasis on the role of saturated nitrogen and oxygen atoms in protonation.

Conclusions:

  • Protonation thermochemistry varies significantly across different classes of polyfunctional molecules.
  • The nature of saturated basic sites (N, O) influences protonation energetics.
  • This review provides valuable data for understanding molecular interactions and reactivity in the gas phase.