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Basicity of Aliphatic Amines

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...

Overview of Functional Groups

Overview of Functional Groups

Functional groups are a group of atoms with characteristic properties, which when linked to the carbon skeleton of a molecule, alter the properties of that molecule. For example, certain functional groups will make a molecule hydrophilic, whereas others will make them hydrophobic. These functional groups are an indispensable part of organic chemistry and important components of biological molecules, such as carbohydrates, proteins, lipids, and nucleic acids. Each functional group is a unique...

Acidity and Basicity of Alcohols and Phenols

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.

Acidity and Basicity of Carboxylic Acid Derivatives

Acidity and Basicity of Carboxylic Acid Derivatives

Carboxylic acids are the strongest among organic acids, as they readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion. In comparison, the acid derivatives lack acidic hydrogens directly attached to a functional group. In these compounds, the acidic nature arises from their ability to lose α hydrogens, making them weakly acidic.
The relative acidic strength of the derivatives can be explained based on the extent of resonance stabilization of the conjugate base. The...

Overview of Advanced Functional Groups

Overview of Advanced Functional Groups

Functional groups are groups of atoms with specific chemical properties that occur within organic molecules and are sometimes denoted as “R”. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
Types of Advanced Functional Groups
The table below summarizes some of the major functional groups in organic chemistry.

Acidity of Carboxylic Acids

Acidity of Carboxylic Acids

Carboxylic acids are the strongest organic acids. However, their acidic strength is much less than mineral acids like HCl. Carboxylic acids ionize in water and readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion.

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Determination of the Gas-phase Acidities of Oligopeptides

Determination of the Gas-phase Acidities of Oligopeptides

Published on: June 24, 2013

Gas-phase basicities of polyfunctional molecules. Part 4: Carbonyl groups as basic sites.

¹Département de Chimie, Laboratoire des Mécanismes Réactionnels, Ecole Polytechnique, 91120, Palaiseau, France.

Mass Spectrometry Reviews

|January 9, 2014

Summary

This review examines gas-phase protonation thermochemistry for carbonyl-containing polyfunctional molecules. It analyzes ketones, acids, and derivatives, providing re-evaluated experimental data and computational insights.

Keywords:

intramolecular hydrogen bonds mass spectrometry protonation quantum chemical calculations substituent effects thermochemistry

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Area of Science:

Physical Chemistry
Computational Chemistry
Organic Chemistry

Background:

This article is the fourth in a series reviewing gas-phase protonation thermochemistry of polyfunctional molecules.
Previous parts covered theory, saturated basic sites, and amino acids.

Purpose of the Study:

To review the gas-phase protonation thermochemistry of carbonyl-containing polyfunctional molecules.
To examine specific examples including ketones, acids, and their derivatives.

Main Methods:

Review of experimental data on gas-phase basicity.
Re-evaluation of experimental data using an adopted basicity scale.
Application of G3 and G4 quantum chemistry computations for structural and energetic analysis.

Main Results:

Detailed examination of aliphatic and unsaturated ketones, diketones, ketoalcohols, and ketoethers.
Analysis of protonation energetics for gaseous acids and derivatives (diacids, diesters, diamides, anhydrides, imides, ureas, carbamates, amino acid derivatives, peptides).
Presentation of structural and energetic information from quantum chemical computations.

Conclusions:

Provides a comprehensive overview of protonation energetics for a wide range of carbonyl-containing compounds.
Integrates experimental data with theoretical calculations to enhance understanding.
Establishes a re-evaluated basicity scale for these molecules.