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Bond Energies and Bond Lengths

Bond Energies and Bond Lengths

Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, that is, the energy necessary to separate the bonded atoms. Separating any pair of bonded atoms requires energy — the stronger a bond, the greater the energy required to break it.

Ionic Bonds

Ionic Bonds

Overview
When atoms gain or lose electrons to achieve a more stable electron configuration they form ions. Ionic bonds are electrostatic attractions between ions with opposite charges. Ionic compounds are rigid and brittle when solid and may dissociate into their constituent ions in water. Covalent compounds, by contrast, remain intact unless a chemical reaction breaks them.
Opposing Charges Hold Ions Together in Ionic Compounds
Ionic bonds are reversible electrostatic interactions between ions...

Bonding in Metals

Bonding in Metals

Metallic bonds are formed between two metal atoms. A simplified model to describe metallic bonding has been developed by Paul Drüde called the “Electron Sea Model”.

The Phosphorus Cycle

The Phosphorus Cycle

Unlike carbon, water, and nitrogen, phosphorus is not present in the atmosphere as a gas. Instead, most phosphorus in the ecosystem exists as compounds, such as phosphate ions (PO43-), found in soil, water, sediment and rocks. Phosphorus is often a limiting nutrient (i.e., in short supply). Consequently, phosphorus is added to most agricultural fertilizers, which can cause environmental problems related to runoff in aquatic ecosystems.

Covalent Bonds

Covalent Bonds

IR Spectrum Peak Intensity: Amount of IR-Active Bonds

IR Spectrum Peak Intensity: Amount of IR-Active Bonds

When infrared radiation is passed through a molecule, absorption occurs if the molecule's vibration leads to a substantial change in its bond dipole moment. Transitions between vibrational energy levels, typically corresponding to infrared frequencies (4000–400 cm−1), allow absorption if the vibration significantly alters the dipole moment, making the molecule infrared active. The molecular bonds have different stretching and bending vibrations, resulting in various peaks with...

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Updated: Jan 28, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

C-F Bond Activation Mediated by Phosphorus Compounds.

Julia M Bayne¹, Douglas W Stephan¹

¹Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, M5S 3H6, Canada.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|February 26, 2019

Summary

This review highlights phosphorus compounds for activating and functionalizing carbon-fluorine (C-F) bonds. These main-group reagents offer new routes for synthesizing valuable chemicals and materials.

Keywords:

C−F bond activation Lewis acids frustrated Lewis pairs (FLPs)hydrodefluorination phosphorus

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

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Last Updated: Jan 28, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

Laboratory-determined Phosphorus Flux from Lake Sediments as a Measure of Internal Phosphorus Loading

Laboratory-determined Phosphorus Flux from Lake Sediments as a Measure of Internal Phosphorus Loading

Published on: March 6, 2014

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

Area of Science:

Organic Chemistry
Organometallic Chemistry
Materials Science

Background:

Carbon-fluorine (C-F) bond activation is crucial for synthesizing agrochemicals, pharmaceuticals, and materials.
Transition-metal catalysts are common, but main-group alternatives are underexplored.
Phosphorus-based reagents are emerging as promising tools for C-F bond functionalization.

Purpose of the Study:

To provide an overview of C-F bond activation strategies using phosphorus compounds.
To explore the utility of P(V) and P(III) Lewis acids and P(III) Lewis bases.
To highlight applications in hydrodefluorination, C-C couplings, and C-F derivatizations.

Main Methods:

Review of literature on phosphorus-based C-F bond activation.
Focus on Lewis acid and Lewis base catalysis.
Exploration of frustrated Lewis pair (FLP) protocols.

Main Results:

Demonstration of P(V) and P(III) Lewis acids for C-F bond activation.
Utilization of P(III) Lewis bases in FLP systems for C-F transformations.
Successful hydrodefluorination, C-C coupling, and C-F derivatization reactions.

Conclusions:

Phosphorus-based reagents offer viable alternatives to transition metals for C-F bond activation.
FLP chemistry with phosphorus compounds enables diverse C-F functionalizations.
This approach expands synthetic possibilities in medicinal and materials chemistry.