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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...

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Related Experiment Video

Updated: Dec 12, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Non-Coordinated Phenolate Anions and Their Application in SF₆ Activation.

Robin F Weitkamp¹, Beate Neumann¹, Hans-Georg Stammler¹

¹Centrum für Molekulare Materialien, Fakultät für Chemie, Universität Bielefeld, Universitätsstraße 25, 33615, Bielefeld, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|August 11, 2020

Summary

Researchers created the first free phenolate anion salt using a powerful tetraphosphazene base. This new phosphazenium phenolate salt can activate the greenhouse gas sulfur hexafluoride (SF6).

Keywords:

SF6 activation hydrogen bond phenol phosphazene base weakly coordinating cation

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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:

Organometallic Chemistry
Supramolecular Chemistry
Green Chemistry

Background:

Strong bases are needed to deprotonate weakly acidic phenols.
Previous methods often resulted in hydrogen-bonded phenol-phenolate species.
Isolation of truly free phenolate anions has been challenging.

Purpose of the Study:

To synthesize and characterize a novel salt containing a free phenolate anion.
To investigate the utility of tetraphosphazene bases for phenolate salt preparation.
To explore the reactivity of the synthesized phosphazenium phenolate salt, specifically its ability to activate SF6.

Main Methods:

Reaction of phenol derivatives with a tetraphosphazene base (Schwesinger base).
Isolation and characterization of the resulting phosphazenium phenolate salt.
Electrochemical studies to determine redox potential.
Investigation of the reaction with sulfur hexafluoride (SF6).

Main Results:

Successfully synthesized the first isolable salt featuring a free phenolate anion ([H5C6-O]-).
The phosphazenium phenolate salt exhibits a redox potential of -0.72 V.
The salt selectively activates the greenhouse gas SF6 through a two-electron reduction, yielding pentafluorosulfanide ([SF5]-) and fluoride salts.

Conclusions:

Tetraphosphazene bases are highly effective for the clean synthesis of free phenolate anions.
This work provides a new route to selective synthesis of hydrogen-bonded phenol-phenolate salts.
The synthesized phosphazenium phenolate salt demonstrates potential for activating inert gases like SF6, offering new avenues in catalysis and chemical activation.