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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
What is Organic Chemistry?02:17

What is Organic Chemistry?

Organic chemistry is the study of compounds of carbon called organic compounds. Organic compounds either originate from living organisms or are synthesized by chemists. A defining trait of these compounds is the presence of carbon as the principal element, which is bonded to other carbon atoms and other elements such as hydrogen, oxygen, nitrogen, and sulfur. The existence of a wide array of organic molecules is a consequence of carbon atoms’ ability to form up to four strong bonds to other...
Keto–Enol Tautomerism: Mechanism01:14

Keto–Enol Tautomerism: Mechanism

The keto and enol forms are known as tautomers and they constantly interconvert (or tautomerize) between the two forms under acid or base catalyzed conditions. Both the reactions involve the same steps—protonation and deprotonation— although in the reverse order.

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Related Experiment Video

Updated: May 23, 2026

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes
09:42

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes

Published on: January 16, 2016

Atom tunneling in organic transformations.

Frederic W Patureau1

  • 1Fachbereich Chemie, Technische Universität Kaiserslautern, Germany. patureau@chemie.uni-kl.de

Angewandte Chemie (International Ed. in English)
|March 23, 2012
PubMed
Summary

Atoms like hydrogen can tunnel, disappearing and reappearing in molecules. This quantum tunneling phenomenon explains isomerization in compounds like carboxylic acids and is relevant to chemical reactions.

Area of Science:

  • Quantum chemistry
  • Physical organic chemistry

Background:

  • Atoms in molecules can change positions, a process known as isomerization.
  • Quantum mechanical effects, such as tunneling, are increasingly recognized as important in chemical transformations.

Purpose of the Study:

  • To highlight the phenomenon of atom tunneling in chemical structures.
  • To explain how atom tunneling contributes to molecular isomerization.

Main Methods:

  • Theoretical calculations and computational modeling can be used to study atom tunneling.
  • Spectroscopic techniques can provide evidence for tunneling events.

Main Results:

  • Atoms, including hydrogen and deuterium, can tunnel across potential energy barriers within molecules.

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Last Updated: May 23, 2026

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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
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  • Atom tunneling is a key mechanism for the isomerization of certain molecules, such as carboxylic acids and hydroxycarbenes.

    • Conclusions:

    • Atom tunneling is a significant quantum effect in chemistry.
    • Understanding tunneling is crucial for predicting and controlling chemical reactions.