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Related Concept Videos

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Hydrogen Bonds00:26

Hydrogen Bonds

Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared.

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Determination of the Photoisomerization Quantum Yield of a Hydrazone Photoswitch
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Published on: February 7, 2022

Halogen bond-driven azo-hydrazone tautomerisation: a computational study.

Antti Siiskonen1, Arri Priimagi2

  • 1Faculty of Engineering and Natural Sciences, Smart Photonic Materials, Tampere University, Korkeakoulunkatu 3, Tampere, 33720, Finland.

Journal of Molecular Modeling
|May 7, 2026
PubMed
Summary
This summary is machine-generated.

Halogen bonding influences azo-hydrazone tautomerization in azobenzenes, potentially inverting tautomeric preference and enabling tunable sensing applications. This study explores halogen bonding effects on hydroxyazobenzenes and related compounds.

Keywords:
AzobenzeneDensity functional theoryHalogen bondingTautomerisation

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Area of Science:

  • Supramolecular Chemistry
  • Computational Chemistry
  • Materials Science

Background:

  • Azo-hydrazone tautomerization impacts azobenzene photoswitching and properties.
  • Non-covalent interactions, like halogen bonding, can alter tautomeric equilibrium.
  • Understanding these interactions is key for designing functional azobenzene systems.

Purpose of the Study:

  • Investigate the influence of halogen bonding on azo-hydrazone tautomerization in hydroxyazobenzenes and azonaphthalene derivatives.
  • Examine the role of alkoxy groups in modulating tautomerization and halogen bonding.
  • Explore self-complementary halogen-bonded dimers for potential sensing applications.

Main Methods:

  • Density functional theory (DFT) calculations using M06-2X/DGDZVP.
  • Geometry optimizations and interaction energy calculations.
  • Analysis of wavefunctions using AIMAll for interacting quantum atom analysis.

Main Results:

  • Halogen bonding generally favors the hydrazone tautomer.
  • Tautomeric preference can be inverted when the azo tautomer is only slightly more stable.
  • Temperature affects halogen bonding strength and tautomeric equilibrium.

Conclusions:

  • Halogen bonding offers a tunable mechanism to control azo-hydrazone tautomerization.
  • These systems show promise for developing novel sensing platforms.
  • Methoxy and nitro groups influence halogen bonding and tautomerization.