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Related Concept Videos

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

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

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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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Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Energy Diagrams, Transition States, and Intermediates

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Free-energy diagrams, or reaction coordinate diagrams, are graphs showing the energy changes that occur during a chemical reaction. The reaction coordinate represented on the horizontal axis shows how far the reaction has progressed structurally. Positions along the x-axis close to the reactants have structures resembling the reactants, while positions close to the products resemble the products.  Peaks on the energy diagram represent stable structures with measurable lifetimes, while...
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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
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SN2 Reaction: Transition State

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An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
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Updated: Dec 7, 2025

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Excited State Anions in Organic Transformations.

Matthias Schmalzbauer1, Michela Marcon1, Burkhard König1

  • 1Faculty of Chemistry and Pharmacy, University of Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany.

Angewandte Chemie (International Ed. in English)
|October 1, 2020
PubMed
Summary

Photoexcited closed-shell anions offer unique reactivity for organic synthesis. This review highlights their potential in sustainable chemistry, expanding the synthetic toolbox with novel single electron transfer reactions.

Keywords:
electron transferexcited anionsphotoredox catalysisphotoreductionsynthetic photochemistry

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Area of Science:

  • Photochemistry
  • Organic Synthesis
  • Sustainable Chemistry

Background:

  • Light-driven chemical transformations offer selective energy input.
  • Open-shell intermediates provide novel synthetic routes.
  • Direct conversion of unactivated compounds is a key goal for sustainability.

Purpose of the Study:

  • To review the characteristics of anionic photochemistry.
  • To highlight pioneering work in the field.
  • To showcase recent progress in utilizing photoexcited anions for organic synthesis.

Main Methods:

  • Discussion of anionic photochemistry principles.
  • Review of seminal and recent research studies.
  • Analysis of excited-state reactivity and single electron transfer.

Main Results:

  • Photoexcited closed-shell anions exhibit extreme potentials for single electron transfer.
  • Anions display unusual excited-state reactivity.
  • Limited examples of their use as reagents or photocatalysts exist.

Conclusions:

  • Anionic photochemistry presents a promising avenue for expanding synthetic methodologies.
  • Further exploration of photoexcited anions can lead to more sustainable and atom-economic chemical processes.
  • This field holds significant potential for innovation in organic synthesis.