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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
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Electron delocalization refers to the distribution of electrons across multiple atoms within a molecule rather than being confined to a single atom or bond. This phenomenon is common in systems with conjugated bonds—structures where alternating single and double bonds allow π-electrons to move freely across the network. The movement of electrons stabilizes the molecule and can affect various chemical properties, including vibrational frequencies observed in IR spectroscopy.
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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
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ortho–para-Directing Deactivators: Halogens01:24

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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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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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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Beyond Strain Release: Delocalization-Enabled Organic Reactivity.

Alistair J Sterling1,2, Russell C Smith3, Edward A Anderson1

  • 1Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K.

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Strain energy release drives organic reactions, but electronic delocalization is also crucial for predicting reactivity. This principle applies to strained molecules like epoxides and aziridines, aiding in reaction prediction.

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Area of Science:

  • Organic Chemistry
  • Physical Organic Chemistry
  • Computational Chemistry

Background:

  • Strain energy release is a primary driver for many organic reactions.
  • However, strain energy alone does not fully explain reactivity differences, as seen in cyclopropanes and cyclobutanes.
  • Predicting reaction rates often requires considering factors beyond simple strain.

Purpose of the Study:

  • To investigate the role of electronic delocalization in modulating reactivity alongside strain energy.
  • To develop a predictive model for activation barriers in strained organic systems.
  • To extend the understanding of reactivity principles to various strained molecules and reactions.

Main Methods:

  • Theoretical calculations to quantify strain energy and electronic delocalization.
  • Analysis of reaction mechanisms involving strained ring systems.
  • Comparison of predicted versus experimental activation barriers.

Main Results:

  • Electronic delocalization significantly enhances or even dictates reactivity in strained molecules.
  • This principle applies to epoxides, aziridines, propellanes, and strain-driven cycloadditions.
  • A new predictive rule of thumb for activation barriers was established.

Conclusions:

  • Reactivity in strained organic systems is governed by a combination of strain release and electronic delocalization.
  • The findings provide a versatile tool for predicting reaction outcomes in organic synthesis, medicinal chemistry, and polymer science.
  • Electronic delocalization is a key concept for understanding and predicting organic reactivity.