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Updated: Feb 6, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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A quantitative definition of hypervalency.

Marcus C Durrant1

  • 1Department of Applied Sciences , Northumbria University , Newcastle-upon-Tyne , NE1 8ST , UK .

Chemical Science
|August 10, 2018
PubMed
Summary
This summary is machine-generated.

A new quantitative measure defines hypervalency using atomic charge maps. This research clarifies which molecules are truly hypervalent, revealing insights into chemical bonding and stability.

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Area of Science:

  • * Chemistry
  • * Quantum Chemistry
  • * Chemical Bonding Theory

Background:

  • * The qualitative definition of hypervalency in chemical bonding has historically presented challenges.
  • * Existing definitions struggle to provide a clear, universally accepted understanding of hypervalency.

Purpose of the Study:

  • * To develop a quantitative measure for assessing hypervalency.
  • * To re-evaluate the hypervalency of known chemical species using a new quantitative approach.
  • * To investigate the relationship between hypervalency and chemical bonding characteristics.

Main Methods:

  • * Development of a quantitative hypervalency measure based on atomic charge maps.
  • * Utilizing atomic charge maps derived from quantum calculations or experimental data.
  • * Analysis of chemical species with general formulae XFn, XCln, and XOn.

Main Results:

  • * Established a quantitative definition for hypervalency.
  • * Identified O3, CH2N2, and ClO4- as hypervalent, while XeF4, PCl5, and SO42- were found to be non-hypervalent.
  • * Demonstrated no fundamental differences in chemical bonding between hypervalent and non-hypervalent species.
  • * Correlated hypervalency with chemical instability and increased covalent bonding.

Conclusions:

  • * The developed quantitative measure provides a robust method for defining hypervalency.
  • * Hypervalency is linked to chemical instability and a higher degree of covalent character.
  • * Findings have implications for the conventional understanding of Lewis structures and chemical bonding.