Diradical

---

title: "Diradical" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["inorganic-chemistry", "magnetism", "organic-chemistry"] description: "Chemical species with two electrons occupying degenerate molecular orbitals" topic_path: "science/chemistry" source: "https://en.wikipedia.org/wiki/Diradical" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical species with two electrons occupying degenerate molecular orbitals ::

In chemistry, a diradical is a molecular species with two electrons occupying molecular orbitals (MOs) which are degenerate. The term "diradical" is mainly used to describe organic compounds, where most diradicals are extremely reactive and non-Kekulé molecules that are rarely isolated. Diradicals are even-electron molecules but have one fewer bond than the number permitted by the octet rule.

Examples of diradical species can also be found in coordination chemistry, for example among bis(1,2-dithiolene) metal complexes.

Spin states

Diradicals are usually triplets. The phrases singlet and triplet are derived from the multiplicity of states of diradicals in electron spin resonance: a singlet diradical has one state (S=0, Ms=20+1=1, ms=0) and exhibits no signal in EPR and a triplet diradical has 3 states (S=1, Ms=21+1=3, ms=-1; 0; 1) and shows in EPR 2 peaks (if no hyperfine splitting). The triplet state has total spin quantum number S=1 and is paramagnetic. Therefore, diradical species display a triplet state when the two electrons are unpaired and display the same spin. When the unpaired electrons with opposite spin are antiferromagnetically coupled, diradical species can display a singlet state (S=0) and be diamagnetic.

Examples

Stable, isolable, diradicals include singlet oxygen and triplet oxygen. Other important diradicals are certain carbenes, nitrenes, and their main-group elemental analogues. Lesser-known diradicals are nitrenium ions, carbon chains, and organic so-called non-Kekulé molecules in which the electrons reside on different carbon atoms. Main-group cyclic structures can also exhibit diradicals, such as disulfur dinitride, or diradical character, such as diphosphadiboretanes. In inorganic chemistry, both homoleptic and heteroleptic 1,2-dithiolene complexes of d8 transition metal ions show a large degree of diradical character in the ground state.

Diradicals in which the unpaired electrons nevertheless interact are sometimes referred to as diradicaloids.

References

References

1. "Diradicals".
2. (September 2013). "Diradicals". Chemical Reviews.
3. (December 2020). "Diradical Character of Neutral Heteroleptic Bis(1,2-dithiolene) Metal Complexes: Case Study of [Pd(Me₂timdt)(mnt)] (Me₂timdt=1,3-Dimethyl-2,4,5-trithioxoimidazolidine; mnt^2-=1,2-Dicyano-1,2-ethylenedithiolate)". Inorganic Chemistry.
4. (July 2005). "Electronic structure of square planar bis(benzene-1,2-dithiolato)metal complexes M(L)(2) (z=2-, 1-, 0; M=Ni, Pd, Pt, Cu, Au): an experimental, density functional, and correlated ab initio study". Inorganic Chemistry.
5. "Triplet State".
6. (August 2002). "Theoretical evidence for the singlet diradical character of square planar nickel complexes containing two o-semiquinonato type ligands". Inorganic Chemistry.
7. (2021-01-13). "Isolation of a Ge(I) Diradicaloid and Dihydrogen Splitting". Journal of the American Chemical Society.
8. (July 2017). "Effect of Li Termination on the Electronic and Hydrogen Storage Properties of Linear Carbon Chains: A TAO-DFT Study". Scientific Reports.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::