Related Experiment Video
Updated: Jun 22, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
White phosphorus is air-stable within a self-assembled tetrahedral capsule
Prasenjit Mal1, Boris Breiner, Kari Rissanen
1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
Abstract:
The air-sensitive nature of white phosphorus underlies its destructive effect as a munition: Tetrahedral P4 molecules readily react with atmospheric dioxygen, leading this form of the element to spontaneously combust upon exposure to air. Here, we show that hydrophobic P4 molecules are rendered air-stable and water-soluble within the hydrophobic hollows of self-assembled tetrahedral container molecules, which form in water from simple organic subcomponents and iron(II) ions. This stabilization is not achieved through hermetic exclusion of O2 but rather by constriction of individual P4 molecules; the addition of oxygen atoms to P4 would result in the formation of oxidized species too large for their containers. The phosphorus can be released in controlled fashion without disrupting the cage by adding the competing guest benzene.
Related Concept Videos
The Phosphorus Cycle
Hybridization of Atomic Orbitals II
VSEPR Theory and the Basic Shapes
Predicting Molecular Geometry
Hybridization of Atomic Orbitals I
Cell Inclusions
