G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues

Mark L.G. Borst, Andreas W. Ehlers, Koop Lammertsma

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)


The ring strain present in 2-aza-1-phosphabicyclo[n.1.0]alka(e)nes (n = 1-5) is calculated at the G3(MP2) level using homodesmotic reactions. The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring systems. It is shown that the strain caused by fusion with a cyclopropane is the sum of the separate rings, whereas the strain resulting from fusion with cyclopropene leads to strain energies much larger than the sum of rings, as a result of the inverted nature of the bridgehead carbon. In all ring structures but one, cyclohexane, substitution by nitrogen and phosphorus is favorable and the effect is most pronounced for the most condensed structures. The calculated strain energies correlate very well with the experimental stability and reactivity of the bicyclic iron-amino phosphirane and phosphirene complexes.

Original languageEnglish
Pages (from-to)8110-8116
Number of pages7
JournalJournal of Organic Chemistry
Issue number20
Publication statusPublished - 20 Sept 2005
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


Dive into the research topics of 'G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues'. Together they form a unique fingerprint.

Cite this