Rearrangement of the 1-oxaspiro[4.5]deca-6,9-dien-8-ylium ion. Part 1. A semiempirical (AM1), density functional and ab initio molecular orbital computational study

C W McCleland, G D Ruggiero, I H Williams

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The energetics of the ring-expanding rearrangement of the 1-oxaspiro[4.5]deca-6,9-dien-8-ylium ion 14 involving a 1,2-shift of either carbon or oxygen have been investigated through molecular orbital calculations at the semiempirical (AM1), ab initio (HF/z, HF/6-31G* and MP2/6-31G*) and density functional (B3LYP/6-31G*) levels of approximation. Our results have shown that rearrangement via migration by carbon is thermodynamically (and probably also kinetically) favoured over the alternative 1,2-shift by oxygen. The geometries and charge distributions computed for the structure 14 as well as the rearranged cations and possible transition structures are also described.
Original languageEnglish
Pages (from-to)204-208
Number of pages5
JournalJournal of the Chemical Society: Perkin Transactions 2
Issue number2
DOIs
Publication statusPublished - 2002

Fingerprint Dive into the research topics of 'Rearrangement of the 1-oxaspiro[4.5]deca-6,9-dien-8-ylium ion. Part 1. A semiempirical (AM1), density functional and ab initio molecular orbital computational study'. Together they form a unique fingerprint.

  • Cite this