All-carbon molecules: Evidence for the generation of cyclo[18]carbon from a stable organic precursor

François Diederich, Yves Rubin, Carolyn B. Knobler, Robert L. Whetten, Kenneth E. Schriver, Kendall N. Houk, Yi Li

Research output: Contribution to journalArticlepeer-review

103 Scopus citations

Abstract

The unambiguous structural characterization of a single-sized all-carbon molecule requires its chemical synthesis. For cyclo[18]carbon, ab initio calculations predict a relatively stable, cyclic D9h ground state geometry with alternating C-C (1.36 angstroms) and C≡C (1.20 angstroms) bonds. The synthesis and x-ray crystal structure of a direct precursor to C 18 are described. The analysis of laser flash heating experiments on this precursor by time-of-night mass spectroscopy shows a sequence of retro-Diels-Alder reactions leading to C18 as the predominant fragmentation pattern. Structural evidence is provided for the generation of an all-carbon molecule from a well-characterized organic precursor.

Original languageEnglish (US)
Pages (from-to)1088-1090
Number of pages3
JournalScience
Volume245
Issue number4922
DOIs
StatePublished - 1989
Externally publishedYes

ASJC Scopus subject areas

  • General

Fingerprint

Dive into the research topics of 'All-carbon molecules: Evidence for the generation of cyclo[18]carbon from a stable organic precursor'. Together they form a unique fingerprint.

Cite this