σ-antiaromaticity in cyclobutane, cubane, and other molecules with saturated four-membered rings

Damian Moran, Mariappan Manoharan, Thomas Heine, Paul Von Ragué Schleyer

Research output: Contribution to journalArticle

92 Citations (Scopus)

Abstract

(Figure presented) Dissected nucleus-independent chemical shift (NICS) analyses of cycloalkanes and cage hydrocarbons reveal contrasting ring current effects, diatropic in three- and five-membered and paratropic in four-membered ring systems. The large shielding effects of the C-C bonds of the archetypal σ-aromatic, cyclopropane, are magnified in tetrahedrane and related structures. The remarkable deshielding effect of the cyclobutane C-C(σ) bonds is general: cubane and cages with four-membered rings are strongly deshielding (i.e., σ-antiaromatic).

Original languageEnglish
Pages (from-to)23-26
Number of pages4
JournalOrganic Letters
Volume5
Issue number1
DOIs
Publication statusPublished - 2003 Jan 9

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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