Conformational behavior of 3-borabicyclo[3.3.1]nonanes. Intramolecular p-σ and p-π interactions in 3,7-endo-disubstituted 3-borabicyclo[3.3.1]nonanes

Mikhail E. Gurskii, Alexei V. Gueiderikh, Yuri N. Bubnov, Mikhail Yu Antipin, Konstantin A. Lyssenko, Ilya D. Gridnev, Roland Boese, Dieter Blaeser

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Intramolecular interactions between the unoccupied p-orbital of the boron atom and the σ- (Me) or π-orbital (Ph) of the 7-endo-substituent lead to an unusual stability of the chair-chair conformation in 3-borabicyclo[3.3.1]nonanes. X-ray analysis of 3,7α-dimethyl-3-borabicyclo[3.3.1]nonane (7) and 3-methyl-7α-phenyl-3-borabicyclo[3.3.1]nonane (8), and single point ab initio calculation (B3LYP/6-31G*) of 8 have confirmed the existence of this specific attractive interaction.

Original languageEnglish
Pages (from-to)3-6
Number of pages4
JournalJournal of Organometallic Chemistry
Volume636
Issue number1-2
DOIs
Publication statusPublished - 2001 Nov 25
Externally publishedYes

Keywords

  • 3-Borabicyclo[3.3.1]nonanes
  • Conformation analysis
  • P-σ and p-π interactions
  • X-ray analysis

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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