Involvement of organic fluorine substitution in the crystalline packing structures of tricyclic Diels-Alder adducts derived from diarylfulvenes and N-arylimides

Anke Schwarzer, Petra Bombicz, Edwin Weber

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Fluorinated tricyclic Diels-Alder adducts derived from corresponding diarylfulvenes and N-arylmaleimides, each of different degree and positions of the fluorine substituents, and including the non-fluorinated parent compound, have been synthesized. Their X-ray crystal structures were determined in order to study the effect of fluorine substitution on the solid state organization in competition with other weak intermolecular interactions. A balanced interplay of C-H⋯O, C-H⋯F and especially C-H⋯π contacts is typical of the crystal packings while other potential interactions such as C-F⋯F, C-F⋯πF, πH⋯πF and Br⋯Br are secondary or not to be found. Isostructurality calculations and comparison of molecular conformations have been performed in order to structurally classify the compounds depending on the number and mode of fluorination.

Original languageEnglish
Pages (from-to)345-356
Number of pages12
JournalJournal of Fluorine Chemistry
Volume131
Issue number3
DOIs
Publication statusPublished - Mar 1 2010

Keywords

  • Fluorinated Diels-Alder adducts
  • Fluorine involved contacts
  • Isostructurality calculations
  • Supramolecular interactions
  • X-ray crystal structures

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Involvement of organic fluorine substitution in the crystalline packing structures of tricyclic Diels-Alder adducts derived from diarylfulvenes and N-arylimides'. Together they form a unique fingerprint.

  • Cite this