ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The radical anion of 1,1,2.2,9,9,10, 10-octafluoro[2.2]paracyclophane (1) has been generated by electrolytic reduction of 1 in 1,2-dimethoxyethane (tetrabutylammonium perchlorate as the supporting salt). The hyperfine coupling constants of the eight 19F-nuclei and the eight protons, af = 3.35 and aH ≈ 0.10 mT, are qualitatively reproduced by INDO. calculations. According to these calculations, the singly occupied orbital of 1⊖ can be represented by an Ag-combination of two ‘symmetric’ benzene LUMO's, with a substantial transfer of spin population into the 2s-AO's of the F-atoms. Line-width alternation in the ESR. spectrum of 1⊖ indicates an ion pairing of the radical anion with its counter-ion Bu4N⊖. The energy barrier to the migration of the cation between two equivalent sites at the radical anion is determined as 14±2 kJ/mol.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19820650213
