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sigma-delocalized radical cations (H(CH/sub 2/)/sub n/H)/sup +/ of primary alkanes: ESR evidence

Journal Article · · J. Phys. Chem.; (United States)
DOI:https://doi.org/10.1021/j150615a001· OSTI ID:6127274
This paper describes the first clear evidence that n-alkane cations (H(CH/sub 2/)/sub n/H)/sup +/ with extended structures are characterized as delocalized sigma radicals. The unpaired electron in the in-plane sigma molecular orbital delocalizes over the entire chain, giving the characteristic 1:2:1 three-line ESR spectra due to the strong hyperfine couplings with the two in-plane end protons. The weak couplings with the out-of-plane CH/sub 2/ protons are unresolvable for most of the cations as is expected from the unpaired electron in the in-plane orbital. The major hyperfine couplings with the in-plane protons decrease with increasing carbon number from 152 G for C/sub 2/H/sub 6//sup +/ to 16 G for n-C/sub 10/H/sub 22//sup +/ depending upon the sigma delocalization over the extended chain. The coupling values obtained from the INDO calculations using standard geometry are in good agreement with the observation, although a slight tilt of the CH/sub 3/ axis was required for the lower alkane cations with n less than or equal to 4.
Research Organization:
Government Industrial Research Inst., Nagoya, Japan
OSTI ID:
6127274
Journal Information:
J. Phys. Chem.; (United States), Journal Name: J. Phys. Chem.; (United States) Vol. 85:15; ISSN JPCHA
Country of Publication:
United States
Language:
English