%0 Journal Article
%A Gao, Fang
%A Boyles, David
%A Sullivan, Rodney
%A Compton, Robert N.
%A Pagni, Richard M.
%D 2002
%T Photochemistry of Racemic and Resolved 2-Iodooctane. Effect of
Solvent Polarity and Viscosity on the Chemistry
%U https://acs.figshare.com/articles/journal_contribution/Photochemistry_of_Racemic_and_Resolved_2-Iodooctane_Effect_of_Solvent_Polarity_and_Viscosity_on_the_Chemistry/3693960
%R 10.1021/jo020472r.s001
%2 https://ndownloader.figshare.com/files/5784318
%K IP
%K media
%K methanol
%K racemic
%K iodooctane
%K methyl
%K cyclopentane
%K RP
%K photochemistry
%K substrate
%K gas phase
%X The photochemistry of racemic and resolved 2-iodooctane was examined in cyclopentane, methanol,
and 2-methyl-2-propanol, media with differing polarities and viscosities. The photochemistry of
racemic 2-iodooctane was also examined in the gas phase. The photochemistry of 2-deuterio- and
1,1,1-trideuterio-2-iodooctane in cyclopentane and methanol was also studied. The photoreactions
in cyclopentane, 2-methyl-2-propanol, and the gas phase occurred exclusively through homolytic
reactions, while in methanol, they occurred predominantly (>53%) through heterolytic reactions.
By comparing the disappearance of the optically active substrate with its loss of optical activity, F,
the fraction of the initially formed radical pair (RP) or ion pair (IP) resulting in product was
determined for the three solvents. Because F contains contributions of both escape of the partners
in the RP or IP into the bulk of the solvent and reaction within the RP or IP to yield products other
than the substrate, there was no correlation between F and solvent viscosity. The F values will be
valuable in assessing the photochemistry of 2-iodooctane in the same media with circularly polarized
light.
%I ACS Publications