14-Methyl-, 14-chloro-, 14-fluoro-retinals have been incorporated into
apo-retinochrome to investigate the effect of the electronegativities
of C-14 substituents on the protonation of the Schiff base. The exten
t of protonation decreased in going from 14-methyl- to 14-chloro- to 1
4-fluoro-retinal. There was usually no protonation in the case of the
14-fluoro analogue. The chromophore-protein interactions are also disc
ussed.