Electric moments and conformation of substituted fluoroformates in benzene solutions

Abstract
The dipole moments of methyl-, ethyl-, n-propyl-, n-butyl-, n-amyl-, and phenyl-fluoroformate were determined in dilute benzene solutions at 25 °C. The experimental results suggest that the conformation of the fiuoro-esters is similar to the conformation of the chloro-esters and differs from the conformation of the normal esters; viz. the ester hydrocarbon group and the fluorine atom are cis to each other. Results of fluorine and proton n.m.r. measurements on these molecules support the conclusions based on the dipole moment data if a "through-space" coupling mechanism is assumed for the long range spin–spin coupling JH–F1−5.

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