Comparative estimate of p-π interaction in vinyl ethers and sulfides
Vinyl sulfides, when they form a hydrogen bond with phenol, shift the stretching vibrations of the O-H of phenol more strongly than do the vinyl ethers; the reverse relation is observed for the saturated analogs.
A comparison with the data of H-bonding involving the vinyl ethers makes it possible to attribute the observed “inversion” in the basicity as being mainly due to the p-π conjugation in the vinyloxy group.
KeywordsHydrogen Ether Sulfide Phenol Hydrogen Bond
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