3-(1-NAPHTHYLOXY)-1,2-BENZISOTHIAZOLE 1,1-DIOXIDE - ELECTRONIC EFFECTS OF CONJUGATION

The conjugation of oxygen with an aromatic ring, as in 1-naphthol, res ults in a C-O bond length of 1.35 Angstrom and a C-O-C bond angle of a lmost 120 degrees, whereas the C-O bond length in an aliphatic ether i s about 1.45 Angstrom, with a C-O-C angle of about 110 degrees. The ps eudo-saccharyl ether of 1-naphthol, C17H11NO3S, changes the phenolic C -O bond length to 1.422(7) Angstrom, while maintaining the C-O-C angle . The result implies that the original naphtholic O atom is no longer pi-conjugated with the naphthalene ring system, but only with the sacc haryl system.