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, results in a C—O bond length of 1.35 Å and a C—O—C bond angle of almost 120°, whereas the C—O bond length in an aliphatic ether is about 1.45 Å, with a C—O—C angle of about 110°. The pseudo-saccharyl ether of 1-naphthol, C₁₇H₁₁NO₃S, changes the phenolic C—O bond length to 1.422 (7) Å, while maintaining the C—O—C angle. The result implies that the original naphtholic O atom is no longer π-conjugated with the naphthalene ring system, but only with the saccharyl system.

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