Dipole moment analysis of 4H-pyran-4-one and 9H-xanthen-9-one, and their sulphur ana logues, and of 9H-selenoxanthen-9-one, enables a discussion on their aromaticities. In the present work, the dipole moments of tetrahydro-4H-pyran-4-one, tetrahydrothio-4H-pyran-4-one, tetrahydroseleno-4H-pyran-4-one, 9(10H)-anthracen-9-one, 9H-xanthen-9-one, 9H-thioxanthen-9-one and 9H-selenoxanthen-9-one were measured in benzene solution at 30.0 °C.
The electric dipole moment of 5‐(p‐tolyl)tetrazole in dioxane at 30.0° (4.99 D) suggests that the compound is a mixture of the 1H‐tautomer (60 ± 10%) and the 2H‐tautomer (40 ± 10%) in this medium. This determination was made by taking μ (2H) as μ (2Me) = 2.41 D in benzene, and by taking μ (1H) as μ (1Me) = 6.03 D in benzene with due allowance being made for the presence of interannular conjugation in the 1H‐tautomer but not in the 1‐methyl isomer. The dipole moments of 1‐methyl‐5‐(p‐tolyl)tetrazole and 2‐methyl‐5‐(p‐tolyl)tetrazole were also measured in dioxane; that of 1,5‐trimethylenetetrazole was measured in benzene. Comparison with relevant data for unsubstituted tetrazole has also been made.
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