Abstract
THE electric dipole moments of the α- and β- salicylides (assumed to be disalicylides) were found to be 6.27 and 2.42 D. respectively in benzene solution. The solutions showed no change of polarization with time. The former, being definitely a disalicylide, may therefore be given the cis configuration (cf. Iβ above). Baker, Banks, Lyon and Mann1 have shown that the geometry of this form of ring is variable, but the configuration (Iβ) is the most likely because the resonance energy will then be a maximum (cf. Marsden and Sutton2). The moment of the compound should then be approximately the resultant of the two lactone group moments (each of 4·12 D.2) at an angle θ, which can be calculated if the angles φ and ρ are known (see diagram). The angles Ph—C—O and Ph—O—C may each be assumed to lie between the limits of 109·5° and 120°. Since the rest of the geometry of the molecule is determined by the benzene rings, φ = 64·5—70middot;5°. ρ may be obtained from a molecular-orbital calculation3 and is found to be c. 27°. θ is therefore 82—86°, and the calculated moment is 6·2—6·0 D.
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Baker, W., Banks, R., Lyon, D. R., and Mann, F. G., J. Chem. Soc., 28 (1945).
Marsden, R. J. B., and Sutton, L. E., J. Chem. Soc., 1383 (1936).
Orgel, L. E., private communication.
Coop, I. E., and Sutton, L. E., J. Chem. Soc., 1269 (1938).
Davidson, N. R., and Sutton, L. E., J. Chem. Soc., 347 (1939).
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EDGERLEY, P., SUTTON, L. Dipole Moments of the Salicylides. Nature 164, 1050 (1949). https://doi.org/10.1038/1641050a0
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DOI: https://doi.org/10.1038/1641050a0
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