Abstract
The dipole moments of fourteen m-dinitrobenzenes with different substituents (OMe, CN, CH 3, CHO, Cl, CF 3, COOMe, F, Br, NH 2) in various positions were measured in order to study mesomeric interactions. Inclusion of conformational considerations permitted estimates to be made for the mesomeric moments of these groups at given positions. The values obtained could be applied with consistent results to a total of forty m-dinitrobenzenes, including others previously reported. The mesomeric moment increments deduced, compared with substituted benzenes possessing no nitro groups, were found to be only slightly larger than in non-nitro substituted benzenes (compared with substituted alkanes), which would indicate a reluctance of the extended π system of m-dinitrobenzene to interact with other substituents present, in any way other than by direct extension of the π network. One apparent case of intermolecular electron donor-acceptor complex formation was detected. The measured dipole moment of o-iodoanisole indicates a planar anti conformation for the methoxyl group.
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