A dipole moment study of organo-chalcogen compoun |
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Authors: | H. Lumbroso Ch. Liégeois N. Dereu L. Christiaens A. LuXen |
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Affiliation: | Laboratoire de Chimie Générale, Université Pierre et Marie Curie, 4, Place Jussieu, 75230 Paris Cedex 05 France;Institut de Chimie Organique B6, Université de Liège au Sart Tilman, B-4000 LiègeBelgium |
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Abstract: | Analysis of the dipole moments of chalcogenoanisoles, the directions of which are given by those of their p-bromo derivatives, shows that the mesomeric moment decreases on passing from anisole to thioanisole, selenoanisole and telluroanisole (m = 1.1, 0.5, 0.25 and 0.18 D, respectively). In p-nitrochalcogenoanisoles and 1-chalcogenochroman-4-ones the interaction moment follows the reverse order, which is ascribed to the increasing sensitivity of the chalcogen mesomeric moment to the chalcogen atomic number and polarizability. The less-hindered (Te, O)-cis conformation is preferred for 2-acyl-3-methyltellurothiophenes and 3-acyl-2-methyltellurothiophenes (acyl: formyl or acetyl), and 3-formyl-4-methyltellurothiophene. Rotational isomerism in bis(2-furyl), bis(2-thienyl), bis(3-thienyl) and bis(2-selenienyl) ditelluride is also examined, and the dipole moments of 1-chalcogenochroman-4-ones, 2-chalcogenochroman-1-ones and 2-chalco-genochrom-1-ones analyzed. |
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