Journal of Molecular Structure p. 239 - 252 (1981)
Update date:2022-08-18
Topics:
Lumbroso, H.
Liegeois, Ch.
Devillanova, F. A.
Verani, G.
The electric dipole moments in benzene and dioxan of potentially tautomerizable N-methylimidazolidin-2-one, N-methylimidazolidine-2-thione and -2-selenone clearly support the lactam structure for these compounds.The fact that their dipole moments in dioxan are markedly greater than those in benzene is explained by a higher (HN-C=Y) mesomeric moment in the hydrogen-bonded solute...dioxan complexes.Analysis of the dipole moments in benzene of N,N'-dimethylimidazolidin-2-one, N,N'dimethylimidazolidine-2-thione and -2-selenone shows that the mesomeric moment (due to contribution of +N=C-Y- zwitterionic valence structures) gradually increases on going from Y=O to Y=S, and Y=Se.Finally, preferred conformations, from their dipole moments in benzene, are suggested for tetramethylurea and tetramethylthiourea.
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