Electronic structure and conformational properties of the amide linkage
1989; Elsevier BV; Volume: 192; Issue: 1-2 Linguagem: Inglês
10.1016/0022-2860(89)87013-9
ISSN1872-8014
AutoresM. Woydt, Paul Rademacher, Gerd Kaupp, O. Sauerland,
Tópico(s)Chemical synthesis and pharmacological studies
ResumoThe photoelectron spectra of N-vinyllactams 4–6 have been obtained. Based on band shape analyses and AM1 calculations the ionization potentials are assigned to molecular orbitals. The sequence of the three highest occupied MOs was found to be: π3 (HOMO), nO, π2. The MOs π3 and π2 are essentially linear combinations of πN and πCC. Some conformational properties of N-vinyllactams have been studied by AM1 calculations on N-methyl-N-vinylacetamide (1) as a model compound for torsions of the vinyl and the acetyl group. Planar forms (ap and sp) were found as stable conformers. For 3–6 AM1 calculations also revealed essentially planar vinyllactam units, while the α-lactam derivative 2 has a pyramidal nitrogen atom.
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