Abstract
The photoelectron and IR spectra of a number of sulfenamide derivatives and their H-complexes have been investigated, A correlation between an increase in the vertical ionization potential of the lone electron pair of the nitrogen atom and a decrease in the frequency shift of the stretching OH-vibrations in the H-complexes of compounds R3N, R2NCH2OR, R2NSR, and R2NSOR was found. The electronic and geometric structures of the starting bases and their H-complexes were calculated by theab initio and MNDO methods. Anomeric interactions were found to decrease the energy of the n(N) orbital and to hinder the formation of H-complexes. The calculations of the sulfenamides and their H-complexes in unstable conformations, characterized by increased energies of H-complexation and proton affinity, were also carried out.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2894–2897, December, 1996.
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Zverev, V.V., Titova, Z.S. Theoretical and experimental investigation of stereoelectronic interactions in H-complexes of sulfenamide derivatives. Russ Chem Bull 45, 2745–2748 (1996). https://doi.org/10.1007/BF01430634
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DOI: https://doi.org/10.1007/BF01430634