W0082

The Structural Chemistry of Some Synthetically Important Intranmolecularly Stabilized Organochalcogenyl Halides REX (R = benzyl, naphthyl; E = S, Se, Te; X = Cl, Br, I). Ray J. Butcher, Department of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA, H. B. Singh, G. Mugesh, A. Panda, Department of Chemistry, Indian Institute of Technology, Bombay, India

Although the versatility of areneselenenyl halides is well recognized in selective organic symthesis, the precise structural properties around the selenium have not been well determined. In the solid state and in solution it has been frequently found that the divalent selenium further interacts with nearby heteroatoms (O, N, etc.,) forming a pseudo high-valent selenium species. In particular, the nature of an Se...N interaction is of great interest in connection with the catalytic mechanism of a selenium containing anti-oxidant enzyme, glutathione peroxidase. The structures of a series of organochalcogenyl halides REX (R = benzyl, naphthyl; E = S, Se, Te; X = Cl, Br, I) have been determined. Both chiral and achiral derivatives have been obtained. Depending on the nature of R, E, and X an intramolecular interaction between E and the adjacent heteroatom (N) is obtained which ranges in strength from an E-N single covalent bond to a weak non-bonding interaction. Factors which determine the strength of this intramolecular interaction will be discussed.