ATTRACTIVE INTERACTION CAUSED BY THE LINEAR F-CENTER-DOT-CENTER-DOT-CENTER-DOT-SE-C ALIGNMENT IN NAPHTHALENE PERI POSITIONS

The X-ray crystallographic analysis of 8-fluoro-1-(p-anisylselanyl)nap hthalene (1) revealed that the F and Se atoms and the ipso-carbon of t he p-anisyl group (C(An)) aligned linearly. The F atom and the Se-C(An ) bond lay on the naphthyl plane: the nonbonded distance between F and Se atoms was 2.753(3) Angstrom and the FSeC(An) angle was 175.0(1)deg rees. Ab initio MO calculations with the 6-311++G(3df, 2pd) basis sets performed on the model compound of 1, HF ... SeH2, where the aryl gro ups of 1 were replaced by hydrogens. The calculations exhibited that t he energy minimum was achieved when the F, Se, and C(An) atoms aligned linearly. Charge transfer in the formation of HF ... SeH2 was suggest ed to occur from F to SeH2 on the basis of natural population analysis , which supported the np(x)(F)-sigma(Se-C(An)) interaction.