Attractive Interaction Caused by the Linear F···Se−C Alignment in Naphthalene Peri Positions

The X-ray crystallographic analysis of 8-fluoro-1-( p -anisylselanyl)naphthalene ( 1 ) revealed that the F and Se atoms and the ipso -carbon of the 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) Å and the FSeC(An) angle was 175.0(1)°. Ab initio MO calculations with the 6-311++G(3df,2pd) basis sets performed on the model compound of 1, HF···SeH 2, where the aryl groups of 1 were replaced by hydrogens. The calculations exhibited that the energy minimum was achieved when the F, Se, and C(An) atoms aligned linearly. Charge transfer in the formation of HF···SeH 2 was suggested to occur from F to SeH 2 on the basis of natural population analysis, which supported the n p x (F)−σ*(Se−C(An)) interaction.