Interaction between stacked aryl groups in 1, 8-diarylnaphthalenes: Dominance of polar/π over charge-transfer effects

Abstract

Several 1, 8-diarylnaphthalenes have been prepared, and the barrier to rotation around the aryl/naphthalene bond has been measured. In these molecules steric congestion forces the aryls in a parallel stacked geometry. The barriers to rotation were used to evaluate the strength and to investigate the nature of the interaction between the arenes. The variance of the AG* for the rotation upon arene substitution with electron donating or electron withdrawing groups indicates that polar/π electrostatic effects dominate over charge-transfer effects in determining the arene/arene interaction. © 1995 IUPAC