[orgo814]

I'm looking at a problem that deals with the interaction between chloroform and benzene.

The favored geometry is the ailment of the hydrogen of chloroform with the quadrupole of benzene. It says a less favored reaction is with the chlorines interacting with the "edge region" of benzene since the "interaction of partial charges of both partners are more diffuse". What do they mean? How is it more diffuse? The partial positive is on the hydrogen which doesn't undergo resonance unlike the negative region...

[orgopete]

I think in this case, they mean it is weaker. The edge protons of benzene are not as acidic as chloroform. Chlorine atoms are not very basic. Think of how weakly basic chloride must be in HCl.