The formation of macrocycles containing two imidazolium rings such as 1·2X and 2·2X is anion-directed through hydrogen bonding. The template effect exerted by the chloride anion in the ring-closure reaction of the monocationic model intermediate 9+ to yield the [14]imidazoliophane 22+has been evaluated. This effect was quantified following the kinetics of the macrocyclization byusing a UV−vis technique. The rate of the ring closure of monocation 9+ is increased up to 10times, in the presence of Bu4NCl 0.04 M. This finding confirms that the template effect is operativein the macrocyclization leading to dicationic [14]imidazoliophanes.