An extremely bulky p-terphenyl bis(aniline), p-C 6 H 4 {C 6 H 4 [N(H)TCHP]-2} 2 (TCHP = 2,4,6-tricyclohexylphenyl) TCHP TerphH 2 , has been developed. Deprotonation of a less bulky analogue, Dip TerphH 2 (Dip = 2,6-diisopropylphenyl), with BePh 2 affords the bimetallic system, [(BePh) 2 (μ-Dip Terph)] 1. Treating either TCHP TerphH 2 or Dip TerphH 2 with Mg-{CH 2 (SiMe 3 )} 2 gives the monomeric bis(anilide) complexes [Mg( Ar Terph)] (Ar = Dip 2, TCHP 3) which display rare examples of η 6 -arene coordination to the metal center. Treating 2 with THF leads to partial dissociation of the Mg•••arene interaction and formation of [Mg( Dip Terph)(THF)] 4. Reactions of the bis-(aniline)s with the group 2 metal amides [M{N(SiMe 3 ) 2 } 2 ] afford dimeric, structurally analogous compounds [{M( Ar Terph)} 2 ] (Ar = Dip, M = Ca 5, Sr 6, Ba 7; Ar = TCHP, M = Ca 8, Sr 9, Ba 10) which display intermolecular M•••arene interactions in the solid state. Computational studies have shown that the intramolecular M•••η 6 −arene interactions in models of the ether-free metal bis(anilide) compounds are largely electrostatic in nature. Reductions of these compounds with alkali metals led to mixtures of unidentified products.