“…Like the group 14 cations, there is a decrease in aromaticity down the group from the moderately aromatic phosphorenylium cation (ASE = +16.4 kcal mol À1 ) to the weakly aromatic C 2 H 2 As + (+7.5 kcal mol À1 ) and C 2 H 2 Sb + (+3.7 kcal mol À1 ) cations. The value determined here for the aromatic stabilization of the phosphorenylium ion is significantly less than those calculated previously by homodesmotic reactions [Eisfeld and Regitz: 38.4 kcal mol À1 at G2; Gupta and Bansal: 28.9 kcal mol À1 at B3LYP/6-31 + G(d)], [49,50] due to common problems in such determinations including inconsistent ring strain and failure to balance the number of hyperconjugative interactions (Schemes 1 and 2). [13][14][15] Nevertheless, the C 2 H 2 P + cation is calculated to F I G U R E 1 Monoheterocyclic three-membered rings investigated for aromatic or antiaromatic properties T A B L E 3 Calculated NBO-ASE (kcal mol À1 , at M06-2X/ def2-TZVP) and NICS(0) π,zz (ppm, at M06-L/def2-TZVP) for planar three-membered rings C 2 H 2 X (X = CH + , SiH + , GeH + , SnH + , P + , As + , Sb + , Cl + , Br + , I + , S, Se, or Te)…”