A theoretical analysis of the structure, aromaticity, magnetic properties and bonding in TBSPBOH and SPBOH complexes was performed. Geometry optimizations were carried out in the gas-phase at the B3LYP/6-31G(d) theory level. 1 H and 13 C NMR spectra of these complexes were evaluated at the B3LYP/6-311+G(2d,p)-PCM theory level in CHCl 3 solution. The vector field induced by an external magnetic field was computed at the CHF/6-31G(d) theory level using the CTOCD-DZ formulation. In these cone-shaped molecules, the 14-π electron current induced in them by an external magnetic field does not follow a [14]-annulene path but the inner edge of the macrocycle. Therefore, the 14-π electron aromatic core corresponding to this induced current is constituted by the three meso C atoms, the three N atoms, and the six C atoms directly bonded to them. The involvement of the N atoms in the 14-π aromatic core implies that one of the B - N bonds is a weaker B←N dative bond whose presence is reflected in the geometry of these complexes, which display larger average B - N bond lengths than in tripyrrolylborane. Thus, according to our analysis, structure, aromaticity and bonding in these systems are closely related. The anisotropic effect is somewhat larger in SPBOH than in TBSPBOH, and the larger curvature of the former makes larger relative shielding constants possible, not only for the hydroxyl proton but also for the outer atoms.