P. Bhyrappa et al., STRUCTURE OF NONPLANAR OCTABROMOTETRAPHENYL PORPHYRIN AND KINETICS OFRAPID METALATION REACTIONS, Chemistry Letters, (5), 1993, pp. 869-872
Octabromotetraphenylporphyrin adopts a severe saddle-shaped distorted
structure owing to the steric crowding of heavy bromine substituents.
The rate enhancement of porphyrin metalation reaction is primarily due
to the nonplanarity of the ring while the electronic effect diminishe
s the affinity of the porphyrin towards metal ions.