IN some of their applications, the current generalised theories of benzene substitution discard steric factors too lightly. For the purpose of a priori consideration, it can be assumed that the effective reagent in a substitution does not occupy a smaller volume than the group which is eventually installed in place of hydrogen.
"Atomic Radii", An. Rep. Chem. Soc., p. 402; 1931.
Bradfield and Jones, J. Chem. Soc., 1009; 1928.
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LE FÈVRE, R. Volumes of Alkyl Groups and their Orienting Powers. Nature 131, 655 (1933). https://doi.org/10.1038/131655a0