Abstract
Since chloro and methyl groups have nearly the same volume, they may be interchanged in a molecule without altering the crystal structure. Such isostructural behaviour is found when crystal stabilization is mainly through dispersive and repulsive interactions. Violations of this rule are, however, observed when directional forces or weak bonds are involved and the failure of complete chloro-methyl exchange in a substance like hexachlorobenzene, points to the importance of weakly attractive Cl...Cl interactions.
Similar content being viewed by others
References
Desiraju G R 1984Endeavour 8 201
Jones W, Ramdas S, Theocharis C R, Thomas J M and Thomas N W 1981J. Phys. Chem. 85 2594
Jones W, Theocharis C R, Thomas J M and Desiraju G R 1983J. Chem. Soc., Chem. Commun. 1443
Kitaigorodskii A I 1973 ‘Molecular crystals and molecules’ (New York: Academic Press)
Sarma J A R P and Desiraju G R 1985Chem. Phys. Lett. 117 160
Simonetta M 1974Acc. Chem. Res. 7 345
Theocharis C R, Desiraju G R and Jones W 1984J. Am. Chem. Soc. 106 3606
Thomas J M 1974Philos. Trans. R. Soc. London A277 251
Williams D E and Hsu L-Y 1985Acta Cryst. A41 296
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Desiraju, G.R., Sarma, J.A.R.P. The chloro-methyl exchange rule and its violations in the packing of organic molecular solids. Proc. Indian Acad. Sci. (Chem. Sci.) 96, 599–605 (1986). https://doi.org/10.1007/BF02936309
Issue Date:
DOI: https://doi.org/10.1007/BF02936309