Substituent effects
The ability to fine-tune pi stacking interactions would be useful in numerous synthetic efforts. One example would be to increase the binding affinity of a small-molecule inhibitor to an enzyme pocket containing aromatic residues. The effects of heteroatoms and substituents on pi stacking interactions is difficult to model and a matter of debate.
- Huber RG, Margreiter MA, Fuchs JE, von Grafenstein S, Tautermann CS, Liedl KR, Fox T (May 2014). “Heteroaromatic π-stacking energy landscapes”. Journal of Chemical Information and Modeling. 54 (5): 1371–1379. doi:10.1021/ci500183u. PMC 4037317. PMID 24773380.
