It is a fact that aromatic molecules in general bind stronger to plasma proteins than more genuinely sp2-hypridized ones. In QSPR models of plasma protein binding, the HOMO energy often has a positive coefficient. Is this because aromatic molecules in general have a higher HOMO energy than non-aromatic, or is it a completely different thing?
To the best of my knowledge, the HOMO lies lower in energy for an aromatic compound than for the corresponding non-aromatic compound. The aromatic stabilization energy (ASE) which contributes to the HOMO is reason for the lowering in energy. ASE is not present in a non-aromatic molecule, thus this lowering in energy is not observed and the HOMO lies higher in energy. (Of course, this counts only, if you look at comparable molecules, e.g. benzene vs. non-aromatic cyclohexatriene)
Dominik! Thank you very much for your rep. This was valuable to me.
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