Twisting-based spectroscopic measure of solvent polarity: the P(T) scale

J Org Chem. 2013 Jun 21;78(12):5925-31. doi: 10.1021/jo400586w. Epub 2013 Jun 12.

Abstract

The P(T) scale, which is correlated well with the E(T)(30), Y, and Z scales, is the first twisting-based spectroscopic measure of solvent polarity. It is based on two combined mechanisms: (1) the solvent-dependent intramolecular charge-transfer absorption that displays a regular hypsochromic band shift in polar solvents and (2) overcoming the intramolecular hydrogen-bond of o-1 by its differentiated solvation in polar solvents, causing a C-C bond to twist that leads to a regular hypsochromic shift of its lowest energy electronic absorption band.