Abstract
4,4′‐Bis(dimethylamino)benzophenone (Michler's Ketone) — a Common Indicator of the Acidity and Dipolarity/Polarizability of Reaction MediaThe solvatochromisms of Michler's Ketone (1) and the iron (II) complex Fe(phen)2(CN)2 (2) has been investigated in 73 solvents of different polarity. The solvent‐induced UV/Vis‐absorption shifts of 1 and 2 are mainly attributed to both the hydrogen‐bond donor acidity and dipolarity/polarizability of the solvent as verified by a Kamlet‐Taft correlation analysis and comparison with common solvent‐polarity scales such as Reichardt's ET(30) values and the acceptor scale of Gutmann. Michler's Ketone exhibits the largest positive solvatochromism known so far. The specific role of phenolic solvents has been discussed with regard to a charge‐transfer complexation between the positively polarized ring of 1, caused by the hydrogen‐bond formation at the carbonyl oxygen, and the aromatic ring of the phenol.
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