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Empirical Treatment of the Inductive and Dispersive Components of Solute−Solvent Interactions: The Solvent Polarizability (SP) Scale
Author(s) -
Catalán Javier,
Hopf Henning
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400311
Subject(s) - polarizability , solvatochromism , chemistry , solvent , chromophore , anthracene , solvent effects , carbon disulfide , computational chemistry , chemical physics , photochemistry , organic chemistry , molecule
By using 3,20‐di‐ tert ‐butyl‐2,2,21,21‐tetramethyl‐3,5,7,9,11, 13,15,17,19‐docosanonaene (ttbP9) as a probe, the inductive and dispersive interactions of solvents were empirically evaluated for the first time. This probe exhibits a very strong first electronic transition with a marked vibronic structure that is very well resolved from the second electronic transition. One hundred solvents were used to construct a solvent polarizability (SP) scale ranging from zero for the gas phase (i.e. the absence of solvent) to unity for carbon disulfide. The probe was found to exhibit an ideal spectroscopic behaviour towards a variety of polar, acidic and basic solvents. The polarizability scale provides an accurate description of the solvatochromism of such interesting apolar chromophores as anthracene, molecular oxygen, and C 60 among a wider variety of solvents spanning very broad ranges of polarity, acidity and basicity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)