Journal
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Volume 26, Issue 3, Pages 280-285Publisher
WILEY-BLACKWELL
DOI: 10.1002/poc.3083
Keywords
solvatochromism; solvent dipolarity; solvent polarizability; 2-(N; N-dimethylamino-7-nitrofluorene; -carotene; ionic liquids; 2-alkoxyethanols; carboxylic acid esters; acid anhydrides
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Funding
- FAPESP (State of Sao Paulo Research Foundation)
- National Council for Scientific and Technological Research (CNPq)
- Academy of Sciences for the Developing World, (TWAS)
- Petrobras S. A.
- CAPES
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The effects of solvents on chemical phenomena (rate and equilibrium constants, spectroscopic transitions, etc.) are conveniently described by solvation free-energy relationships that take into account solvent acidity, basicity and dipolarity/polarizability. The latter can be separated into its components by manipulating the UVvis spectra of two solvatochromic probes, 2-(N,N-dimethylamino)-7-nitrofluorene (DMANF) and a di-(tert-butyl)-tetramethyl docosanonaen probe (ttbP9) whose synthesis is laborious and expensive. Recently, we have shown that the natural dye -carotene can be conveniently employed instead of ttbP9 for the determination of solvent polarizability (SP) of 76 molecular solvents and four ionic liquids. In the present work, we report the polarizabilities of further 24 solvents. Based on the solvatochromism of -carotene and DMANF, we have calculated solvent dipolarity (SD) for 103 protic and aprotic molecular solvents, and ionic liquids. The dependence of SD and SP on the number of carbon atoms in the acyl- or alkyl group of several homologous series (alcohols; 2-alkoxyethanols; carboxylic acid- anhydrides, and esters, ionic liquids) is calculated and briefly discussed. Copyright (c) 2013 John Wiley & Sons, Ltd.
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