Hydrogen-Bond Acceptance of Solvents: A 19F Solvatomagnetic β1 Database to Replace Solvatochromic and Solvatovibrational Scales
Author(s) -
Christian Laurence,
Sergui Mansour,
Daniela Vuluga,
Aurélien Planchat,
Julien Legros
Publication year - 2021
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c02964
Subject(s) - solvatochromism , chemistry , database , hydrogen bond , hydrogen , organic chemistry , solvent , molecule , computer science
A variety of physicochemical properties and several hydrogen-bond donors have been used to define methods and to build scales aiming at measuring the hydrogen-bond acceptance of solvents. There is a great deal of confusion in these scales and methods. Solvatochromic, solvatocalorimetric, solvatovibrational, and 19 F solvatomagnetic comparison methods are critically reviewed. Only two methods, the solvatomagnetic and the solvatocalorimetric ones, are able to yield reliable solvent hydrogen-bond acceptance scales. The solvatomagnetic β 1 scale defined from the 19 F chemical shift of 4-fluorophenol is extended to many solvents including ionic liquids and green solvents. The results for about 240 hydrogen-bond acceptor solvents are organized in a numerical β 1 database. The comparison of β 1 with solvatochromic scales highlights their shortcomings, in particular for the important class of amphiprotic solvents. Therefore, the use of the 19 F solvatomagnetic comparison method and of the solvatomagnetic β 1 scale is recommended in solvent effect studies.
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