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Partition coefficients and intramolecular hydrogen bonding. 2. The influence of partition solvents on the intramolecular hydrogen-bond stability of salicyclic acid derivatives

✍ Scribed by Michel Berthelot; Christian Laurence; Maryvonne Lucon; Christophe Rossignol; Robert W. Taft

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
406 KB
Volume
9
Category
Article
ISSN
0894-3230

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✦ Synopsis

The intramolecular hydrogen bonding (chelation) of salicylaldehyde, methyl salicylate, N , Ndimethylsalicylamide and 2-hydroxyacetophenone was studied by IR spectroscopy in different phases used for partition coefficient determinations. The extent of chelation was found to be highly sensitive to the solvent and to the substituent on the carbonyl group in the orders carbon tetrachloride = chloroform p. octanol >water 9 dimethyl sulfoxide and OMe = Me > H s NMe,. These sequences are discussed in terms of hydrogen-bond acidity of the hydroxyl group, hydrogen-bond basicity of the carbonyl group, planarity of the solute molecule and hydrogen-bond aciditylbasicity properties of the solvent. Semi-empirical and a6 initio calculations confirmed the substituent sequence.

* For the sake of simplicity, we also use the old term 'chelation' that has been widely used as a synonym of intramolecular hydrogen bonding in salicylic compounds.y

The process ab will be called 'dechelation.'

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