Solvation effects on the relative basicity of propylamines

Abstract

Slight structural molecular variations are known to affect different properties of compounds. In solution, different solute-solvent interactions are known also to alter the properties of numerous compounds. Quantitative structure-activity relationships (QSAR) are used regularly to analyze and predict the variations of different properties of compounds that are caused by structural variations and significant solute-solvent interactions. The relative basicities of n-propylamine, dipropylamine and tripropylamine were determined in nine different solvents from potentiometric titrations. QSAR that were developed from these experimental basicity values were used to evaluate the type and significance of the solute-solvent interactions. The important interactions that influence basicity variations for the propylamines studied are dipolarity-polarizability interaction between the solute and the solvent and hydrogen bonds from the propylammonium ions to basic solvents. The role of hydrogen bonds from the propylamines to acidic solvents is minor.

S N Ar Reactions of Amines in Aprotic Solvents

“…The term quantitative structure property relationship (QSPR) has been recently proposed for cases where a specific property, such as the basicity, is examined 97 .…”

“…The multiparametric equation 14 has been also applied to estimate solvent effects on the relative basicities υG of propylamines 97 :…”

Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents

“…In eqn. (3), K = [B : B]/[B 0 ] 2 stands for the amine autoassociation constant, which is known to be low [12][13][14][15][16] and justifies application of the rate law given by eqn. (3) to the mechanism suggested.…”

Kinetics of the Reaction of 2‐Chloro‐3,5‐dinitrobenzotriflouride with Aniline in Toluene and Methanol‐Toluene Mixed Solvents

“…[12][13][14][15] Most studies of the solvent effects have been performed in pure solvents. [16,17] Nevertheless, different studies aimed at the characterization of mixed solvents and the determination of the kinetic data in binary mixtures. [17] In continuation to the previous work carried out in our laboratory in the field of aromatic nucleophilic substitutions, [19][20][21][22][23][24][25][26][27] the present work investigates the solvent effect on the reaction of 2-chloro-3,5-dinitrobenzotriflouride with aniline in pure toluene, benzene, chloroform and in mixed toluene-methanol.…”