Quantitative structure–reactivity study on sulfonation of amines, alcohols and phenols

Abstract

Quantitative structure–reactivity relationship (QSRR) can be considered as a variant of quantitative structure property relationship (QSPR) studies, where the chemical reactivity of reactants in a specified chemical reaction is related to chemical structure. As follows, the sulfonation reaction yield of 24 amines, alcohols and phenols with sulfonyl chloride was studied by QSRR. Quantum chemical calculations (b3lyp/6-31+g (d)) were carried out to obtain the optimized geometry. The suitable set of molecular descriptors was calculated to represent the molecular structures of compounds, such as constitutional, topological, geometrical, electrostatic and quantum-chemical descriptors. The genetic algorithm (GA) was applied to select the variables that resulted in the best-fitted models. After the variable selection, multiple linear regression (MLR) was utilized to construct linear QSRR models. The maximum relative error in prediction (5.26) showed that the predictive ability of the model was satisfactory and it can be used for designing similar reactants with efficient sulfonation reaction.

Keywords

• Quantitative structure–reactivity relationship
• Sulfonation reaction
• Quantum chemical calculations
• Synthesis
• Reaction yield