Science China Chemistry

, Volume 58, Issue 12, pp 1845–1852

Comparative study on the methods for predicting the reactive site of nucleophilic reaction

Articles

DOI: 10.1007/s11426-015-5494-7

Cite this article as:
Cao, J., Ren, Q., Chen, F. et al. Sci. China Chem. (2015) 58: 1845. doi:10.1007/s11426-015-5494-7

Abstract

Predicting the reactivity of nucleophilic reaction at different sites has important theoretical and practical significance. Many prediction methods solely based on the electronic structure of reactants have been proposed. In this paper, detailed comparative analyses on the reliability of 14 methods are carried out and three series of molecules, carbonyl compounds, aromatic hydrocarbons and pyridine derivatives are exploited as test systems. It is found that the methods reflecting local electronic softness, such as condensed dual descriptor, have satisfactory prediction ability; while the ones reflecting electrostatic effect, such as atomic charge analysis and electrostatic potential analysis, have evidently worse overall performance. For all systems of interest, condensed dual descriptor and Hirshfeld charge display the most robust predictive capacity.

Keywords

nucleophilic reaction molecular surface Fukui function dual descriptor electrostatic potential atomic charge orbital composition relative electrophilicity 

Copyright information

© Science China Press and Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  1. 1.Department of Chemistry and Chemical Engineering, School of Chemical and Biological EngineeringUniversity of Science and Technology BeijingBeijingChina
  2. 2.Beijing Kein Research Center for Natural SciencesBeijingChina