Journal
SCIENCE CHINA-CHEMISTRY
Volume 58, Issue 12, Pages 1845-1852Publisher
SCIENCE PRESS
DOI: 10.1007/s11426-015-5494-7
Keywords
nucleophilic reaction; molecular surface; Fukui function; dual descriptor; electrostatic potential; atomic charge; orbital composition; relative electrophilicity
Categories
Funding
- National Natural Science Foundation of China [21173020, 21473008]
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available