Issue 52, 2020, Issue in Progress

Theoretical investigation on the nature of 4-substituted Hantzsch esters as alkylation agents

Abstract

Recently, a variety of 4-substituted Hantzsch esters (XRH) with different structures have been widely researched as alkylation reagents in chemical reactions, and the key step of the chemical process is the elementary step of XRH˙+ releasing R˙. The purpose of this work is to investigate the essential factors which determine whether or not an XRH is a great alkylation reagent using density functional theory (DFT). This study shows that the ability of an XRH acting as an alkylation reagent can be reasonably estimated by its ΔGRD(XRH˙+) value, which can be conveniently obtained through DFT computations. Moreover, the data also show that ΔGRD(XRH˙+) has no simple correlation with the structural features of XRH, including the electronegativity of the R substituent group and the magnitude of steric resistance; therefore, it is difficult to judge whether an XRH can provide R˙ solely by experience. Thus, these results are helpful for chemists to design 4-substituted Hantzsch esters (XRH) with novel structures and to guide the application of XRH as a free radical precursor in organic synthesis.

Graphical abstract: Theoretical investigation on the nature of 4-substituted Hantzsch esters as alkylation agents

Article information

Article type
Paper
Submitted
05 Aug 2020
Accepted
20 Aug 2020
First published
25 Aug 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 31425-31434

Theoretical investigation on the nature of 4-substituted Hantzsch esters as alkylation agents

G. Shen, L. Xie, H. Yu, J. Liu, Y. Fu and M. Yan, RSC Adv., 2020, 10, 31425 DOI: 10.1039/D0RA06745H

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