Theoretical investigation on the nature of 4-substituted Hantzsch esters as alkylation agents.
RSC Adv
; 10(52): 31425-31434, 2020 Aug 21.
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| MEDLINE
| ID: mdl-35520635
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 XRHË+ releasing RË. 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 ΔG ≠ RD(XRHË+) value, which can be conveniently obtained through DFT computations. Moreover, the data also show that ΔG ≠ RD(XRHË+) 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 RË 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.
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RSC Adv
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2020
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Article