A DFT Computational and Synthetic Study of New Curcuminoidpropargyl Adducts with Pseudo-Cofacial Aryl Rings
CHEMISTRYSELECT(2022)
Abstract
With the aim to utilize transannular pi-pi interactions as a driving force to assemble cofacial pi-decks, a DFT computational study was performed on the adducts resulting from coupling of curcuminoids (CURs), bearing electron-withdrawing groups (F, CF3, SCF3, OCF3) in the aryl rings, with 1,3-diphenylpropargyl moiety and its p-OMe-substituted derivatives. Detailed analysis of the structural and electronic properties of the resulting assemblies revealed the existence of intermolecular aromatic pi-pi stacking interactions between one pair, and in some cases two pairs, of aryl rings. Structural/ electronic changes resulting from pi-complexation to Ag+ (mono and bis adducts), and to Cr(CO)(3) acting as pi-electron sink, were also examined. Motivated by the DFT computations outcomes, the feasibility to access these adducts via a simple one-pot reaction using bismuth nitrate as catalyst was shown in representative cases, along with complexation to AgOTf via an NMR study.
MoreTranslated text
Key words
Curcuminoids, DFT computations, Model synthesis, Propargyl alcohols Transannular pi-pi interactions
AI Read Science
Must-Reading Tree
Example
![](https://originalfileserver.aminer.cn/sys/aminer/pubs/mrt_preview.jpeg)
Generate MRT to find the research sequence of this paper
Chat Paper
Summary is being generated by the instructions you defined