Why are rhodanines less efficient reagents in Diels–Alder reactions than isorhodanines? A quantum chemical study

@article{Tejchman2019WhyAR,
  title={Why are rhodanines less efficient reagents in Diels–Alder reactions than isorhodanines? A quantum chemical study},
  author={Waldemar Tejchman and Michal Michalski and Krzysztof K. Zborowski and Slawomir Berski},
  journal={Journal of Molecular Modeling},
  year={2019},
  volume={25},
  pages={1-11}
}
The reactivity of the 5-arylidenerhodanine and 5-arylideneisorhodanine derivatives in reactions with dimethyl maleate was computationally studied at the DFT(M06-2X)/6–311+G(d,p) theory level. Eight stereoisomers of the reaction products were considered. The effect of the solvent was taken into account by means of the continuous and discrete models for acetic acid (PCM and three CH3COOH molecules). Aromatic stabilization of the transition states was documented by the values of HOMA, NICS(0), and… CONTINUE READING

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