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Synthesis, Single Crystal X-ray Structure Analysis and Computational Electronic Structure Investigations of 2-amino-7,7-dimethyl-4-(4-(methylthio)phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

  • Ali RamazaniEmail author
  • Hamideh AhankarEmail author
  • Katarzyna Ślepokura
  • Tadeusz Lis
  • Pegah Azimzadeh Asiabi
  • Masoome Sheikhi
  • Farideh Gouranlou
  • Hooriye Yahyaei
Original Paper

Abstract

A clean, efficient and mild method is presented for one-pot three-component synthesis of 2-amino-7,7-dimethyl-4-(4-(methylthio)phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile using nickel ferrite magnetic nanoparticles as a recyclable catalyst in green solvent at 40 °C. The structure of the target product was confirmed by FT-IR, 1HNMR, 13CNMR and single crystal X-ray structure analysis. In the present work, the quantum theoretical calculations of the molecular structure of this new compound have been predicted using Density Functional Theory in the solvent DMSO. The geometries of the title compound were optimized by B3LYP/6-31+G* and B3LYP/6-311++G** levels of theory. The electronic spectrum of the title compound in the solvent DMSO was carried out by TDB3LYP/6-311++G** method. Frontier molecular orbitals, molecular electrostatic potential, electronic properties, natural charges and natural bond orbital analysis of the mentioned compound were investigated and discussed by theoretical calculations.

Graphical Abstract

In the present work, the frontier molecular orbitals, molecular electrostatic potential, electronic properties, natural charges and Natural Bond Orbital (NBO) analysis of the mentioned compound were investigated and discussed by theoretical calculations.

Keywords

4H-chromene X-ray single crystal Nickel ferrite Magnetic nanoparticles Green solvent 

Notes

Acknowledgements

The Iranian authors are thankful to the “Iran National science Foundation: INSF” (Grant No. 95841255) for support of this work.

Supplementary material

10870_2019_778_MOESM1_ESM.docx (1.5 mb)
Supplementary material 1 (DOCX 1492 KB)
10870_2019_778_MOESM2_ESM.pdf (107 kb)
Supplementary material 2 (PDF 106 KB)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of ZanjanZanjanIran
  2. 2.Research Institute of Modern Biological TechniquesUniversity of ZanjanZanjanIran
  3. 3.Department of Chemistry, Abhar BranchIslamic Azad UniversityAbharIran
  4. 4.Faculty of ChemistryUniversity of WrocławWrocławPoland
  5. 5.Young Researchers and Elite Club, Gorgan BranchIslamic Azad UniversityGorganIran
  6. 6.Department of Bioscience and BiotechnologyMalek Ashtar University of TechnologyTehranIran
  7. 7.Department of Chemistry, Zanjan BranchIslamic Azad UniversityZanjanIran

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