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Research on Chemical Intermediates

, Volume 42, Issue 3, pp 1593–1610 | Cite as

Regio-selective synthesis of 5-substituted 1H-tetrazoles using ionic liquid [BMIM]N3 in solvent-free conditions: a click reaction

  • Soheila Khaghaninejad
  • Majid M. Heravi
  • Tayebeh Hosseinnejad
  • Hossein A. Oskooie
  • Mehdi Bakavoli
Article

Abstract

A multi-component, one pot and regio-selective synthesis of different 5-substituted 1H-tetrazoles was successfully accomplished via a click reaction. In this respect, we have performed the reaction of either isatins or various aromatic aldehydes with malononitrile and ionic liquid, 1-butyl-3-methylimidazolium azide ([BMIM]N3), as a relatively green source of azide mediated by o-phthalimide-N-sulfonic acid (OPNSA). The calculated thermodynamic results demonstrate a reliable agreement with our experimentally observed regio-selectivity. From the electronic viewpoint, we have also assessed the nature of regio-selectivity via quantum theory of atoms in molecule analysis.

Graphical Abstract

Keywords

Click reaction Ionic liquid: 1-butyl-3-methylimidazolium azide 5-Substituted 1H-tetrazoles Density functional theory Quantum theory of atoms in molecule Regio-selectivity 

List of symbols

T

Temperature (°C)

t

Time (t)

ρb

Values of electron density

2ρb

Laplacian of ρ b

Gb

Electronic kinetic energy density

Vb

Electronic potential energy density

Hb

Total electronic energy density

ΔEe,r

The reaction energy from the total electronic energies

ΔE0,r

The reaction energy with zero-point energies

ΔHr

Reaction enthalpy

ΔGr

Free energy

ΔSr

Entropy change

Notes

Acknowledgments

M. M. Heravi is thankful to the Reaearch Council of Alzahra University for partial financial assistance.

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Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Soheila Khaghaninejad
    • 1
  • Majid M. Heravi
    • 1
  • Tayebeh Hosseinnejad
    • 1
  • Hossein A. Oskooie
    • 1
  • Mehdi Bakavoli
    • 2
  1. 1.Department of Chemistry, School of ScienceAlzahra UniversityVanak, TehranIran
  2. 2.Department of Chemistry, School of ScienceFerdowsi University of MashhadMashhadIran

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