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Structural Chemistry

, Volume 29, Issue 3, pp 815–822 | Cite as

3-Cyclopropyl-1,2-dimethyldiaziridine: synthesis and study of molecular structure by gas electron diffraction method

  • Ekaterina P. AltovaEmail author
  • Vladimir V. Kuznetsov
  • Ilya I. Marochkin
  • Anatolii N. Rykov
  • Nina N. Makhova
  • Igor F. Shishkov
Original Research

Abstract

The molecular structure and conformational behavior of 3-cyclopropyl-1,2-dimethyldiaziridine have been for the first time experimentally studied by gas-phase electron diffraction and quantum chemical calculations. The two most stable conformers at 298 K possess anti and gauche mutual ring orientation (with prevalence of the anti conformer) whereas only one anti conformer is observed in solution. The determined structural parameters of gaseous 3-cyclopropyl-1,2-dimethyldiaziridine have been compared with those for 3,3-bidiaziridine structural analogues in the crystal phase. The simple and convenient procedure for the synthesis of 3-cyclopropyl-1,2-dimethyldiaziridine comprising cyclopropane and diaziridine rings in one molecule was developed. The standard enthalpy of formation of 3-cyclopropyl-1,2-dimethyldiaziridine in the gas phase was calculated using Gaussian-4 theory, yielding value of 281.9 ± 5.0 kJ/mol.

Keywords

Gas-phase electron diffraction Cyclopropyldiaziridine Synthesis NMR Enthalpy of formation 

Notes

Acknowledgments

Authors thank Dr. V.V. Kachala for the NMR-spectra investigation.

Funding information

This study has been supported by Russian Foundation for Basic Research (Project 16-33-00130 mol_a).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflicts of interest.

Supplementary material

11224_2018_1104_MOESM1_ESM.doc (302 kb)
ESM 1 (DOC 302 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Ekaterina P. Altova
    • 1
    Email author
  • Vladimir V. Kuznetsov
    • 2
  • Ilya I. Marochkin
    • 1
  • Anatolii N. Rykov
    • 1
  • Nina N. Makhova
    • 2
  • Igor F. Shishkov
    • 1
  1. 1.Chemistry DepartmentLomonosov Moscow State UniversityMoscowRussian Federation
  2. 2.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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