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

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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.

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Acknowledgments

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

Funding

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

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Authors and Affiliations

  1. Chemistry Department, Lomonosov Moscow State University, Leninsky Gory 1, Moscow, Russian Federation, 119991

    Ekaterina P. Altova, Ilya I. Marochkin, Anatolii N. Rykov & Igor F. Shishkov

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp, Moscow, Russian Federation, 119991

    Vladimir V. Kuznetsov & Nina N. Makhova

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  1. Ekaterina P. Altova
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  2. Vladimir V. Kuznetsov
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  3. Ilya I. Marochkin
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  4. Anatolii N. Rykov
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  5. Nina N. Makhova
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  6. Igor F. Shishkov
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Correspondence to Ekaterina P. Altova.

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Altova, E.P., Kuznetsov, V.V., Marochkin, I.I. et al. 3-Cyclopropyl-1,2-dimethyldiaziridine: synthesis and study of molecular structure by gas electron diffraction method. Struct Chem 29, 815–822 (2018). https://doi.org/10.1007/s11224-018-1104-6

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  • DOI: https://doi.org/10.1007/s11224-018-1104-6

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