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

• Published in: Structural chemistry Vol. 29; no. 3; pp. 815 - 822
• Main Authors: Altova, Ekaterina P., Kuznetsov, Vladimir V., Marochkin, Ilya I., Rykov, Anatolii N., Makhova, Nina N., Shishkov, Igor F.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-06-2018; Springer Nature B.V
• Subjects: Chemical synthesis; Chemistry; Chemistry and Materials Science; Computer Applications in Chemistry; Crystal structure; Cyclopropane; Electron diffraction; Enthalpy; Mathematical analysis; Molecular chains; Molecular structure; Organic compounds; Original Research; Physical Chemistry; Quantum chemistry; Theoretical and Computational Chemistry; Gas-phase electron diffraction; NMR; Enthalpy of formation; Synthesis; Cyclopropyldiaziridine
• ISSN: 1040-0400; 1572-9001
• DOI: 10.1007/s11224-018-1104-6

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.