3-Cyclopropyl-1,2-dimethyldiaziridine: synthesis and study of molecular structure by gas electron diffraction method |
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Authors: | Ekaterina P. Altova Vladimir V. Kuznetsov Ilya I. Marochkin Anatolii N. Rykov Nina N. Makhova Igor F. Shishkov |
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Affiliation: | 1.Chemistry Department,Lomonosov Moscow State University,Moscow,Russian Federation;2.N. D. Zelinsky Institute of Organic Chemistry,Russian Academy of Sciences,Moscow,Russian Federation |
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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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