Molecular structure study of 1,2,3-trimethyldiaziridine by means of gas electron diffraction method

Abstract

The molecular structure of 1,2,3-trimethyldiaziridine has been determined from the gas-phase electron diffraction data supplemented spectral and quantum chemical calculations. The configuration of studied compound incorporates trans-position of methyl groups attached to nitrogen atoms of diaziridine cycle. The following principal structural parameters were determined (r h1 bond lengths in Å, bond angles in degrees with 3σ in parentheses): r(N-C), 1.489(9); r(N-N), 1.480(15); r(C-C), 1.503(15); ∠NCN, 61.5( 9); ∠(H 3 C)CN, 124.0(15). The obtained structural parameters of 1,2,3-trimethyldiaziridine were compared with those for structural analogues. The gaseous standard enthalpy of formation of 1,2,3-trimethyldiaziridine was estimated to be 176.2 ± 5.0 kJ/mol.

Enthalpy of formation of 6-phenyl-1,5-diazabicyclo[3.1.0]hexane by combustion calorimetry and theoretical approach for efficient prediction of thermochemistry of diaziridines

“…Note that it is not always possible to choose a homodesmotic reaction and therefore, it is recommended not to use the G4 method when calculating the enthalpies of formation of polycyclic compounds. The G4 enthalpies of formation of four diaziridines calculated earlier 26–29 are expected to be underestimated up to 10 kJ mol −1 .…”

“…22 The enthalpy of formation values of four diaziridines including 6-cyclopropyl-1,5-diazabicyclo[3.1.0]hexane which is structurally similar to the studied molecule were calculated using the G4 method applied to the atomization reactions. [26][27][28][29] The most accurate method, W1-F12, was used for 1,2-diazaspiro-[2.5]octane (3,3-pentamethylenediaziridine). 30 The well-established Gaussian-4 (G4) composite method 31 is still often used to calculate the enthalpies of formation of organic compounds.…”

New Trends in Diaziridine Formation and Transformation (a Review)

“…Experimental data regarding the structures of diaziridines are important for achieving deeper insight into the previously elucidated features of the diaziridine ring structure, in particular, for the comparison of its corresponding N-N or C-N bond length [21]. Recently, experimental data were obtained for the structural determination of N,N-disubstituted diaziridine [22] and its trisubstituted form, which possesses an additional alkyl group at position 3 [23,24], bis-diaziridine [25], and bicyclic diaziridine [26] derivatives by the method of gas electron diffraction. Most diaziridine derivatives are liquids; thus, the recent experimental determination of its structures on the basis of X-ray diffraction studies [21,27] has only been performed in a few cases.…”

6,6′-Dimethyl-1,1′,5,5′-tetraaza-6,6′-bi(bicyclo[3.1.0]hexane): synthesis and investigation of molecular structure by quantum-chemical calculations, NMR spectroscopy and X-ray diffraction analysis

“…The study of conformational properties and molecular structure of diaziridines (1,2-diazacyclopropanes) comes in a eld of our scienti c interests for many years [1][2][3][4][5][6][7][8][9][10][11][12][13]. The attention to diaziridines is provided by a high theoretical and practical signi cance of this class of compounds.…”