Molecular Structure of 1,5-Diazabicyclo[3.1.0]hexane as Determined by Gas Electron Diffraction and Quantum-Chemical Calculations

Vishnevskiy YV, Vogt N, Vogt J, Rykov AN, Kuznetsov VV, Makhova NN, Vilkov LV (2008)
The Journal of Physical Chemistry A 112(23): 5243-5250.

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Abstract
The equilibrium molecular structure and conformation of 1,5-diazabicyclo[3.1.0]hexane (DABH) has been studied by the gas-phase electron-diffraction method at 20 °C and quantum-chemical calculations. Three possible conformations of DABH were considered: boat, chair, and twist. According to the experimental and theoretical results, DABH exists exclusively as a boat conformation of Cs symmetry at the temperature of the experiment. The MP2 calculations predict the stable chair and twist conformations to be 3.8 and 49.5 kcal mol−1 above the boat form, respectively. The most important semi-experimental geometrical parameters of DABH (re, Å and ∠e, deg) are (N1−N5) = 1.506(13), (N1−C6) = 1.442(2), (N1−C2) = 1.469(4), (C2−C3) = 1.524(7), (C6−N1−C2) = 114.8(8), (N5−N1−C2) = 107.7(4), (N1−C2−C3) = 106.5(9), and (C2−C3−C4) = 104.0(10). The natural bond orbital (NBO) analysis has shown that the most important stabilization factor in the boat conformation is the n(N) → σ*(C−C) anomeric effect. The geometry calculations and NBO analysis have been performed also for the bicyclohexane molecule.
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Vishnevskiy YV, Vogt N, Vogt J, et al. Molecular Structure of 1,5-Diazabicyclo[3.1.0]hexane as Determined by Gas Electron Diffraction and Quantum-Chemical Calculations. The Journal of Physical Chemistry A. 2008;112(23):5243-5250.
Vishnevskiy, Y. V., Vogt, N., Vogt, J., Rykov, A. N., Kuznetsov, V. V., Makhova, N. N., & Vilkov, L. V. (2008). Molecular Structure of 1,5-Diazabicyclo[3.1.0]hexane as Determined by Gas Electron Diffraction and Quantum-Chemical Calculations. The Journal of Physical Chemistry A, 112(23), 5243-5250.
Vishnevskiy, Y. V., Vogt, N., Vogt, J., Rykov, A. N., Kuznetsov, V. V., Makhova, N. N., and Vilkov, L. V. (2008). Molecular Structure of 1,5-Diazabicyclo[3.1.0]hexane as Determined by Gas Electron Diffraction and Quantum-Chemical Calculations. The Journal of Physical Chemistry A 112, 5243-5250.
Vishnevskiy, Y.V., et al., 2008. Molecular Structure of 1,5-Diazabicyclo[3.1.0]hexane as Determined by Gas Electron Diffraction and Quantum-Chemical Calculations. The Journal of Physical Chemistry A, 112(23), p 5243-5250.
Y.V. Vishnevskiy, et al., “Molecular Structure of 1,5-Diazabicyclo[3.1.0]hexane as Determined by Gas Electron Diffraction and Quantum-Chemical Calculations”, The Journal of Physical Chemistry A, vol. 112, 2008, pp. 5243-5250.
Vishnevskiy, Y.V., Vogt, N., Vogt, J., Rykov, A.N., Kuznetsov, V.V., Makhova, N.N., Vilkov, L.V.: Molecular Structure of 1,5-Diazabicyclo[3.1.0]hexane as Determined by Gas Electron Diffraction and Quantum-Chemical Calculations. The Journal of Physical Chemistry A. 112, 5243-5250 (2008).
Vishnevskiy, Yuri V., Vogt, Natalja, Vogt, Jürgen, Rykov, Anatolii N., Kuznetsov, Vladimir V., Makhova, Nina N., and Vilkov, Lev V. “Molecular Structure of 1,5-Diazabicyclo[3.1.0]hexane as Determined by Gas Electron Diffraction and Quantum-Chemical Calculations”. The Journal of Physical Chemistry A 112.23 (2008): 5243-5250.
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Structure and bonding nature of the strained Lewis acid 3-methyl-1-boraadamantane: a case study employing a new data-analysis procedure in gas electron diffraction.
Vishnevskiy YV, Abaev MA, Rykov AN, Gurskii ME, Belyakov PA, Erdyakov SY, Bubnov YN, Mitzel NW., Chemistry 18(34), 2012
PMID: 22791415

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