Journal of Physical Chemistry A, volume 112, issue 23, pages 5243-5250
Molecular structure of 1,5-diazabicyclo[3.1.0]hexane as determined by gas electron diffraction and quantum-chemical calculations
Vishnevskiy Yuri V
1
,
Vogt Natalja
1
,
VOGT JÜRGEN
1
,
RYKOV A. N.
1
,
Kuznetsov V. V.
1
,
Makhova Nina N.
1
,
Vilkov Lev V.
1
Publication type: Journal Article
Publication date: 2008-05-20
Journal:
Journal of Physical Chemistry A
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.9
ISSN: 10895639, 15205215
Physical and Theoretical Chemistry
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 degrees 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 C s 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 (r(e), A and angle)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) --> sigma*(C-C) anomeric effect. The geometry calculations and NBO analysis have been performed also for the bicyclohexane molecule.
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Vishnevskiy Y. V. et al. Molecular structure of 1,5-diazabicyclo[3.1.0]hexane as determined by gas electron diffraction and quantum-chemical calculations // Journal of Physical Chemistry A. 2008. Vol. 112. No. 23. pp. 5243-5250.
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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 // Journal of Physical Chemistry A. 2008. Vol. 112. No. 23. pp. 5243-5250.
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TY - JOUR
DO - 10.1021/jp801346v
UR - https://doi.org/10.1021%2Fjp801346v
TI - Molecular structure of 1,5-diazabicyclo[3.1.0]hexane as determined by gas electron diffraction and quantum-chemical calculations
T2 - Journal of Physical Chemistry A
AU - Vishnevskiy, Yuri V
AU - VOGT, JÜRGEN
AU - Vilkov, Lev V.
AU - Vogt, Natalja
AU - RYKOV, A. N.
AU - Kuznetsov, V. V.
AU - Makhova, Nina N.
PY - 2008
DA - 2008/05/20 00:00:00
PB - American Chemical Society (ACS)
SP - 5243-5250
IS - 23
VL - 112
SN - 1089-5639
SN - 1520-5215
ER -
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@article{2008_Vishnevskiy,
author = {Yuri V Vishnevskiy and JÜRGEN VOGT and Lev V. Vilkov and Natalja Vogt and A. N. RYKOV and V. V. Kuznetsov and Nina N. Makhova},
title = {Molecular structure of 1,5-diazabicyclo[3.1.0]hexane as determined by gas electron diffraction and quantum-chemical calculations},
journal = {Journal of Physical Chemistry A},
year = {2008},
volume = {112},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021%2Fjp801346v},
number = {23},
pages = {5243--5250},
doi = {10.1021/jp801346v}
}
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Vishnevskiy, Yuri V., et al. “Molecular structure of 1,5-diazabicyclo[3.1.0]hexane as determined by gas electron diffraction and quantum-chemical calculations.” Journal of Physical Chemistry A, vol. 112, no. 23, May. 2008, pp. 5243-5250. https://doi.org/10.1021%2Fjp801346v.