The equilibrium molecular structure of 3-methyl-4-nitro- and 4-methyl-3-nitrofuroxans by gas-phase electron diffraction and coupled cluster calculations

Belyakov A.V., Oskorbin A.A., Losev V.A., Rykov A.N., Shishkov I.F., Fershtat L.L., Larin A.A., Kuznetsov V.V., Makhova N.N.
Тип документаJournal Article
Дата публикации2020-12-15
Название журналаJournal of Molecular Structure
ИздательElsevier
КвартильQ2
ISSN00222860
  • Organic Chemistry
  • Inorganic Chemistry
  • Spectroscopy
  • Analytical Chemistry
Краткое описание
Abstract The equilibrium molecular structures of the isomeric 3-methyl-4-nitro- and 4-methyl-3-nitrofuroxans have been determined for the first time by gas-phase electron diffraction (GED) supported by coupled cluster calculations up to CCSD(T)/cc-pVTZ level of theory, in frame of dynamic model with relaxation of all structural parameters. The best fit of the experimental scattering intensities was obtained for a model of Cs symmetry. The small differences between similar geometric parameters were constrained at the theoretical values. To compare structural parameters of the titled compounds, the geometries of parent furazan and furoxan molecules were calculated at the CCSD(T)-AE/aug-cc-pVQZ and CCSD(T)-AE/cc-pVQZ levels of theory, respectively. Mean amplitudes and vibrational corrections necessary for GED analysis were computed at the B3LYP/SNDS levels of theory using quadratic and cubic force fields. Peculiar features of electronic and geometric structures of the studied isomeric nitrofuroxans were analyzed with the use of different topological, magnetic and orbital descriptors and the reasons of the significant distinctions between 4- and 3-nitroisomers structures were revealed. Due to hyperconjugation a lone electron pair of exocyclic oxygen atom in both isomers was found to delocalize into antibonding orbital of adjacent O N endocyclic bond, nπ(O)→σ∗(O N). The peculiarity of the 3-nitroisomer structure was provided with the additional interaction of exocyclic and nitro group oxygen atoms.
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1. Belyakov A.V. и др. The equilibrium molecular structure of 3-methyl-4-nitro- and 4-methyl-3-nitrofuroxans by gas-phase electron diffraction and coupled cluster calculations // Journal of Molecular Structure. 2020. Т. 1222. С. 128856.
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TY - JOUR

DO - 10.1016/j.molstruc.2020.128856

UR - http://dx.doi.org/10.1016/j.molstruc.2020.128856

TI - The equilibrium molecular structure of 3-methyl-4-nitro- and 4-methyl-3-nitrofuroxans by gas-phase electron diffraction and coupled cluster calculations

T2 - Journal of Molecular Structure

AU - Belyakov, A.V.

AU - Oskorbin, A.A.

AU - Losev, V.A.

AU - Rykov, A.N.

AU - Shishkov, I.F.

AU - Fershtat, L.L.

AU - Larin, A.A.

AU - Kuznetsov, V.V.

AU - Makhova, N.N.

PY - 2020

DA - 2020/12

PB - Elsevier BV

SP - 128856

VL - 1222

SN - 0022-2860

ER -

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@article{2020,

doi = {10.1016/j.molstruc.2020.128856},

url = {https://doi.org/10.1016%2Fj.molstruc.2020.128856},

year = 2020,

month = {dec},

publisher = {Elsevier {BV}},

volume = {1222},

pages = {128856},

author = {A.V. Belyakov and A.A. Oskorbin and V.A. Losev and A.N. Rykov and I.F. Shishkov and L.L. Fershtat and A.A. Larin and V.V. Kuznetsov and N.N. Makhova},

title = {The equilibrium molecular structure of 3-methyl-4-nitro- and 4-methyl-3-nitrofuroxans by gas-phase electron diffraction and coupled cluster calculations}

}

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Belyakov, A.V. et al. “The Equilibrium Molecular Structure of 3-Methyl-4-Nitro- and 4-Methyl-3-Nitrofuroxans by Gas-Phase Electron Diffraction and Coupled Cluster Calculations.” Journal of Molecular Structure 1222 (2020): 128856. Crossref. Web.