Journal of Molecular Structure, volume 1222, pages 128856

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

Belyakov Alexander V ¹

Oskorbin A A ¹

Losev V A ¹

RYKOV A. N. ²

Shishkov Igor F. ²

Fershtat Leonid L. ³

Larin Alexander A ³

Kuznetsov V. V. ³

Makhova Nina N. ³

Hide authors affiliations Show authors affiliations: 3 affiliations

Saint-Petersburg State Technological Institute, 190013, Saint Petersburg, Russia |

Department of Chemistry, Moscow State University, 119992 Moscow - Russia |

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia. |

Publication type: Journal Article

Publication date: 2020-12-01

Elsevier

Journal: Journal of Molecular Structure

Quartile SCImago

Quartile WOS

Impact factor: 3.8

ISSN: 00222860

DOI: 10.1016/j.molstruc.2020.128856

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Organic Chemistry

Inorganic Chemistry

Spectroscopy

Analytical Chemistry

Abstract

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
Molecules	Molecules, 1, 14.29% Molecules 1 publication, 14.29%
Journal of Molecular Liquids	Journal of Molecular Liquids, 1, 14.29% Journal of Molecular Liquids 1 publication, 14.29%
Journal of Molecular Structure	Journal of Molecular Structure, 1, 14.29% Journal of Molecular Structure 1 publication, 14.29%
Fine Chemical Technologies	Fine Chemical Technologies, 1, 14.29% Fine Chemical Technologies 1 publication, 14.29%
Chemical Physics Letters	Chemical Physics Letters, 1, 14.29% Chemical Physics Letters 1 publication, 14.29%
Mendeleev Communications	Mendeleev Communications, 1, 14.29% Mendeleev Communications 1 publication, 14.29%
Overlap Determinant Method in the Theory of Pericyclic Reactions	Overlap Determinant Method in the Theory of Pericyclic Reactions, 1, 14.29% Overlap Determinant Method in the Theory of Pericyclic Reactions 1 publication, 14.29%
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Elsevier	Elsevier, 4, 57.14% Elsevier 4 publications, 57.14%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 14.29% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 14.29%
RTU MIREA	RTU MIREA, 1, 14.29% RTU MIREA 1 publication, 14.29%
Springer Nature	Springer Nature, 1, 14.29% Springer Nature 1 publication, 14.29%
	1 2 3 4

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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. 2020. Vol. 1222. p. 128856.

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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. 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. Vol. 1222. p. 128856.

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RIS Copy

TY - JOUR

DO - 10.1016/j.molstruc.2020.128856

UR - https://doi.org/10.1016%2Fj.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, Alexander V

AU - Oskorbin, A A

AU - Losev, V A

AU - RYKOV, A. N.

AU - Shishkov, Igor F.

AU - Fershtat, Leonid L.

AU - Larin, Alexander A

AU - Kuznetsov, V. V.

AU - Makhova, Nina N.

PY - 2020

DA - 2020/12/01 00:00:00

PB - Elsevier

SP - 128856

VL - 1222

SN - 0022-2860

ER -

BibTex

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BibTex Copy

@article{2020_Belyakov,

author = {Alexander V Belyakov and A A Oskorbin and V A Losev and A. N. RYKOV and Igor F. Shishkov and Leonid L. Fershtat and Alexander A Larin and V. V. Kuznetsov and Nina 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},

journal = {Journal of Molecular Structure},

year = {2020},

volume = {1222},

publisher = {Elsevier},

month = {dec},

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

pages = {128856},

doi = {10.1016/j.molstruc.2020.128856}

}

Found error?

Publisher

Elsevier

Journal

Journal of Molecular Structure

Quartile SCImago

Quartile WOS

Impact factor

3.8

ISSN

00222860 (Print)

Labs

Laboratory of Nitrogen-Containing Compounds

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