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Intramolecular sp2-sp3 Disequalization of Chemically Identical Sulfonamide Nitrogen Atoms: Single Crystal X-Ray Diffraction Characterization, Hirshfeld Surface Analysis and DFT Calculations of N-Substituted Hexahydro-1,3,5-Triazines

1
Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russia
2
INBIOFAL (CONICET-UNT), Instituto de Química Orgánica-Cátedra de Química Orgánica I, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, San Miguel de Tucumán, Tucumán T4000INI, Argentina
3
Department de Química, Universitat de les Illes Balears, Crta de Valldemossa km 7.5, 07122 Palma de Mallorca (Baleares), Spain
4
Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, bld. 4, Moscow 119071, Russia
*
Authors to whom correspondence should be addressed.
Crystals 2020, 10(5), 369; https://doi.org/10.3390/cryst10050369
Received: 2 April 2020 / Revised: 20 April 2020 / Accepted: 23 April 2020 / Published: 4 May 2020
(This article belongs to the Special Issue σ- and π-Hole Interactions)
In this manuscript, the synthesis and single crystal X-ray diffraction characterization of four N-substituted 1,3,5-triazinanes are reported along with a detailed analysis of the noncovalent interactions observed in the solid state architecture to these compounds, focusing on C–H···π and C–H···O H-bonding interactions. These noncovalent contacts have been characterized energetically by using DFT calculations and also by Hirshfeld surface analysis. In addition, the supramolecular assemblies have been characterized using the quantum theory of “atoms-in-molecules” (QTAIM) and molecular electrostatic potential (MEP) calculations. The XRD analysis revealed a never before observed feature of the crystalline structure of some molecules: symmetrically substituted 1,3,5-triazacyclohexanes possess two chemically identical sulfonamide nitrogen atoms in different sp2 and sp3-hybridizations. View Full-Text
Keywords: triazinane; 1,3,5-Triazacyclohexane; Hirshfeld surface analysis; DFT study; H-bonding; C–H···π interaction; hybridization of a nitrogen atom in sulfonamides triazinane; 1,3,5-Triazacyclohexane; Hirshfeld surface analysis; DFT study; H-bonding; C–H···π interaction; hybridization of a nitrogen atom in sulfonamides
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Kletskov, A.V.; Gil, D.M.; Frontera, A.; Zaytsev, V.P.; Merkulova, N.L.; Beltsova, K.R.; Sinelshchikova, A.A.; Grigoriev, M.S.; Grudova, M.V.; Zubkov, F.I. Intramolecular sp2-sp3 Disequalization of Chemically Identical Sulfonamide Nitrogen Atoms: Single Crystal X-Ray Diffraction Characterization, Hirshfeld Surface Analysis and DFT Calculations of N-Substituted Hexahydro-1,3,5-Triazines. Crystals 2020, 10, 369.

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