Intramolecular <i>sp</i><sup>2</sup>-<i>sp</i><sup>3</sup> Disequalization of Chemically Identical Sulfonamide Nitrogen Atoms: Single Crystal X-Ray Diffraction Characterization, Hirshfeld Surface Analysis and DFT Calculations of <i>N</i>-Substituted Hexahydro-1,3,5-Triazines
Alexey V. Kletskov,
Diego M. Gil,
Antonio Frontera,
Vladimir P. Zaytsev,
Natalia L. Merkulova,
Ksenia R. Beltsova,
Anna A. Sinelshchikova,
Mikhail S. Grigoriev,
Mariya V. Grudova,
Fedor I. Zubkov
Affiliations
Alexey V. Kletskov
Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russia
Diego M. Gil
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
Antonio Frontera
Department de Química, Universitat de les Illes Balears, Crta de Valldemossa km 7.5, 07122 Palma de Mallorca (Baleares), Spain
Vladimir P. Zaytsev
Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russia
Natalia L. Merkulova
Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russia
Ksenia R. Beltsova
Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russia
Anna A. Sinelshchikova
Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, bld. 4, Moscow 119071, Russia
Mikhail S. Grigoriev
Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, bld. 4, Moscow 119071, Russia
Mariya V. Grudova
Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russia
Fedor I. Zubkov
Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russia
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.
