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

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. © 2020 by the authors. Licensee MDPI, Basel, Switzerland.

Авторы
Kletskov A.V. 1 , Gil D.M.2 , Frontera A.3 , Zaytsev V.P. 1 , Merkulova N.L. 1 , Beltsova K.R. 1 , Sinelshchikova A.A.4 , Grigoriev M.S.4 , Grudova M.V. 1 , Zubkov F.I. 1
Редакторы
-
Журнал
Издательство
MDPI AG
Номер выпуска
5
Язык
Английский
Страницы
-
Статус
Опубликовано
Подразделение
-
Номер
369
Том
10
Год
2020
Организации
  • 1 Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia, RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation
  • 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, Palma de Mallorca, Baleares 07122, Spain
  • 4 Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, bld. 4, Moscow, 119071, Russian Federation
Ключевые слова
1,3,5-Triazacyclohexane; C,H,π interaction; DFT study; H-bonding; Hirshfeld surface analysis; Hybridization of a nitrogen atom in sulfonamides; Triazinane
Дата создания
02.11.2020
Дата изменения
02.11.2020
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/64810/