Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group

N-t-Bu-N’,N’’-disulfonamide-1,3,5-triazinanes were synthesized and characterized by X-ray single crystal structure analysis. In the course of the X-ray structure elucidation, the first solid experimental evidence of the axial position of the tert-butyl group in unconstrained hexahydro-1,3,5-triazacyclohexanes was obtained. Dynamic low-temperature NMR analysis allowed to fully investigate a rare case of crystallization-driven unanchoring of the tert-butyl group in the chair conformation of saturated sixmembered cycles. DFT calculations show that the use of explicit solvent molecules is necessary to explain the equatorial position of the t-Bu group in solution. Otherwise, the axial conformer is the thermodynamically stable isomer.Fil: Kletskov, Alexey V.. University of Russia; RusiaFil: Zatykina, Anastasya D.. University of Russia; RusiaFil: Grudova, Mariya V.. University of Russia; RusiaFil: Sinelshchikova, Anna A.. Academy of Sciences; RusiaFil: Grigoriev, Mikhail. Academy of Sciences; RusiaFil: Zaytsev, Vladimir P.. University of Russia; RusiaFil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Novikov, Roman A.. Academy of Sciences; RusiaFil: Zubkov, Fedor Ivanovich. University of Russia; RusiaFil: Frontera, Antonio. Universidad de las Islas Baleares; Españ