A. Komasa, E. Bartoszak-Adamska, Z. Dega‐Szafran
Jan 28, 2021
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Journal
Journal of Molecular Structure
Abstract
Abstract N-(2-Hydroxyethyl)morpholine and chloroacetone form a new spirane compound, (R/S)-di-(N-morpholinyl-spiro-β-hydroxy-β-methylmorpholinyl chloride) hydrate (1). The molecular structure and spectroscopic properties of this salt were characterized by the single-crystal X-ray diffraction, DFT calculations, FTIR and NMR spectroscopies. The crystals of compound 1 are monoclinic, P21/c space group. Compound 1 consists of two non-equivalent spiro units (R and S). Each unit is built of two morpholine rings joined at the N(1) spiro center. The spiro units are linked by a water molecule through the O(W)−H(WA)∙∙∙Cl(1) hydrogen bond of 3.141(7) A with R-isomer and by an unusual interaction of water with the electron pair of morpholine oxygen atom of the other S-isomer. The total energy, geometry and natural atomic charges, calculated at the B3LYP/6-311++G(d,p) level of theory, for studied compound and for R and S isomers were analyzed. The C−H••Cl contacts were confirmed by calculations based on the quantum theory of atoms in molecule (QTAIM). The 1H and 13C chemical shifts were assigned by two-dimensional techniques, COSY, HSQC and HMBC. The experimental and computed infrared spectra were compared. The potential energy distribution (PED) was used to assign the vibrational spectra. Diagrams of HOMO and LUMO are presented and discussed.