Study of host–guest interactions in benzodiazacoronands by means of solid state NMRspectroscopy, X-ray diffraction and quantum mechanical computations

Literature Information

Publication Date 2011-03-08
DOI 10.1039/C0CP02401E
Impact Factor 3.676
Authors

Katarzyna Nowicka, Anna Bujacz, Piotr Paluch, Adam Sobczuk, Agata Jeziorna, Włodzimierz Ciesielski, Grzegorz D. Bujacz, Janusz Jurczak, Marek J. Potrzebowski


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Abstract

In this work we present solid state data for five host–guest complexes formed by N-(4,19-dioxo-2,8,15,21-tetraoxa-5,18-diazatricyclohexacosa-1(25),9(14),10,12,22(26),23-hexaen-26-yl)-benzamide (1) belonging to the group of benzodiazacoronands, achiral compounds for which chiral crystals were found (J. Kalisiak and J. Jurczak, Cryst. Growth Des., 2006, 6, 20). The X-ray structure was resolved for four of them. It was found that 1 crystallizes in P21/c, P and P21/n achiral space groups. Differentiation of molecular packing and the presence of guest molecules within the crystal lattice were analyzed with solid state NMR. An attempt was made to correlate changes in 13C δii and 15N δii chemical shift tensor values, obtained from analysis of spinning sidebands of 1D and 2D (2D PASS) NMR spectra, with changes in the strength of hydrogen bonding. Quantum mechanical DFT GIAO calculations of NMR shielding parameters carried out on structures with coordinates taken from XRD were employed for signals assignment and verification of structural constraints.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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