NMR Crystallography Comparative Studies of Chiral (1R,2S,3R,5R)‑3-Amino-6,6-dimethylbicyclo[3.1.1]heptan-2-ol and Its p‑Toluenesulfonamide Derivative
datasetposted on 05.12.2012, 00:00 by Magdalena Jaworska, Tomasz Pawlak, Rafał Kruszyński, Marta Ćwiklińska, Marek Krzemiński
The crystal structure of (1R,2S,3R,5R)-3-amino-6,6-dimethyl-2-hydroxybicyclo[3.1.1]heptane 1 was determined and it is presented in reference to the structure of (1R,2S,3R,5R)-3-(p-tosylamino)-6,6-dimethyl-2-hydroxybicyclo[3.1.1]heptane 2. 1H and 13C chemical shifts parameters for both structures and for whole unit cells were calculated by using the GIPAW (gauge including projector augmented waves) method. Theoretically calculated chemical shift tensor parameters were verified by 13C CP MAS, 2D PASS, and 13C–1H FSLG HETCOR results to obtain a full structural assignment for 13C and 1H resonances in the solid-state. PISEMA MAS experiment was performed to determine the molecular dynamics of aminoalcohol 1. The comparison of two structures, obtained after all-atom positions optimization after the GIPAW calculations, revealed small conformational differences consistent with the single-crystal X-ray diffaction results.