Anisotropy Effect of Three-Membered Rings in H-1 NMR Spectra: Quantification by TSNMRS and Assignment of the Stereochemistry

作者：Kleinpeter Erich^*; Kriiger Stefanie; Koch Andreas

来源：Journal of Physical Chemistry A, 2015, 119(18): 4268-4276.

DOI：10.1021/acs.jpca.5b03078

The spatial magnetic properties (through Space NAIR shieldings, TSNMRSs) of cyclopropane; of the heteroanalogous oxirane, thiirane, and aziridine; and of various substituted dis-, and tris-cyclic analogues have been computed by the GIAO perturbation method employing the nucleus independent chemical shift (NICS) concept and visualized as iso-chemical-shielding surfaces (ICSSs) of various size and direction. The TSNMRS values, thus obtained, can be employed to visualize the anisotropy (ring current) effect of I the cyclopropane ring moiety. This approach has been employed to qualify and quantify substituent influences and contributions of appropriate ring heteroatoms O, NH, and S on the anisotropy (ring current) effect of three-mernbered ring moieties, and to assign the stereochemistry of mono-, bis-, and tris cyclic structures containing cyclopropane as a structural element. Characteristic examples are included.

• 出版日期2015-5-7