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

  • 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.

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Metadaten
Author:Erich Kleinpeter, Stefanie Kriiger, Andreas Koch
DOI:https://doi.org/10.1021/acs.jpca.5b03078
ISSN:1089-5639 (print)
Pubmed Id:http://www.ncbi.nlm.nih.gov/pubmed?term=25860405
Parent Title (English):The journal of physical chemistry : A, Molecules, spectroscopy, kinetics, environment & general theory
Publisher:American Chemical Society
Place of publication:Washington
Document Type:Article
Language:English
Year of first Publication:2015
Year of Completion:2015
Release Date:2017/03/27
Volume:119
Issue:18
Pagenumber:9
First Page:4268
Last Page:4276
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert