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Benzyne - an acetylene- or cumulene-like electronic structure?

  • The spatial magnetic properties, through-space NMR shieldings (TSNMRS), of benzyne 1 and analogues (benzene 2, 1,2,3-cyclohexatriene 3, cyclohexen-3-yne 4, cyclohexen-4-yne 5, cyclohexyne 6) have been calculated using the GIAO perturbation method employing the nucleus independent chemical shift (NICS) concept and visualized as iso-chemical-shielding surfaces (ICSS) of various size and direction. The TSNMRS values could be employed to compare the diatropic ring current effects of benzene and benzyne, and, when compared with the spatial magnetic properties of the analogues, to answer the question whether the benzyne electronic structure is more acetylene- or cumulene-like, supported by structural data and delta(C-13)/ppm values. (C) 2019 Published by Elsevier Ltd.

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Metadaten
Author details:Erich KleinpeterORCiDGND, Andreas KochORCiDGND
DOI:https://doi.org/10.1016/j.tet.2019.07.011
ISSN:0040-4020
Title of parent work (English):Tetrahedron
Publisher:Elsevier
Place of publishing:Oxford
Publication type:Article
Language:English
Year of first publication:2019
Publication year:2019
Release date:2020/11/30
Tag:Benzyne-allene or cumulene-like structure; Iso-chemical shielding surfaces (ICSS); NICS; Ring current effect; Trough-space NMR shieldings (TSNMRS)
Volume:75
Issue:33
Number of pages:6
First page:4663
Last Page:4668
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
DDC classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer review:Referiert
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