Visualisation of chemical shielding tensors (VIST) to elucidate aromaticity and antiaromaticity
File(s)ejoc.202100352.pdf (3.84 MB)
Published version
Author(s)
Plasser, Felix
Glöcklhofer, Florian
Type
Journal Article
Abstract
Aromaticity is a central concept in chemistry, pervading areas from biochemistry to materials science. Recently, chemists also started to exploit intricate phenomena such as the interplay of local and global (anti)aromaticity or aromaticity in non‐planar systems and three dimensions. These phenomena pose new challenges in terms of our fundamental understanding and the practical visualisation of aromaticity. To overcome these challenges, a method for the visualisation of chemical shielding tensors (VIST) is developed here that allows for a 3D visualisation with quantitative information about the local variations and anisotropy of the chemical shielding. After exemplifying the method in different planar hydrocarbons, we study two non‐planar macrocycles to show the unique benefits of the VIST method for molecules with competing π‐conjugated systems and conclude with a norcorrole dimer showing clear evidence of through‐space aromaticity. We believe that the VIST method will be a highly valuable addition to the computational toolbox.
Date Issued
2021-05-07
Date Acceptance
2021-04-01
Citation
European Journal of Organic Chemistry, 2021, 2021 (17), pp.2529-2539
ISSN
1434-193X
Publisher
Wiley
Start Page
2529
End Page
2539
Journal / Book Title
European Journal of Organic Chemistry
Volume
2021
Issue
17
Copyright Statement
© 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
License URL
Sponsor
EPRSC
Engineering & Physical Science Research Council (EPSRC)
FWF Austrian Science Fund (FWF)
Identifier
https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100352
Grant Number
EP/V048686/1
EP/V048686/1
J 4463
Subjects
Organic Chemistry
0304 Medicinal and Biomolecular Chemistry
0305 Organic Chemistry
Publication Status
Published
Date Publish Online
2021-04-07