Hückel and Möbius Aromaticity in Charged Sigma Complexes

Journal article


Publication Details

Author(s): Mauksch M, Tsogoeva S
Journal: Chemistry - A European Journal
Publication year: 2019
ISSN: 0947-6539
eISSN: 1521-3765


Abstract


In sigma complexes, intermediates in nucleophilic and electrophilic aromatic substitution and other reactions, delocalization in the aromatic ring is formally disrupted. Unexpectedly, computational evidence is presented that favorable processes contain aromatic sigma complexes. Tetracoordinated carbon therein surprisingly employs orbitals that are more similar to sp
2
than to sp
3
hybrids in sigma bonds with adjacent ring atoms. Both leaving groups and nucleo- or electrophiles may donate electrons to the π-system depending on the availability of p-type orbitals to fulfill Hückel (4N+2) or Möbius (4N) rules of aromaticity in analogy to conjugated transition-metal metallacycles.


FAU Authors / FAU Editors

Mauksch, Michael Dr.
Lehrstuhl für Anorganische und Metallorganische Chemie
Tsogoeva, Svetlana Prof. Dr.
Professur für Organische Chemie


How to cite

APA:
Mauksch, M., & Tsogoeva, S. (2019). Hückel and Möbius Aromaticity in Charged Sigma Complexes. Chemistry - A European Journal. https://dx.doi.org/10.1002/chem.201900849

MLA:
Mauksch, Michael, and Svetlana Tsogoeva. "Hückel and Möbius Aromaticity in Charged Sigma Complexes." Chemistry - A European Journal (2019).

BibTeX: 

Last updated on 2019-27-05 at 11:08