Hückel and Möbius Aromaticity in Charged Sigma Complexes

Mauksch M, Tsogoeva S (2019)

Publication Type: Journal article

Publication year: 2019

Journal

Chemistry - A European Journal Wiley

DOI: 10.1002/chem.201900849

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.

Authors with CRIS profile

Michael Mauksch Lehrstuhl für Anorganische und Metallorganische Chemie Svetlana Tsogoeva 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://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).

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