Crystallographic evidence for global aromaticity in the di-anion and tetra-anion of a cyclophane hydrocarbon

Author:

Stawski Wojciech12ORCID,Zhu Yikun1ORCID,Wei Zheng1ORCID,Petrukhina Marina A.1ORCID,Anderson Harry L.2ORCID

Affiliation:

1. Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222, USA

2. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford OX1 3TA, UK

Abstract

Anionic forms of a macrocyclic cyclophane were crystallized by treating the neutral hydrocarbon with alkali metals (Li, Na and K). The di-anions show decreased bond-length alternation, consistent with global aromaticity, whereas the anti-aromatic tetra-anion has a low-symmetry geometry.

Funder

H2020 European Research Council

National Science Foundation

U.S. Department of Energy

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

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