4 years ago

Isolation of an Antiaromatic Singlet Cyclopentadienyl Zwitterion

Isolation of an Antiaromatic Singlet Cyclopentadienyl Zwitterion
Iris Trosien, Wolfram Sander, Joel Mieres-Perez, Paolo Costa
The reaction of triplet tetrachlorocyclopentadienylidene with BF3 in rare gas matrices yields a zwitterion consisting of a cyclopentadienyl cation bearing a positive charge and a negatively charged BF3 unit. IR and UV–vis spectra as well as the absence of EPR signals demonstrate a singlet ground state of the zwitterion, and its calculated geometry and magnetic properties clearly reveal a strong antiaromatic character. The zwitterion is highly labile and by visible or IR irradiation rearranges via a 1,2-fluorine migration from boron to carbon. Interaction with a second molecule of BF3 stabilizes the zwitterion and suppresses the fluorine migration, thus providing a convenient and efficient synthesis of an antiaromatic molecule under very mild conditions.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05807

DOI: 10.1021/jacs.7b05807

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.