Rational Computational Design of Systems Exhibiting Strong Halogen Bonding Involving Fluorine in Bicyclic Diamine Derivatives

Perhaps the most controversial and rare aspect of the halogen bonding interaction is the potential of fluorine in compounds to serve as a halogen bond donor. In this note, we provide clear and convincing examples of hypothetical molecules in which fluorine is strongly halogen bonding in a metastable state. Of particular note is a polycyclic system inspired by Selectfluor, which has been controversially proposed to engage in halogen bonding.

Automated summary

The potential of fluorine in compounds to serve as a halogen bond donor is a controversial and rare aspect of halogen bonding interaction. This note presents clear and convincing examples of hypothetical molecules where fluorine forms strong halogen bonding in a metastable state. Of particular interest is a polycyclic system inspired by Selectfluor, which has been controversially proposed as being involved in halogen bonding.