Abstract
1,4,5,8-tetrakis(perfluoropyridin-4-yloxy)naphthalene (tetra-PPN) was synthesized via a one-pot pseudo-five-component reaction of pentafluoropyridine and 5,8-dihydroxy-1,4-tetralindione under basic conditions in DMF. The asymmetric unit contains one half-mol ecule of tetra-PPN and data reveals that half of the molecule being related to the other via inversion symmetry. A detailed analysis of the intermolecular interactions of the compound has been performed using Hirshfeld surfaces. The optimized geometrical parameters and calculated spectroscopic features obtained by quantum chemical calculations using density functional (DFT) methods. In addition, to support the experimental results, the 19F NMR values are obtained using B3LYP method. The obtained results are compared with experimental values show a very good agreement with the experimental data.
Highlights
Organofluorine compounds find many different applications, ranging from pharmaceuticals and agrochemicals to advanced materials and polymers [1]
We have described the synthesis of some 4-substituted tetrafluoropyridine systems from reaction of pentafluoropyridine with tetrazole-5-thiol, piperazine, hydroxylated naphtoquinones and antraquinones [10,11,12]
We describe the reaction of pentafluoropyridine with 5,8-dihydroxy-1,4-tetralindione, resulting in 1,4,5,8-tetrakis(perfluoropyridin-4-yloxy)naphthalene (Figure 1)
Summary
Organofluorine compounds find many different applications, ranging from pharmaceuticals and agrochemicals to advanced materials and polymers [1]. Circa 30−40% of agrochemicals and 20% of pharmaceuticals contain at least one fluorine atom [2,3]. Many perfluoroheteroaromatic compounds such as perfluoroquinoline [4] and pentafluoropyridine, in which all the hydrogen atoms of the heterocyclic rings have been replaced by fluorine atoms, have been investigated since the early 1960s [2,5,6]. The most important reaction of pentafluoropyridines involves the replacement of the para-fluorine atom by nucleophilic reagents allowing the synthesis of new organofluorine compounds such as heterocyclic and macrocyclic perfluoro systems [7,8,9]. The geometric structural parameters and 19F NMR results were calculated and compared with the experimental results
Sign-in/Register to view highlights & summary 
Published Version (
Free)
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Structural Chemistry & Crystallography Communication
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
