Tutorial 3 - Methoxy Substitution in Perfluoroanthracene

In this example we look at nucleophilic substitution in aromatic perfluorocarbons; specifically methoxy (-OCH3) substitution in perfluoroanthracene.

Perfluoroanthracene is shown schematically in Figure [*] and its structure in Figure [*]. The ring carbon substitution sites are labeled in red and there are effectively three different single-substitution sites: 1, 2 and 9. (Other sites are equivalent by symmetry.)

Image perfluoroanthracene-pure
Perfluoroanthracene showing substitution sites
Image perfluoroanthracene-pure-image

Figures {19}F NMR, and we are going to calculate and compare the {19}F NMR spectra for methoxy substitution at all three sites. Such a study has already been published (M. Muir and J. Baker, J. Fluorine Chem. 126 (2005) 727) and this example duplicates part of this work, showing how PQS and PQSMOL can be used in a real research topic.

Image perfluoroanthracene
1-methoxy-perfluoroanthracene (substitution at site 1)
Image perfluoroanthracene-image

Note: During this tutorial perfluoroanthracene and various methoxy-substituted derivatives will be constructed, and input files will be prepared ready for job submission. However, all the output files have been included on the PQSMOL CD, so there is no need to actually run the jobs. Before starting the tutorial, you should create a test directory and copy all the files in the directory TUTORIALS/EXAMPLE3 on the CD into this directory. Change directory into this test directory before starting the tutorial.