Comparing the properties of naphthalene and azulene via theory and experiment: Past, present, and future

CHED 482

Carl Salter, csalter@chem.moravian.edu, Department of Chemistry, Moravian College, 1200 Main Street, Bethlehem, PA 18018 and James B. Foresman, JForesma@YCP.EDU, Department of Physical Science, York College of PA, Country Club Road, York, PA 17405.
We believe that a junior-year laboratory experience such as physical chemistry should give students the opportunity to build and test rigorous chemical models. To that end we are constructing experiments around naphthalene and its geometric isomer azulene in which students predict the differences in their properties through high-level computational chemistry, and then test those predictions in the laboratory. One such experiment involving bomb calorimetry has already been published (JCE 1998, v 75, p 1341). We will review that experiment which compares their heats of formation and discuss the development of experiments comparing their UV, IR, and NMR spectral properties and their reactivity to electrophilic aromatic substitution.