Abstract
Abstract A 1:1 mole-ratio mixture of anthracene and naphthalene was pyrolyzed in a drop-tube furnace. the product mixture was analyzed by high performance liquid chromatography with diode-array, UV-absorption spectrometric detection (HPLC/DAD) and by gas chromatography/mass spectrometry (GCMS). In addition to previously characterized bianthracene and binaphthalene isomers, 6 isomeric naphthyl-anthracenes were identified. Because of the unavailability of standard reference compounds, structural elucidation was achieved by comparing UV spectral features, mass spectral fragmentation patterns, and GCMS and HPLC elution order with those for bianthracenes, binaphthalenes and other structurally similar molecules. In addition, steric hindrance to rotation at the naphthalene-anthracene bond, a factor that governs the degree of non-planarity of the isomers and thus influences HPLC elution order and MS fragmentation patterns, was estimated using a semi-empirical molecular orbital model.
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