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The UV photoelectron spectra of adenine, 9-methyladenine, and 6-methylaminopurine contain highly resolved bands arising from the six highest occupied molecular orbitals. The spectra have been analyzed using UV absorption data, photoelectron data from previous studies of heterocyclic compounds, and results from both semi-empirical and ab initio molecular orbital calculations. The analysis indicates that the first, third, and fifth photoelectron bands in adenine and the two methyl substituted derivatives arise from pi orbitals. The second, fourth, and sixth bands arise from nitrogen atom lone-pair orbitals. Compared to adenine, the six uppermost orbitals of 9-methyladenine and 6-methylaminopurine have lower ionization potentials. This destabilization of the valence electrons is expected to play an important role in causing the increase in base stacking forces observed in methyl substituted adenines.

Ultraviolet photoelectron studies of biological purines: the valence electronic structure of adenine.