Temporary anion states of selected amino acids

Vertical attachment energies for the formation of low-lying temporary anion states of glycine, alanine, phenylalanine, tryptophan, and proline in the gas phase are reported using, electron transmission spectroscopy. Electron attachment into the empty pi* orbital of the -COOH group was observed in all the compounds. Temporary anion states associated with the side groups in phenylalanine and tryptophan are found to be stabilized with respect to those in the reference compounds toluene and indole, respectively, by approximately 0.2 eV. We attribute this to electrostatic effects and explore, using simple theoretical models, the extent to which such anion states could be further stabilized if these amino acids were in zwitterionic form. (C) 2001 American Institute of Physics.