Proton affinities and gas-phase basicities of glycine, serine and cysteine have been computed using the three-parameter B3LYP density functional approach. For that, the geometry and vibrational frequencies of several conformations of neutral and protonated glycine, serine and cysteine have been explored. The preferred site for protonation in all aminoacids is the amino group. The lowest conformation always shows an intramolecular hydrogen bond between NH3+ and the carbonylic oxygen. For serine and cysteine, additional hydrogen bonds may be formed, the favored interaction being that in which the oxygen or sulfur atoms of the side chain interact, as proton acceptor, with NH3+. The computed B3LYP proton affinities and gas-phase basicities are in very good agreement with the known experimental data. © 2001 Elsevier Science B.V.
|Journal||Journal of Molecular Structure: THEOCHEM|
|Publication status||Published - 12 Mar 2001|
- Proton affinities