Ab initio calculations of molecular and electronic structures of neutr
al molecules and protonated forms of methionine and its derivatives in
the gaseous phase were carried out by the Hartree-Fock method using t
he 6-31G basis set with full geometry optimization. Proton affinities
of methionine (1), methionine sulfoxide (2), and methionine sulfone (
3) were calculated for different modes of coordination of the proton.
The results of calculations demonstrated that in protonated forms of 1
and 3, bonding between the proton and the N atom is most favorable, w
hile in protonated form of 2, bonding between the proton and the O ato
m of the SO group is most favorable. The proton affinities of the amin
o acids are as follows: 223.2 (1), 241.2 (2), and 221.5 (3) kcal mol(-
1), i.e., methionine sulfoxide 2 exhibits the highest proton affinity
in the series of the amino acids under consideration.