title: The conformers of 3-fluoroalanine. A theoretical study.
abstract: Quantum chemical calculations (DFT, SCS-MP2) show that the relative energies of the four principal alanine conformations are only marginally altered by the introduction of a single fluorine substituent into the methyl group. The fluorine gauche effect and attractive interactions of fluorine to the O-H or N-H moieties (formation of hydrogen bridges) do stabilize particular conformers of 3-fluoroalanine. This is true for the neutral molecule both in the gas phase and in aqueous solution (CPCM-model), but also for the zwitterionic forms and the conformers of the related carboxylate ions and also for the respective ammonium ions in aqueous solution. In water (CPCM calculations), the zwitterion is almost equal in energy to the most stable conformer of the neutral 3-fluoroalanine. Compared to alanine the atomic charges of the amino group and the carboxyl function of 3-fluoroalanine are not significantly influenced by the fluorine at C3, which relates to the fact that both experimental pK(a) values are almost equal for alanine and 3-fluoroalanine.
authors.affiliation: Organisch Chemisches Institut, Universität Münster, Corrensstr. 40, D-48149 Münster, Germany. ionel@uaic.ro
authors.forename: Ionel
authors.initials: I
authors.lastname: Humelnicu
authors.forename: Ernst-Ulrich
authors.initials: EU
authors.lastname: Würthwein
authors.forename: Günter
authors.initials: G
authors.lastname: Haufe
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D005740:Gases / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D011522:Protons; D011789:Quantum Theory; D014867:Water / Q000737:chemistry
chemical_list: D005740:Gases; D011522:Protons; D014867:Water; D005461:Fluorine; C007742:3-fluoroalanine; D000409:Alanine