Correlation Engine 2.0
Clear Search sequence regions

Sizes of these terms reflect their relevance to your search.

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.


Ionel Humelnicu, Ernst-Ulrich Würthwein, Günter Haufe. The conformers of 3-fluoroalanine. A theoretical study. Organic & biomolecular chemistry. 2012 Mar 14;10(10):2084-93

Expand section icon Mesh Tags

Expand section icon Substances

PMID: 22286189

View Full Text