fluoratomer

Fluoratomer is a term used in some chemical discussions to describe a family of interconvertible fluorinated forms of a molecule, in which the fluorine substituent occupies different positions on the carbon framework. The concept is similar to tautomerism or regioisomerism, but specific to fluorine-bearing compounds where the fluorine can migrate or be rearranged between sites within the same molecule. In practice, fluoratomerism can arise from rapid intramolecular exchange processes such as SN2-like fluoride shifts, [1,2]-fluorine migrations, or prototropic shifts that involve halogen transfer, often mediated by acids, bases, or neighboring heteroatoms. When the exchange is fast on the NMR timescale, the different fluorinated forms are observed as a single averaged signal; at low temperatures or in the presence of stabilizing interactions, multiple fluoratomer forms may be observed.

The term is not part of standard IUPAC nomenclature and is used mainly in discussions of dynamic behavior of fluorinated molecules or in speculative or introductory texts. In typical usage, researchers would instead describe the system in terms of selected fluorine positions, regioisomerism, or tautomerism, and would specify the conditions under which distinct species can be observed. Examples include cases where fluorine migration affects reactivity, such as in oxidative fluorination products or in fluorinated enolates.

Further study usually involves NMR, mass spectrometry, and computational methods to determine the energy landscape of possible fluorinated forms and the barriers to interconversion.