Möbius aromaticity

A monocyclic array of orbitals in which there is a single out-of-phase overlap (or, more generally, an odd number of out-of-phase overlaps) reveals the opposite pattern of aromatic character to Hückel systems; with 4n electrons it is stabilized (aromatic), whereas with 4n + 2 it is destabilized (antiaromatic). In the excited state 4n + 2 Möbius π-electron systems are stabilized, and 4n systems are destabilized. No examples of ground-state Möbius π-electron systems are known, but the concept has been applied to transition states of pericyclic reactions. The name is derived from the topological analogy of such an arrangement of orbitals to a Möbius strip.
See: aromatic
See also: Hückel (4n + 2) rule
PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1141 (https://doi.org/10.1351/pac199466051077)