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 @A00441@ character to Hückel systems; with \(4\, n\) electrons it is stabilized (aromatic), whereas with \(4\, n+2\) it is destabilized (antiaromatic). In the @E02257@ \(4\, n+2\) Möbius π-electron systems are stabilized, and \(4\, n\) systems are destabilized. No examples of ground-state Möbius π-electron systems are known, but the concept has been applied to @T06468@ of @P04491@. The name is derived from the topological analogy of such an arrangement of orbitals to a Möbius strip.
See also:
Hückel (4n + 2) rule
PAC, 1994, 66, 1077. (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1141 [Terms] [Paper]