Corminboeuf, ClemenceSchleyer, Paul von R.Warner, Philip2007-10-222007-10-222007-10-22200710.1021/ol071183yhttps://infoscience.epfl.ch/handle/20.500.14299/13205The stacking of 4n pi electron hydrocarbon rings into superphane structures can eliminate their antiaromaticity and result in through-space three-dimensional arom. character. This is demonstrated by the bond length equalized geometries and diatropic NICS values of the methano-bridged superphane series with interacting three- to nine-membered 4n pi electron rings. Along with triplet and Moebius strategies, stacking is the third way to achieve arom. ring systems with 4n pi electrons. [on SciFinder (R)]LUMO (HOMO gap; stacking of 4n pi electron hydrocarbon rings into superphane structures); HOMO (LUMO gap; stacking of 4n pi electron hydrocarbon rings into superphane structures); Aromaticity (NICS; stacking of 4n pi electron hydrocarbon rings into superphane structures); Molecular structure (optimized; stacking of 4n pi electron hydrocarbon rings into superphane structures); Antiaromaticity; Energy (stacking of 4n pi electron hydrocarbon rings into superphane structures); Pi-pi interaction (stacking; stacking of 4n pi electron hydrocarbon rings into superphane structures)antiarom ring stacked face to face arom B3LYPtext::journal::journal article::research article