Are Antiaromatic Rings Stacked Face-to-Face Aromatic?

The 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)]


Published in:
Organic Letters, 9, 17, 3263-3266
Year:
2007
Keywords:
Note:
CAN 147:364971
22-2
Physical Organic Chemistry
Department of Chemistry and Center for Computational Chemistry,University of Georgia,Athens,GA,USA.
Journal
1523-7060
written in English.
71-43-2 (Benzene); 1120-53-2 (1,3-Cyclobutadiene); 20829-57-6; 29661-18-5 (Cyclopentadienylium); 57266-45-2 (2-Cyclopropylium-1-ylidene); 900180-97-4; 949093-91-8; 949093-93-0 (Hydrocarbon (C24H16); 949093-95-2 (Hydrocarbon (C32H16); 949095-55-0; 949095-56-1; 949095-57-2; 949095-58-3; 949095-59-4 Role: PRP (Properties) (stacking of 4n pi electron hydrocarbon rings into superphane structures)
Laboratories:




 Record created 2007-10-22, last modified 2018-01-28


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