Highly aromatic planar all-cis-[10]annulene derivatives

Journal Article · Wed Feb 28 04:00:00 EST 1996 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja953126i· OSTI ID:232410

Schleyer, P v.R.; Sulzbach, H M ^[1]; Jiao, H ^[1]; Schaefer, III, H F ^[2]

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1. Universitaet Erlangen-Nuernberg (Germany)
2. Univ. of Georgia, Athens, GA (United States)

Ring strain precludes D{sub 10h} symmetry for the parent [10]-annulene (1). The considerable 10{pi} electron aromaticity of 1 is overwhelmed by the energy required to deform the CCC angles to 144{degree}. We now describe strategies which take advantage of strain to overcome the planarity problem in simple all-cis derivatives of 1. Our ab initio explorations have located and characterized several promising planar 10-membered-ring systems 2-5. Not only the theoretical structures and energies but also the computed magnetic properties demonstrate the considerable aromaticity in these `next higher` analogs of benzene. We now report the structure of 2, and characterize 3-5 computationally. 17 refs., 1 fig., 1 tab.

• DOE Contract Number: FG05-94ER14428
• OSTI ID: 232410
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 8 Vol. 118; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
AROMATICS
BOND ANGLE
BOND LENGTHS
CHEMICAL SHIFT
CYCLOALKENES
MAGNETIC SUSCEPTIBILITY
NMR SPECTRA