Sigma-antiaromaticity in cyclobutane,cubane, and other molecules with saturated four-membered rings |
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Authors: | Moran Damian Manoharan Mariappan Heine Thomas Schleyer Paul von Ragué |
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Institution: | Computational Chemistry Annex, University of Georgia, Athens, GA 30602, USA. |
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Abstract: | Dissected nucleus-independent chemical shift (NICS) analyses of cycloalkanes and cage hydrocarbons reveal contrasting ring current effects, diatropic in three- and five-membered and paratropic in four-membered ring systems. The large shielding effects of the C-C bonds of the archetypal sigma-aromatic, cyclopropane, are magnified in tetrahedrane and related structures. The remarkable deshielding effect of the cyclobutane C-C(sigma) bonds is general: cubane and cages with four-membered rings are strongly deshielding (i.e., sigma-antiaromatic).structure--see text] |
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