sigma*-aromaticity in three-membered rings
Göller AH, Clark T (2000)
Publication Status: Published
Publication Type: Journal article
Publication year: 2000
Journal
Publisher: Springer Verlag (Germany)
Book Volume: 6
Pages Range: 133-149
Journal Issue: 2
DOI: 10.1007/PL00010724
Abstract
The geometrical changes in bond lengths and angles, which correlate with substituent electronegativities, are discussed for the different ring systems. The relative stabilities of unsaturated and saturated rings are compared using isodesmic ring-opening reactions and homodesmic substituent-exchange reactions. sigma*-Aromaticity, a hyperconjugative effect found in the disubstituted rings, causes lowering of ring strain energies for the unsaturated rings and preference of unsaturated rings over saturated ones for the more electronegative substituents. For the mono-substituted pi-aromatic silacyclopropenes and cyclopropenes, a destabilization by more electronegative ligands is found. For the neutral rings monosubstituted at main group V atoms like the 1H-phosphirenes and also the isoelectronic negatively charged rings with main group IV atoms like the silacyclopropenium anions, no correlation of stabilization energies or geometrical changes with ligand electronegativity is found.
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Germany (DE)How to cite
APA:
Göller, A.H., & Clark, T. (2000). sigma*-aromaticity in three-membered rings. Journal of Molecular Modeling, 6(2), 133-149. https://dx.doi.org/10.1007/PL00010724
MLA:
Göller, Andreas H., and Timothy Clark. "sigma*-aromaticity in three-membered rings." Journal of Molecular Modeling 6.2 (2000): 133-149.
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