TY - JOUR
T1 - Hydrocarbon Anions with High Stability. Part 2.1} Structure and Stability of Cyclopentadienide Ions with Condensed Aromatic Rings
AU - Kinoshita, Tomomi
AU - Fujita, Masaya
AU - Kaneko, Hideyuki
AU - Takeuchi, Ken'ichi
AU - Yoshizawa, Kazunari
AU - Yamabe, Tokio
N1 - Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.
PY - 1998/5
Y1 - 1998/5
N2 - The ionization-potential and oxidation-potential values have been examined as stability parameters in the gas and solution phase, respectively, for cyclopentadienide ions with from one to four condensed aromatic rings. They indicate that, without solvation effects, the condensed aromatic rings intrinsically stabilize the cyclopentadienide ion in solution as well as in the gas phase, and that an apparent destabilisation effect by the aromatic rings in solution is most probably ascribed to a decrease in the stabilizing solvation effects due to charge delocalization on the carbanions. Theoretical investigations from governing orbital interactions using the frontier orbital theory demonstrate that the essential stability of the cyclopentadienide ions is dependent on the structure, itself.
AB - The ionization-potential and oxidation-potential values have been examined as stability parameters in the gas and solution phase, respectively, for cyclopentadienide ions with from one to four condensed aromatic rings. They indicate that, without solvation effects, the condensed aromatic rings intrinsically stabilize the cyclopentadienide ion in solution as well as in the gas phase, and that an apparent destabilisation effect by the aromatic rings in solution is most probably ascribed to a decrease in the stabilizing solvation effects due to charge delocalization on the carbanions. Theoretical investigations from governing orbital interactions using the frontier orbital theory demonstrate that the essential stability of the cyclopentadienide ions is dependent on the structure, itself.
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U2 - 10.1246/bcsj.71.1145
DO - 10.1246/bcsj.71.1145
M3 - Article
AN - SCOPUS:0005337471
VL - 71
SP - 1145
EP - 1149
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
IS - 5
ER -