By Shaik S., Shurki A., Danovich D.
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Additional info for A Different Story of pi;-Delocalizations - The Distortivity of pi;-Electrons and Its Chemical Manifestations
Thus, the nuclear motion in the ground state is performed in harmony with the bonding preference of the Kekule´ structures for short double bonds and longer single bonds. Consider now the same vibration starting from the D6h structure of the 1B2u excited state (drawing ii in Figure 20). The excited state’s potential energy surface correlates to the Kekule´ structures with the stretched double bonds. Consequently, motion of the nuclei stretches the double bond and shortens the single bonds. Thus, the b2u mode is forced to occur now in a mismatch with the bonding preference of the Kekule´ constituents, as shown in the right-hand drawing (ii) in Figure 20b using one of Kekule´ structures.
Van Eikema Hommes, N. J. ; Malkin, V. ; Malkina, O. L. J. Am. Chem. Soc. 1997, 119, 12669. (142) P6 was also reported as a ligand in Mo complexes, see: Scherer, O. ; Wolmersha¨user, G. Angew. , Int. Ed. Engl. 1985, 24, 351; Angew. Chem. 1985, 97, 358. ; Hiberty, P. ; Shaik, S. S. Inorg. Chem. 1988, 27, 2219. (144) (a) Borden, W. ; Davidson, E. R. J. Am. Chem. Soc. 1980, 102, 7958; Borden, W. T. J. Am. Chem. Soc. 1975, 97, 5968. ; Rodewald, H. Angew. , Int. Ed. Engl. 1974, 13, 740; Angew. Chem.
1983, 105, 1760. (d) Glukhovtsev, M. ; Schleyer, P. v. R. Chem. Phys. Lett. 1992, 198, 547. ; Huyser, E. S. Borden, W. ; Davidson, E. R. J. Am. Chem. Soc. 1983, 105, 1459. Note that our argument refers to the π-state of formyloxy radical and not to the ground state which is a σ-type radical. ; Davidson, E. ; Borden, W. T. J. Am. Chem. Soc. 1983, 105, 3347. ; Davidson, E. ; Borden, W. T. J. Am. Chem. Soc. 1984, 106, 2513. (c) For a related phenomenon, see: Ayala, P. ; Schlegel, H. B. J. Chem. Phys.
A Different Story of pi;-Delocalizations - The Distortivity of pi;-Electrons and Its Chemical Manifestations by Shaik S., Shurki A., Danovich D.