By Shaik S., Shurki A., Danovich D.
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Extra resources for A Different Story of pi;-Delocalizations - The Distortivity of pi;-Electrons and Its Chemical Manifestations
N. ; Masamune, S. J. Am. Chem. Soc. 1975, 97, 1973. ; Masamune, S. Tetrahedron 1980, 36, 343. The first unequivocal assignment of rectangular singlet cyclobutadiene by theory was reported by Buenker and Peyerimhoff, see: Buenker, R. ; Peyerimhoff, S. D. J. Chem. Phys. 1968, 48, 354. ; Chu, W. J. Am. Chem. Soc. 1970, 92, 2165. Breslow, R. Acc. Chem. Res. 1973, 6, 393. ; Mohacsi, E. J. Am. Chem. Soc. 1963, 85, 431. (a) Dewar, M. J. ; Gleicher, G. J. J. Am. Chem. Soc. 1965, 87, 685. (b) Dewar, M. J.
3 1. E) of naphthalene are shown in Scheme 36a. Two of them are designated as K1 and K2 and represent the annulenic resonance along the perimeter of the naphthalene, while the third one, Kc, has a double bond in the center and transforms as the totally symmetric irreducible representation, Ag of the D2h group. The K1 and K2 structures are mutually interchangeable by the i, C2, and σv symmetry operations of the point group, much as in the case of benzene. An in-phase combination transforms, therefore, as Ag, whereas an out-of-phase one transforms as B2u.
S. J. Am. Chem. Soc. 1995, 117, 2102. (172) Deniz, A. ; Peters, K. ; Snyder, G. J. Science 1999, 286, 1119. ; Shaik, S. Chem. Phys. Lett. 1998, 292, 7-14. (b) Wu. ; Shaik, S. J. Phys. Chem. A. 2000, 104, 8744. (174) For an illuminating discussion of the negative DRE(cb) and its critique, see ref 78. See also: Bauld, N. ; Welsher, T. ; Holloway, R. L. J. Am. Chem. Soc. 1978, 100, 6920. (175) Garratt, P. J. Aromaticity; Wiley: New York, 1986. 4 kcal/mol for the bond shift in the planar COT. 4 kcal/mol for the bond shift in the planar COT.