By Zvi Rappoport, Yitzhak Apeloig
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3H2 XDXH2 C 3H3 X XH3 X D C; Si (15) In the context of the question of the aromaticity of Si6 H6 , special attention should be paid to the recent studies by Shaik and coworkers15 . e. E and E , respectively), they reached the following conclusions: (a) The geometry is not a proper measure of aromaticity. e. if E C E > 0, the structure is dictated by the symmetric -skeleton and it is delocalized. The localizing propensity of the -electrons is dependent on the singlet triplet energy gap of the -bond and consequently on its strength.
Similar behaviour was observed for the H2 XDXH2 series, where X D Si65,66 , Ge, Sn and Pb66,62 . e. the ASEs calculated according to equation 14a for 62 X6 H6 (X D Si, Ge, Sn and Pb) are all in the range of 9 12 kcal mol 1 . 8 kcal mol 1 at MP2/ECP(d)//HF/ECP(d)]53a , indicating the small effect of substituting three Si atoms in Si6 H6 by C or Ge. 9). The stability of the Dewar benzene (34) and the benzvalene (35) isomers relative to the corresponding aromatic D6h X6 H6 isomer also increases along the series X D C !
68 8 d d e 11g 14a 14b 17 16 a ASE(silabenzenoid)/ASE(benzene). b The number in the text of the homodesmotic equation used to evaluate ASE. 7 ppm for 8 and benzene, respectively8 . d According to the equation: 22 (or 11) C 2SiH C 4CH ! 2H SiDCH C C H C C H C 2H CSiH . 4 4 2 2 2 4 2 6 3 3 e According to the equation: 21 C 2SiH C 4CH ! H SiDSiH C C H C C H C 2H CSiH . 4 4 2 2 2 4 2 6 3 3 f Resonance energy (RE); ASE is not reported. g The RE of benzene was calculated from equation 2. 8 ppm for 31 and benzene, respectively19 .
The Chemistry of Organic Silicon Compounds by Zvi Rappoport, Yitzhak Apeloig