Zusammenfassung
In this study we investigate the pyramidalization of the sp(2)-hybridized center at the ipso-carbon atom C-i of phenyl compounds on the theoretical side by DFT calculations of toluene, t-butylbenzene, and ethylbenzene and on the experimental side by a scatter plot analysis of 14,169 structures of ethylbenzene compounds C-& beta;-C & alpha;H2-C6H5 with three open positions for variation at C-& ...
Zusammenfassung
In this study we investigate the pyramidalization of the sp(2)-hybridized center at the ipso-carbon atom C-i of phenyl compounds on the theoretical side by DFT calculations of toluene, t-butylbenzene, and ethylbenzene and on the experimental side by a scatter plot analysis of 14,169 structures of ethylbenzene compounds C-& beta;-C & alpha;H2-C6H5 with three open positions for variation at C-& beta;, accumulated in the Cambridge Structural Database. In a 360 & DEG; rotation about the bond between C-& alpha; of the substituent and the ipso-carbon atom C-i of the phenyl ring, the pyramidalization performs three maxima and minima. A comparison of structures with pyramidalization and its hypothetical counterparts without pyramidalization shows that pyramidalization is associated with a gain of energy. The data reveal that it is the carbon atom C-& alpha; of the phenyl substituent, which on pyramidalization bends away from the phenyl plane. Pyramidalization of sp(2)-hybridized centers is an omnipresent member in molecular weak interactions.
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