Brunner, Henri and Ikeshita, Masahiro and Tsuno, Takashi (2023) Pyramidalization at the sp2-Hybridized ipso-Carbon Atom of Phenyl Compounds. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 26 (36). ISSN 1434-193X, 1099-0690
Full text not available from this repository. (Request a copy)Abstract
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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | AB-INITIO; DENSITY; ENVIRONMENTS; ATTRACTION; DFT; sp(2)-hybridized centers; gain of energy; ipso-carbon atom; phenyl compounds; pyramidalization |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Henri Brunner |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 12 Mar 2024 09:51 |
| Last Modified: | 12 Mar 2024 09:51 |
| URI: | https://pred.uni-regensburg.de/id/eprint/59694 |
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