Brunner, Henri and Ikeshita, Masahiro and Tsuno, Takashi (2022) Twofold and Threefold Sinusoidal Patterns in Coupled Molecular Motions of 184,025 Structures of Phenylethane, Nitroethane, and Carboxylate Derivatives. JOURNAL OF ORGANIC CHEMISTRY, 87 (12). pp. 7798-7805. ISSN 0022-3263, 1520-6904
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Scatter plot analyses for 14,169 phenylethanes of the substructure C beta-C alpha H2-Ph with three open coordination positions at C beta and 150,568 phenylethanes of C beta-C alpha HX-Ph with an additional open coordination position X at C alpha have been performed, based on searches in the Cambridge Structural Database. The correlation of rotation angle psi = C beta-C alpha-Ci-Co with a pyramidalization angle theta = Co-Co '-Ci-C alpha in a 360 degrees rotation about the bond C alpha-Ci reveals a sinusoidal pattern with three maxima and minima, whereas the correlation of rotation angle psi with bond angle omega = C beta-C alpha-Ci and bond length d = C beta- C alpha results in sinusoidal patterns with two maxima and minima. A total of 3993 nitro derivatives of the substructure C beta-C alpha HX-NO2 confirm the results and show that atoms Ci/Co/Co ' in the phenyl compounds can be replaced by atoms N/O/O ' without any change in the two- and threefold patterns. In 15,295 methyl acetates of the substructure C beta-C alpha HX-C '(=O)OMe, pyramidalization of the group C alpha C '(=O)OMe results in a chiral flat tetrahedron with four different corners. (R theta)/(S theta) selectivity in the configuration of the tetrahedron is induced by the bonds C alpha-C beta, C alpha-H, and C alpha-X, emanating from the tetrahedral center C alpha. It is surprising that bonds as different as C alpha-C beta, C alpha-H, and C alpha-X (X = H, C, N, O, S, etc.) give almost the same induction intensities.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | 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: | 05 Feb 2024 15:25 |
| Last Modified: | 05 Feb 2024 15:25 |
| URI: | https://pred.uni-regensburg.de/id/eprint/57377 |
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