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Studies on rotational barriers of N-C axially chiral compounds: increase in the rotational barrier by aromatization |
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| Authors: | Naomi SuzumuraMasato Kageyama Daichi KamimuraTakahiro Inagaki Yasuo DobashiHiroshi Hasegawa Haruhiko FukayaOsamu Kitagawa |
| Institution: | a Department of Applied Chemistry, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan b School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan |
| Abstract: | The rotational barriers in axially chiral quinolin-2-one and quinazolin-2-one possessing N-(ortho-tert-butyl)phenyl group were found to significantly increase in comparison with those of corresponding dihydroquinolin-2-one and dihydroquinazolin-2-one. Analysis of transition state structure during N-Ar bond rotation based on DFT calculation indicates that the increase in the rotational barrier is due to considerable distortion of the nitrogen-containing heterocyclic part. |
| Keywords: | Axially chiral Aromatization Quinolinone Quinazolinone Rotational barrier |
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