@article{cab794093bf14e20b36c3fa5a7e6a65a,
title = "Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one",
abstract = "The rotational barrier around the N-C chiral axis in N-(2-tert-butylphenyl)-3,4-dihydrobenzoquinolin-2-one was found to be 6 kcal/mol lower than that in N-(2-tert-butylphenyl)-3,4-dihydroquinolin-2-one. X-ray crystal structures and 1H NMR spectra of both compounds indicate that the significant decrease in the rotational barrier in benzoquinolinone is brought about by destabilization of the ground state which is highlighted by a considerable distortion of the N-C chiral axis.",
keywords = "Amination, Axially chiral, Distortion, Quinolinone, Rotational barrier",
author = "Yuya Suzuki and Isao Takahashi and Yasuo Dobashi and Hiroshi Hasegawa and Christian Roussel and Osamu Kitagawa",
note = "Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",
year = "2015",
month = jan,
day = "1",
doi = "10.1016/j.tetlet.2014.11.040",
language = "English",
volume = "56",
pages = "132--135",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "1",
}