{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T10:33:49Z","timestamp":1785407629156,"version":"3.56.0"},"reference-count":34,"publisher":"Beilstein Institut","license":[{"start":{"date-parts":[[2025,9,1]],"date-time":"2025-09-01T00:00:00Z","timestamp":1756684800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2025,9,1]],"date-time":"2025-09-01T00:00:00Z","timestamp":1756684800000},"content-version":"am","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2025,9,1]],"date-time":"2025-09-01T00:00:00Z","timestamp":1756684800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"name":"JSPS KAKENHI","award":["C 23K04755"],"award-info":[{"award-number":["C 23K04755"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Beilstein J. Org. Chem."],"accepted":{"date-parts":[[2025,8,12]]},"abstract":"<jats:p>\n                    In single crystals of C\u2013N atropisomeric\n                    <jats:italic>N<\/jats:italic>\n                    -(2-halophenyl)quinolin-2-one and the thione analogue, a unique association based on a halogen\u2013\u03c0 interaction was detected. In racemic and optically pure\n                    <jats:italic>N<\/jats:italic>\n                    -(2-bromo- or 2-chlorophenyl)quinolin-2-ones, homochiral layered polymers, which consist of (\n                    <jats:italic>P<\/jats:italic>\n                    )- or (\n                    <jats:italic>M<\/jats:italic>\n                    )-atropisomers, were formed through intermolecular halogen\u2013\u03c0 association. The halogen\u2013\u03c0 association in the racemates is due to a halogen bond (C\u2013X\u00b7\u00b7\u00b7\u03c0) between a \u03c3-hole on the halogen atom and a \u03c0-electron on the quinolinone benzene ring, while that in optically pure forms is caused by an n\u2013\u03c0* interaction between a lone electron pair on the halogen atom and a \u03c0* orbital of the quinolinone. In contrast to the formation of the homochiral layered polymer in quinolinones, in racemic\n                    <jats:italic>N<\/jats:italic>\n                    -(2-bromophenyl)quinoline-2-thione, heterochiral layered polymers, in which (\n                    <jats:italic>P<\/jats:italic>\n                    )- and (\n                    <jats:italic>M<\/jats:italic>\n                    )-atropisomers were alternately connected, were formed through an n\u2013\u03c0* interaction between a lone electron pair on the bromine atom and a \u03c0* orbital of the quinoline-2-thione.\n                  <\/jats:p>","DOI":"10.3762\/bjoc.21.138","type":"journal-article","created":{"date-parts":[[2025,9,1]],"date-time":"2025-09-01T08:02:20Z","timestamp":1756713740000},"page":"1748-1756","source":"Crossref","is-referenced-by-count":3,"title":["Unique halogen\u2013\u03c0 association detected in single crystals of C\u2013N atropisomeric\n                    <i>N<\/i>\n                    -(2-halophenyl)quinolin-2-one derivatives and the thione 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