{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T12:23:30Z","timestamp":1787228610727,"version":"build-2736575974"},"reference-count":52,"publisher":"American Chemical Society (ACS)","issue":"33","license":[{"start":{"date-parts":[[2027,8,5]],"date-time":"2027-08-05T00:00:00Z","timestamp":1817424000000},"content-version":"vor","delay-in-days":365,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T00:00:00Z","timestamp":1785888000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T00:00:00Z","timestamp":1785888000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T00:00:00Z","timestamp":1785888000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP24K15167"],"award-info":[{"award-number":["JP24K15167"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,20]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\u03c0\/\u03c0, CH\/\u03c0, and halogen\/\u03c0 interactions are key intermolecular interactions in molecular design for drug discovery and materials science. Three-dimensional (3D) characterization of these interactions is essential for rational molecular design, as molecules typically form noncovalent interactions in multiple directions within complex systems. Accordingly, 3D descriptions of \u03c0\/\u03c0, CH\/\u03c0, and halogen\/\u03c0 interactions provide valuable insights for rational molecular design. In this study, we present experimentally and theoretically validated 3D descriptions of interaction-formable regions for \u03c0\/\u03c0, CH\/\u03c0, and halogen\/\u03c0 interactions around phenyl and halogenated phenyl substructures, based on quantum mechanical molecular interaction field (MIF(QM)) calculations and database analyses. O-shaped or C-shaped \u03c0\/\u03c0 interaction regions are observed above and below the aromatic rings of benzene and halobenzene molecules. Halogen substitution enhances the stability of \u03c0\/\u03c0 interactions by 1.0\u20132.5 kcal\/mol. Spherical CH\/\u03c0 interaction regions are located beyond the \u03c0\/\u03c0 interaction regions, which are more spatially extended than those of CH\/\u03c0 interactions. In addition, halogen\/\u03c0 and CH\/\u03c0 interaction regions are distributed along the extension lines of C\u2013X (X = Cl, Br, I) and C\u2013H bonds, respectively. The proposed 3D descriptions of \u03c0\/\u03c0, CH\/\u03c0, and halogen\/\u03c0 interactions provide a framework for understanding and predicting molecular recognition in protein\u2013ligand systems.<\/jats:p>","DOI":"10.1021\/acs.jpcb.6c03632","type":"journal-article","created":{"date-parts":[[2026,8,6]],"date-time":"2026-08-06T02:02:21Z","timestamp":1785981741000},"page":"8395-8408","source":"Crossref","is-referenced-by-count":0,"title":["Three-Dimensional\nDescriptions of \u03c0\/\u03c0,\nCH\/\u03c0, and Halogen\/\u03c0 Interactions Formed between Phenyl\nSubstructures"],"prefix":"10.1021","volume":"130","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1942-2492","authenticated-orcid":true,"given":"Daichi","family":"Hayakawa","sequence":"first","affiliation":[{"name":"Showa Medical University Graduate School of Pharmacy , , 1-5-8, Hatanodai , Shinagawa-ku, ,","place":["Tokyo, Japan, 142-8555"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroaki","family":"Gouda","sequence":"additional","affiliation":[{"name":"Showa Medical University Graduate School of Pharmacy , , 1-5-8, Hatanodai , Shinagawa-ku, ,","place":["Tokyo, Japan, 142-8555"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,5]]},"reference":[{"key":"2026082007204208800_cit1","doi-asserted-by":"publisher","first-page":"5525","DOI":"10.1021\/ja00170a016","article-title":"The nature of \u03c0-\u03c0 interactions","volume":"112","author":"Hunter","year":"1990","journal-title":"J. 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Theory Comput."},{"key":"2026082007204208800_cit52","doi-asserted-by":"publisher","first-page":"5063","DOI":"10.1021\/ja00383a012","article-title":"Crystallographic evidence\nfor the existence of C-H\u00b7\u00b7\u00b7O,\nC-H\u00b7\u00b7\u00b7N, and C-H\u00b7\u00b7\u00b7Cl hydrogen bonds","volume":"104","author":"Taylor","year":"1982","journal-title":"J. Am. Chem. 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