{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T20:45:17Z","timestamp":1791924317015,"version":"4.3.4"},"reference-count":106,"publisher":"American Chemical Society (ACS)","issue":"40","license":[{"start":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T00:00:00Z","timestamp":1790553600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100010265","name":"Guizhou Medical University","doi-asserted-by":"publisher","award":["22NSFCP35"],"award-info":[{"award-number":["22NSFCP35"]}],"id":[{"id":"10.13039\/501100010265","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010265","name":"Guizhou Medical University","doi-asserted-by":"publisher","award":["J[2021]039"],"award-info":[{"award-number":["J[2021]039"]}],"id":[{"id":"10.13039\/501100010265","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100013078","name":"Natural Science Research Project of Guizhou Province","doi-asserted-by":"publisher","award":["ZK[2023]294"],"award-info":[{"award-number":["ZK[2023]294"]}],"id":[{"id":"10.13039\/501100013078","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100013078","name":"Natural Science Research Project of Guizhou Province","doi-asserted-by":"publisher","award":["ZK[2024]145"],"award-info":[{"award-number":["ZK[2024]145"]}],"id":[{"id":"10.13039\/501100013078","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22263003"],"award-info":[{"award-number":["22263003"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Guizhou Key Laboratory of Microbio and Infectious Disease Prevention and Control","award":["ZDSYS[2023]004"],"award-info":[{"award-number":["ZDSYS[2023]004"]}]},{"name":"Central Government Guided Local Science Foundation of Guizhou Province","award":["Qiankehe[2025]024"],"award-info":[{"award-number":["Qiankehe[2025]024"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,13]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Chalcogen bonds (ChBs), a prominent subclass of \u03c3-hole interactions in which Group 16 elements serve as electrophilic sites, have attracted considerable attention in recent years because of their pivotal roles in diverse chemical and biological systems. However, the combined influence of the chalcogen atomic size and the nitrogen atomic hybridization state on the nature and strength of chalcogen\u00b7\u00b7\u00b7nitrogen (Ch\u00b7\u00b7\u00b7N) interactions remains underexplored. Herein, \u03c3-hole-type Ch\u00b7\u00b7\u00b7N ChBs formed between 2,2,4,4-tetrafluoro-1,3-dichalcogenetanes (C2F4Ch2, Ch = S, Se, Te, Po) and nitrogen bases with distinct hybridization patterns (sp-NCH, sp2-NH\u2550CH2, sp2-pyridine, sp3-NH3) are systematically investigated using quantum chemical calculations. The computed interaction energies vary from \u221216.8 to \u221262.5 kJ\/mol. The two moieties are held together primarily through the Ch\u00b7\u00b7\u00b7N ChBs. These ChBs show substantial bond contraction, with Ch\u00b7\u00b7\u00b7N distances approximately 12\u201329% shorter than the sum of the respective van der Waals radii. Topological analysis indicates that although most Ch\u00b7\u00b7\u00b7N ChBs exhibit noncovalent closed-shell characteristics, Te\/Po\u00b7\u00b7\u00b7N ChBs in complexes with NH3, NH\u2550CH2, or pyridine display a partially covalent nature. Notably, the Ch\u00b7\u00b7\u00b7N ChB strength typically increases in the order Ch = S &amp;lt; Se &amp;lt; Po &amp;lt; Te and follows the nitrogen base sequence: NCH (sp) &amp;lt; NH3 (sp3) &amp;lt; NH\u2550CH2 (sp2) &amp;lt; pyridine (sp2). Natural bond orbital (NBO) analysis suggests that the predominant orbital interaction associated with the Ch\u00b7\u00b7\u00b7N ChB involves charge transfer from the nitrogen lone pair into the \u03c3*(C\u2013Ch) antibonding orbitals. Energy decomposition analysis reveals that electrostatic interactions provide the largest attractive contribution to the stabilization of these chalcogen-bonded complexes. These findings provide critical insights into the tunability of chalcogen bonding interactions by modulating the atomic and electronic structures of the interacting partners.<\/jats:p>","DOI":"10.1021\/acsomega.6c07591","type":"journal-article","created":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T03:02:31Z","timestamp":1790650951000},"page":"61751-61766","source":"Crossref","is-referenced-by-count":0,"title":["Tuning \u03c3-Hole\nChalcogen\u00b7\u00b7\u00b7Nitrogen\nBonding Between C2F4Ch2 and Nitrogen\nBases: Dual Modulation by Chalcogen Atomic Size and Nitrogen Hybridization\n(Ch = S, Se, Te, Po)"],"prefix":"10.1021","volume":"11","author":[{"given":"Ke","family":"Peng","sequence":"first","affiliation":[{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fengying","family":"Lei","sequence":"additional","affiliation":[{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Renhua","family":"Chen","sequence":"additional","affiliation":[{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Taowang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junhua","family":"Chen","sequence":"additional","affiliation":[{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinxi","family":"Huang","sequence":"additional","affiliation":[{"name":"Chongqing University , , Daxuecheng South Rd. 55 , ,","place":["Chongqing, China, 401331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qingyu","family":"Liu","sequence":"additional","affiliation":[{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]},{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8631-7671","authenticated-orcid":true,"given":"Gang","family":"Feng","sequence":"additional","affiliation":[{"name":"Chongqing University , , Daxuecheng South Rd. 55 , ,","place":["Chongqing, China, 401331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zuquan","family":"Hu","sequence":"additional","affiliation":[{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]},{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3589-9437","authenticated-orcid":true,"given":"Tao","family":"Lu","sequence":"additional","affiliation":[{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]},{"name":"Guizhou Medical University , , Guian New District, ,","place":["Guiyang, China, 561113"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,28]]},"reference":[{"key":"2026101315090506500_cit1","doi-asserted-by":"publisher","first-page":"11178","DOI":"10.1039\/c3cp00054k","article-title":"Halogen bonding and other \u03c3-hole\ninteractions: A perspective","volume":"15","author":"Politzer","year":"2013","journal-title":"Phys. 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Rev."},{"key":"2026101315090506500_cit4","doi-asserted-by":"publisher","first-page":"5072","DOI":"10.1021\/acs.chemrev.5b00527","article-title":"\u03c3-Hole bond\nvs \u03c0-hole\nbond: A comparison based on halogen bond","volume":"116","author":"Wang","year":"2016","journal-title":"Chem.\nRev."},{"key":"2026101315090506500_cit5","doi-asserted-by":"publisher","first-page":"212","DOI":"10.3390\/cryst7070212","article-title":"\u03c3-Hole interactions: Perspectives and misconceptions","volume":"7","author":"Politzer","year":"2017","journal-title":"Crystals"},{"key":"2026101315090506500_cit6","doi-asserted-by":"publisher","first-page":"291","DOI":"10.1007\/s00894-006-0130-2","article-title":"Halogen bonding: the\n\u03c3-hole: proceedings of \u201cModeling interactions in biomolecules\nII\u201d, Prague, September 5th\u20139th, 2005","volume":"13","author":"Clark","year":"2007","journal-title":"J. Mol. Model."},{"key":"2026101315090506500_cit7","doi-asserted-by":"publisher","first-page":"723","DOI":"10.1007\/s00894-008-0386-9","article-title":"Expansion of the \u03c3-hole\nconcept","volume":"15","author":"Murray","year":"2009","journal-title":"J. Mol. Model."},{"key":"2026101315090506500_cit8","doi-asserted-by":"publisher","first-page":"13","DOI":"10.1002\/wcms.1113","article-title":"\u03c3-Holes\nWIREs Comput","volume":"3","author":"Clark","year":"2013","journal-title":"Mol. Sci."},{"key":"2026101315090506500_cit9","doi-asserted-by":"publisher","first-page":"1411","DOI":"10.1039\/D2CE01621D","article-title":"Definition\nof the tetrel bond","volume":"25","author":"Varadwaj","year":"2023","journal-title":"CrystEngComm"},{"key":"2026101315090506500_cit10","doi-asserted-by":"publisher","first-page":"149","DOI":"10.3390\/inorganics10100149","article-title":"Definition\nof the pnictogen bond: A perspective","volume":"10","author":"Varadwaj","year":"2022","journal-title":"Inorganics"},{"key":"2026101315090506500_cit11","doi-asserted-by":"publisher","first-page":"1889","DOI":"10.1515\/pac-2018-0713","article-title":"Definition of the chalcogen bond\n(IUPAC Recommendations 2019)","volume":"91","author":"Aakeroy","year":"2019","journal-title":"Pure Appl. Chem."},{"key":"2026101315090506500_cit12","doi-asserted-by":"publisher","first-page":"15160","DOI":"10.1021\/jacs.7b08511","article-title":"The origin\nof chalcogen-bonding interactions","volume":"139","author":"Pascoe","year":"2017","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026101315090506500_cit13","doi-asserted-by":"publisher","first-page":"1711","DOI":"10.1351\/PAC-REC-12-05-10","article-title":"Definition\nof the halogen bond (IUPAC Recommendations 2013)","volume":"85","author":"Desiraju","year":"2013","journal-title":"Pure Appl. Chem."},{"key":"2026101315090506500_cit14","doi-asserted-by":"publisher","first-page":"2478","DOI":"10.1021\/acs.chemrev.5b00484","article-title":"The halogen bond","volume":"116","author":"Cavallo","year":"2016","journal-title":"Chem. Rev."},{"key":"2026101315090506500_cit15","doi-asserted-by":"publisher","first-page":"7340","DOI":"10.1002\/anie.201502571","article-title":"Aerogen bonding interaction: A new\nsupramolecular force?","volume":"54","author":"Bauza\u0301","year":"2015","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101315090506500_cit16","doi-asserted-by":"publisher","first-page":"1205","DOI":"10.3390\/cryst11101205","article-title":"On the importance\nof \u03c3-hole interactions in crystal\nstructures","volume":"11","author":"Frontera","year":"2021","journal-title":"Crystals"},{"key":"2026101315090506500_cit17","doi-asserted-by":"publisher","first-page":"731","DOI":"10.1016\/j.chempr.2018.02.022","article-title":"Sigma-hole interactions in anion recognition","volume":"4","author":"Lim","year":"2018","journal-title":"Chem"},{"key":"2026101315090506500_cit18","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1007\/978-3-031-00657-9_7","article-title":"Supramolecular\nassemblies based on \u03c3-hole interactions","volume-title":"Supramolecular Assemblies Based on Electrostatic Interactions","author":"Bauza\u0301","year":"2022"},{"key":"2026101315090506500_cit19","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202404823","article-title":"Halogen, chalcogen, pnictogen, and\ntetrel bonding in non-covalent organocatalysis: An update","volume":"63","author":"Jovanovic","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101315090506500_cit20","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202300026","article-title":"Non-classical non-covalent \u03c3-hole\ninteractions in protein structure and function: Concepts for potential\nprotein engineering applications","volume":"18","author":"Walker","year":"2023","journal-title":"Chem. - Asian\nJ."},{"key":"2026101315090506500_cit21","doi-asserted-by":"publisher","first-page":"2514","DOI":"10.1021\/ar5001555","article-title":"Halogen bonds in\ncrystal engineering:\nLike hydrogen bonds yet different","volume":"47","author":"Mukherjee","year":"2014","journal-title":"Acc. Chem.\nRes."},{"key":"2026101315090506500_cit22","doi-asserted-by":"crossref","first-page":"143","DOI":"10.5772\/48592","article-title":"Halogen bonding\nin crystal engineering","volume-title":"Recent Advances\nin Crystallography","author":"Ding","year":"2012"},{"key":"2026101315090506500_cit23","doi-asserted-by":"publisher","first-page":"216488","DOI":"10.1016\/j.ccr.2025.216488","article-title":"Halogen bonding\nin supramolecular chemistry: From molecular\ncomponents to assembled structures","volume":"530","author":"Liu","year":"2025","journal-title":"Coord. Chem.\nRev."},{"key":"2026101315090506500_cit24","doi-asserted-by":"publisher","first-page":"4970","DOI":"10.1039\/D0CC00841A","article-title":"Halogen bonding for molecular recognition:\nNew developments in materials and biological sciences","volume":"56","author":"Berger","year":"2020","journal-title":"Chem. Commun."},{"key":"2026101315090506500_cit25","doi-asserted-by":"publisher","first-page":"214556","DOI":"10.1016\/j.ccr.2022.214556","article-title":"Chalcogen bonding in coordination\nchemistry","volume":"464","author":"Mahmudov","year":"2022","journal-title":"Coord. Chem. Rev."},{"key":"2026101315090506500_cit26","doi-asserted-by":"publisher","first-page":"217416","DOI":"10.1016\/j.ccr.2025.217416","article-title":"Chalcogen bonding in complexes based\non electrophilic\ntellurium","volume":"551","author":"Hernandez","year":"2026","journal-title":"Coord. Chem. Rev."},{"key":"2026101315090506500_cit27","doi-asserted-by":"publisher","first-page":"213464","DOI":"10.1016\/j.ccr.2020.213464","article-title":"Chalcogen\nbonding in materials chemistry","volume":"422","author":"Ho","year":"2020","journal-title":"Coord. 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Soc."},{"key":"2026101315090506500_cit31","doi-asserted-by":"publisher","first-page":"10608","DOI":"10.1021\/jacs.4c00262","article-title":"Harnessing\nmultistep chalcogen bonding activation in the \u03b1-stereoselective\nsynthesis of iminoglycosides","volume":"146","author":"Wang","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026101315090506500_cit32","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202517553","article-title":"Enhanced selectivity\nof chalcogen bonding over halogen\nbonding catalyzed C-glycosylation through differentiated intermediate\nactivation","volume":"65","author":"Guo","year":"2026","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101315090506500_cit33","doi-asserted-by":"publisher","first-page":"4383","DOI":"10.1021\/jm501853m","article-title":"A survey of the role of noncovalent sulfur interactions\nin drug design","volume":"58","author":"Beno","year":"2015","journal-title":"J. Med. Chem."},{"key":"2026101315090506500_cit34","doi-asserted-by":"publisher","first-page":"373","DOI":"10.1038\/s41557-025-01742-x","article-title":"Amphoteric chalcogen-bonding and\nhalogen-bonding rotaxanes\nfor anion or cation recognition","volume":"17","author":"Tse","year":"2025","journal-title":"Nat. Chem."},{"key":"2026101315090506500_cit35","doi-asserted-by":"publisher","first-page":"1622","DOI":"10.1021\/acschembio.1c00441","article-title":"Chalcogen\nbonds involving selenium\nin protein structures","volume":"16","author":"Carugo","year":"2021","journal-title":"ACS Chem. Biol."},{"key":"2026101315090506500_cit36","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.202100498","article-title":"Se\u00b7\u00b7\u00b7O\/S\nand S\u00b7\u00b7\u00b7O Chalcogen Bonds in Small Molecules and Proteins:\nA Combined CSD and PDB Study","volume":"23","author":"Biswal","year":"2022","journal-title":"ChemBioChem"},{"key":"2026101315090506500_cit37","doi-asserted-by":"publisher","first-page":"9576","DOI":"10.1080\/07391102.2022.2143427","article-title":"Chalcogen\nbonds formed by protein sulfur atoms in proteins. A survey of high-resolution\nstructures deposited in the protein data bank","volume":"41","author":"Carugo","year":"2023","journal-title":"J. Biomol. Struct. Dyn."},{"key":"2026101315090506500_cit38","doi-asserted-by":"publisher","first-page":"13035","DOI":"10.3390\/ijms241713035","article-title":"On the importance of halogen and\nchalcogen bonds in\nthe solid state of nucleic acids: A combined crystallographic and\ntheoretical perspective","volume":"24","author":"Pin\u0303a","year":"2023","journal-title":"Int. J. Mol. Sci."},{"key":"2026101315090506500_cit39","doi-asserted-by":"crossref","DOI":"10.1093\/acprof:oso\/9780199558964.001.0001","volume-title":"The Nature\nof the Hydrogen Bond: Outline\nof a Comprehensive Hydrogen Bond Theory","author":"Gilli","year":"2009"},{"key":"2026101315090506500_cit40","doi-asserted-by":"publisher","first-page":"21236","DOI":"10.1002\/anie.202010309","article-title":"The nature\nof strong chalcogen bonds involving chalcogen-containing\nheterocycles","volume":"59","author":"Haberhauer","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101315090506500_cit41","doi-asserted-by":"publisher","first-page":"1880","DOI":"10.1002\/anie.201809432","article-title":"Chalcogen\nbonding: An overview","volume":"58","author":"Vogel","year":"2019","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101315090506500_cit42","doi-asserted-by":"publisher","first-page":"557","DOI":"10.1002\/jcc.25099","article-title":"Characterization of chalcogen bonding interactions\nvia an in-depth conceptual quantum chemical analysis","volume":"39","author":"De Vleeschouwer","year":"2018","journal-title":"J. Comput. Chem."},{"key":"2026101315090506500_cit43","doi-asserted-by":"publisher","first-page":"3183","DOI":"10.1021\/jp501449v","article-title":"Effects of charge and substituent on the S\u00b7\u00b7\u00b7N\nchalcogen bond","volume":"118","author":"Adhikari","year":"2014","journal-title":"J. Phys. Chem. A"},{"key":"2026101315090506500_cit44","doi-asserted-by":"publisher","first-page":"10849","DOI":"10.1021\/jp509212t","article-title":"Chalcogen bonding between\ntetravalent SF4 and amines","volume":"118","author":"Nziko","year":"2014","journal-title":"J. Phys.\nChem. A"},{"key":"2026101315090506500_cit45","doi-asserted-by":"publisher","first-page":"2010","DOI":"10.1021\/acs.chemrev.7b00449","article-title":"From noncovalent\nchalcogen\u2013chalcogen interactions to supramolecular aggregates:\nExperiments and calculations","volume":"118","author":"Gleiter","year":"2018","journal-title":"Chem. Rev."},{"key":"2026101315090506500_cit46","doi-asserted-by":"publisher","first-page":"4188","DOI":"10.3390\/ijms23084188","article-title":"Metal coordination\nenhances chalcogen bonds: CSD survey\nand theoretical calculations","volume":"23","author":"Frontera","year":"2022","journal-title":"Int. J. Mol. Sci."},{"key":"2026101315090506500_cit47","doi-asserted-by":"publisher","first-page":"7766","DOI":"10.1039\/D5CE00869G","article-title":"Effect of a single\nchalcogen atom\nvariation on the chalcogen bond parameters: CSD analysis and theoretical\ncalculations","volume":"27","author":"Aliyeva","year":"2025","journal-title":"CrystEngComm"},{"key":"2026101315090506500_cit48","doi-asserted-by":"publisher","first-page":"3282","DOI":"10.1080\/00268976.2015.1017543","article-title":"Substituent\neffects in cooperativity of chalcogen bonds","volume":"113","author":"Esrafili","year":"2015","journal-title":"Mol. Phys."},{"key":"2026101315090506500_cit49","doi-asserted-by":"publisher","first-page":"44448","DOI":"10.1021\/acsomega.4c05963","article-title":"On the versatility\nof the sp-, sp2-, and sp3-hybridized chalcogen-bearing\nmolecules to engage in type I chalcogen\u00b7\u00b7\u00b7chalcogen\ninteractions: A quantum mechanical investigation of like\u00b7\u00b7\u00b7like\nand unlike complexes","volume":"9","author":"Ibrahim","year":"2024","journal-title":"ACS Omega"},{"key":"2026101315090506500_cit50","doi-asserted-by":"publisher","first-page":"3518","DOI":"10.1021\/acs.jpca.5b00783","article-title":"Se\u00b7\u00b7\u00b7N\nchalcogen bond and Se\u00b7\u00b7\u00b7X\nhalogen bond involving F2C=Se: Influence of hybridization,\nsubstitution, and cooperativity","volume":"119","author":"Guo","year":"2015","journal-title":"J. Phys. 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