{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,12]],"date-time":"2026-07-12T00:11:19Z","timestamp":1783815079359,"version":"3.55.0"},"reference-count":69,"publisher":"American Chemical Society (ACS)","issue":"10","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Chem. Inf. Model."],"published-print":{"date-parts":[[2009,10,26]]},"DOI":"10.1021\/ci9002393","type":"journal-article","created":{"date-parts":[[2009,9,29]],"date-time":"2009-09-29T20:10:46Z","timestamp":1254255046000},"page":"2344-2355","source":"Crossref","is-referenced-by-count":255,"title":["Fluorine Bonding \u2014 How Does It Work In Protein\u2212Ligand Interactions?"],"prefix":"10.1021","volume":"49","author":[{"given":"Peng","family":"Zhou","sequence":"first","affiliation":[{"name":"Department of Chemistry, Zhejiang University, Hangzhou 310027, China, Key Laboratory for Molecular Design and Nutrition Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China, College of Bioengineering, Chongqing University, Chongqing 400044, China, and Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianwei","family":"Zou","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Zhejiang University, Hangzhou 310027, China, Key Laboratory for Molecular Design and Nutrition Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China, College of Bioengineering, Chongqing University, Chongqing 400044, China, and Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Feifei","family":"Tian","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Zhejiang University, Hangzhou 310027, China, Key Laboratory for Molecular Design and Nutrition Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China, College of Bioengineering, Chongqing University, Chongqing 400044, China, and Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhicai","family":"Shang","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Zhejiang University, Hangzhou 310027, China, Key Laboratory for Molecular Design and Nutrition Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China, College of Bioengineering, Chongqing University, Chongqing 400044, China, and Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2009,9,29]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"386","DOI":"10.1021\/ar0400995","volume":"38","author":"Metrangolo P.","year":"2005","journal-title":"Acc. Chem. Res."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1007\/s00894-006-0154-7","volume":"13","author":"Politzer P.","year":"2007","journal-title":"J. Mol. Model."},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1002\/chem.19970030115","volume":"3","author":"Dunitz J. D.","year":"1997","journal-title":"Chem.\u2014Eur. J."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1016\/0022-2860(96)09242-3","volume":"382","author":"Alkortaa I.","year":"1996","journal-title":"J. Mol. Struct."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"395","DOI":"10.1039\/B311000A","volume":"5","author":"Ahuja R.","year":"2003","journal-title":"CrystEngComm"},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"8952","DOI":"10.1002\/chem.200600523","volume":"12","author":"Awwadi F. F.","year":"2006","journal-title":"Chem.\u2014Eur. J."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"6744","DOI":"10.1021\/jp047646o","volume":"108","author":"Kawahara S.","year":"2004","journal-title":"J. Phys. Chem. A"},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"17752","DOI":"10.1021\/jp052411d","volume":"109","author":"Riley K. E.","year":"2005","journal-title":"J. Phys. Chem. B"},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.molstruc.2007.11.040","volume":"888","author":"Chopra D.","year":"2008","journal-title":"J. Mol. Struct."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1039\/b202557d","volume":"1","author":"Vishnumurthy K.","year":"2002","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"4483","DOI":"10.1002\/ejoc.200500205","volume":"21","author":"J\u00e4ckel C.","year":"2005","journal-title":"Eur. J. Org. Chem."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"2705","DOI":"10.1039\/DT9940002705","author":"Borisenko K. B.","year":"1994","journal-title":"J. Chem. Soc., Dalton Trans."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"1902","DOI":"10.1021\/ja016348r","volume":"124","author":"Iwaoka M.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"3669","DOI":"10.1021\/jp045044z","volume":"109","author":"Matta C. F.","year":"2005","journal-title":"J. Phys. Chem. A"},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1021\/cg0300228","volume":"4","author":"Lee S.","year":"2004","journal-title":"Cryst. Growth Des."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"2507","DOI":"10.1002\/anie.200351268","volume":"42","author":"Olsen J. A.","year":"2003","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1002\/cbic.200300752","volume":"5","author":"Plenio H.","year":"2004","journal-title":"ChemBioChem"},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"710","DOI":"10.1016\/j.ccr.2005.04.031","volume":"250","author":"Kov\u00e1cs A.","year":"2006","journal-title":"Coord. Chem. Rev."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"1169","DOI":"10.1002\/cphc.200400324","volume":"6","author":"Bettinger H. F.","year":"2005","journal-title":"ChemPhysChem"},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"5664","DOI":"10.1021\/ja012116g","volume":"124","author":"Parsch J.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"5114","DOI":"10.1021\/jm0498349","volume":"47","author":"Carosati E.","year":"2004","journal-title":"J. Med. Chem."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1007\/s00894-007-0176-9","volume":"13","author":"Politzer P.","year":"2007","journal-title":"J. Mol. Model."},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1016\/j.cplett.2007.09.087","volume":"449","author":"Lu Y.","year":"2007","journal-title":"Chem. Phys. Lett."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1007\/s00894-006-0130-2","volume":"13","author":"Clark T.","year":"2007","journal-title":"J. Mol. Model."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"1033","DOI":"10.1007\/s00894-007-0225-4","volume":"13","author":"Murray J. S.","year":"2007","journal-title":"J. Mol. Model."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"659","DOI":"10.1007\/s00894-008-0280-5","volume":"14","author":"Politzer P.","year":"2008","journal-title":"J. Mol. Model."},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"699","DOI":"10.1007\/s00894-008-0307-y","volume":"14","author":"Murray J. S.","year":"2008","journal-title":"J. Mol. Model."},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"723","DOI":"10.1007\/s00894-008-0386-9","volume":"15","author":"Murray J. S.","year":"2009","journal-title":"J. Mol. Model."},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"637","DOI":"10.1002\/cbic.200301023","volume":"5","author":"B\u00f6hm H.","year":"2004","journal-title":"ChemBioChem"},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"676","DOI":"10.1002\/cbic.200400017","volume":"5","author":"Gerebtzoff G.","year":"2004","journal-title":"ChemBioChem"},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"1881","DOI":"10.1126\/science.1131943","volume":"317","author":"M\u00fcller K.","year":"2007","journal-title":"Science"},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"570","DOI":"10.1002\/cbic.200300833","volume":"5","author":"Jeschke P.","year":"2004","journal-title":"ChemBioChem"},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"1788","DOI":"10.1002\/anie.200462213","volume":"44","author":"Paulini R.","year":"2005","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"9620","DOI":"10.1021\/ja011034p","volume":"123","author":"Kim C.","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1093\/nar\/28.1.235","volume":"28","author":"Berman H. M.","year":"2000","journal-title":"Nucleic Acids Res."},{"key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"D238","DOI":"10.1093\/nar\/gki059","volume":"33","author":"Shin J.","year":"2005","journal-title":"Nucleic Acids Res."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"16789","DOI":"10.1073\/pnas.0407607101","volume":"101","author":"Auffinger P.","year":"2004","journal-title":"Proc. Natl. Acad. Sci., U.S.A."},{"key":"ref38\/cit38","author":"Krivov G. G.","year":"2009","journal-title":"Proteins"},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"1735","DOI":"10.1006\/jmbi.1998.2401","volume":"285","author":"Word J. M.","year":"1999","journal-title":"J. Mol. Biol."},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1002\/prot.22327","volume":"76","author":"Zhou P.","year":"2009","journal-title":"Proteins"},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1021\/j100785a001","volume":"68","author":"Bondi A.","year":"1964","journal-title":"J. Phys. Chem."},{"key":"ref42\/cit42","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1103\/PhysRev.46.618","volume":"46","author":"M\u00f8ller C.","year":"1934","journal-title":"Phys. Rev."},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"1007","DOI":"10.1063\/1.456153","volume":"90","author":"Dunning T. H., Jr.","year":"1989","journal-title":"J. Chem. Phys."},{"key":"ref44\/cit44","doi-asserted-by":"crossref","first-page":"2015","DOI":"10.1002\/qua.21353","volume":"107","author":"Sahu P. K.","year":"2007","journal-title":"Int. J. Quantum Chem."},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1007\/BF01171765","volume":"13","author":"Chesnut D. B.","year":"1969","journal-title":"Theor. Chim. Acta."},{"key":"ref46\/cit46","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1080\/00268977000101561","volume":"19","author":"Boys S. F.","year":"1970","journal-title":"Mol. Phys."},{"key":"ref47\/cit47","doi-asserted-by":"crossref","first-page":"19357","DOI":"10.1021\/jp962071j","volume":"100","author":"Svensson M.","year":"1996","journal-title":"J. Phys. Chem."},{"key":"ref48\/cit48","doi-asserted-by":"crossref","first-page":"664","DOI":"10.1063\/1.475428","volume":"108","author":"Adamo C.","year":"1998","journal-title":"J. Chem. Phys."},{"key":"ref49\/cit49","doi-asserted-by":"crossref","first-page":"5179","DOI":"10.1021\/ja00124a002","volume":"117","author":"Cornell W. D.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref50\/cit50","doi-asserted-by":"crossref","first-page":"2854","DOI":"10.1021\/jm9000133","volume":"52","author":"Lu Y.","year":"2009","journal-title":"J. Med. Chem."},{"key":"ref51\/cit51","doi-asserted-by":"crossref","first-page":"926","DOI":"10.1063\/1.445869","volume":"79","author":"Jorgensen W. L.","year":"1983","journal-title":"J. Chem. Phys."},{"key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"9620","DOI":"10.1021\/ja00074a030","volume":"115","author":"Comell W. D.","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ref53\/cit53","doi-asserted-by":"crossref","first-page":"1157","DOI":"10.1002\/jcc.20035","volume":"25","author":"Wang J.","year":"2004","journal-title":"J. Comput. Chem."},{"key":"ref54\/cit54","doi-asserted-by":"crossref","first-page":"886","DOI":"10.1021\/ci8004034","volume":"49","author":"Alzate-Morales J. H.","year":"2009","journal-title":"J. Chem. Inf. Model."},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"666","DOI":"10.1002\/cbic.200300907","volume":"5","author":"Olsen J. A.","year":"2004","journal-title":"ChemBioChem"},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"6946","DOI":"10.1073\/pnas.0307578101","volume":"101","author":"Morozov A. V.","year":"2004","journal-title":"Proc. Natl. Acad. Sci., U.S.A."},{"key":"ref57\/cit57","doi-asserted-by":"crossref","first-page":"1473","DOI":"10.2174\/156802606777951127","volume":"6","author":"DiMagno S.","year":"2006","journal-title":"Curr. Top. Med. Chem."},{"key":"ref58\/cit58","doi-asserted-by":"crossref","first-page":"2993","DOI":"10.1021\/jp952860l","volume":"100","author":"Feyereisen M. W.","year":"1996","journal-title":"J. Phys. Chem."},{"key":"ref59\/cit59","doi-asserted-by":"crossref","first-page":"5761","DOI":"10.1021\/ja00356a010","volume":"105","author":"Taylor R.","year":"1983","journal-title":"J. Am. Chem. Soc."},{"key":"ref60\/cit60","doi-asserted-by":"crossref","first-page":"412","DOI":"10.1021\/jp052809+","volume":"110","author":"Yerushalmi R.","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref61\/cit61","doi-asserted-by":"crossref","first-page":"1739","DOI":"10.1002\/anie.199517391","volume":"34","author":"Obst U.","year":"1995","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref62\/cit62","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1016\/S1074-5521(97)90072-7","volume":"4","author":"Obst U.","year":"1997","journal-title":"Chem. Biol."},{"key":"ref63\/cit63","doi-asserted-by":"crossref","first-page":"5056","DOI":"10.1002\/anie.200460781","volume":"43","author":"Hof F.","year":"2004","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref64\/cit64","doi-asserted-by":"crossref","first-page":"7211","DOI":"10.1021\/ja00544a007","volume":"102","author":"Foster J. P.","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"ref65\/cit65","doi-asserted-by":"crossref","first-page":"725","DOI":"10.1002\/jcc.21094","volume":"30","author":"Lu Y.","year":"2009","journal-title":"J. Comput. Chem."},{"key":"ref66\/cit66","doi-asserted-by":"crossref","first-page":"12956","DOI":"10.1073\/pnas.95.22.12956","volume":"95","author":"Peterson S. A.","year":"1998","journal-title":"Proc. Natl. Acad. Sci., U.S.A."},{"key":"ref67\/cit67","doi-asserted-by":"crossref","first-page":"12125","DOI":"10.1021\/ja002627n","volume":"122","author":"Kim C.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref68\/cit68","doi-asserted-by":"crossref","first-page":"1737","DOI":"10.1021\/ja043475p","volume":"127","author":"S\u00f6rme P.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref69\/cit69","doi-asserted-by":"crossref","first-page":"D674","DOI":"10.1093\/nar\/gkm911","volume":"36","author":"Benson M. L.","year":"2008","journal-title":"Nucleic Acids Res."}],"container-title":["Journal of Chemical Information and Modeling"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ci9002393","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,5]],"date-time":"2023-03-05T09:37:10Z","timestamp":1678009030000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ci9002393"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,9,29]]},"references-count":69,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2009,10,26]]}},"alternative-id":["10.1021\/ci9002393"],"URL":"https:\/\/doi.org\/10.1021\/ci9002393","relation":{},"ISSN":["1549-9596","1549-960X"],"issn-type":[{"value":"1549-9596","type":"print"},{"value":"1549-960X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,9,29]]}}}