{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T15:34:52Z","timestamp":1790696092724,"version":"4.1.0"},"reference-count":83,"publisher":"American Chemical Society (ACS)","issue":"24","license":[{"start":{"date-parts":[[2015,2,3]],"date-time":"2015-02-03T00:00:00Z","timestamp":1422921600000},"content-version":"vor","delay-in-days":365,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2014,6,19]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The charge distribution of halogen atoms on organochlorine compounds can be highly anisotropic and even display a so-called \u03c3-hole, which leads to strong halogen bonds with electron donors. In this paper, we have systematically investigated a series of chloromethanes with one to four chloro substituents using a polarizable multipole-based molecular mechanics model. The atomic multipoles accurately reproduced the ab initio electrostatic potential around chloromethanes, including CCl4, which has a prominent \u03c3-hole on the Cl atom. The van der Waals parameters for Cl were fitted to the experimental density and heat of vaporization. The calculated hydration free energy, solvent reaction fields, and interaction energies of several homo- and heterodimer of chloromethanes are in good agreement with experimental and ab initio data. This study suggests that sophisticated electrostatic models, such as polarizable atomic multipoles, are needed for accurate description of electrostatics in organochlorine compounds and halogen bonds, although further improvement is necessary for better transferability.<\/jats:p>","DOI":"10.1021\/jp411671a","type":"journal-article","created":{"date-parts":[[2014,2,3]],"date-time":"2014-02-03T03:08:06Z","timestamp":1391396886000},"page":"6456-6465","source":"Crossref","is-referenced-by-count":80,"title":["Modeling\nOrganochlorine Compounds and the \u03c3-Hole\nEffect Using a Polarizable Multipole Force Field"],"prefix":"10.1021","volume":"118","author":[{"given":"Xiaojiao","family":"Mu","sequence":"first","affiliation":[{"name":"The University of Texas at Austin , , ,","place":["Texas, United States, 78712"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiantao","family":"Wang","sequence":"additional","affiliation":[{"name":"The University of Texas at Austin , , ,","place":["Texas, United States, 78712"]},{"name":"The University of Texas at Austin , , ,","place":["Texas, United States, 78712"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lee-Ping","family":"Wang","sequence":"additional","affiliation":[{"name":"Stanford University , , , ,","place":["Stanford, California, United States, 94305"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen D.","family":"Fried","sequence":"additional","affiliation":[{"name":"Stanford University , , , ,","place":["Stanford, California, United States, 94305"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean-Philip","family":"Piquemal","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie The\u0301orique, Sorbonne Universite\u0301s, UPMC Paris 06, UMR 7616 , case courrier 137, 4 place Jussieu , , ,","place":["Paris, France, F-75005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kevin N.","family":"Dalby","sequence":"additional","affiliation":[{"name":"The University of Texas at Austin , , ,","place":["Texas, United States, 78712"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pengyu","family":"Ren","sequence":"additional","affiliation":[{"name":"The University of Texas at Austin , , ,","place":["Texas, United States, 78712"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2014,2,3]]},"reference":[{"issue":"15","key":"2026090115030225300_cit1","doi-asserted-by":"crossref","first-page":"6810","DOI":"10.1021\/ja301056a","article-title":"Halogen-Enriched\nFragment Libraries as Leads for Drug Rescue of Mutant P53","volume":"134","author":"Wilcken","year":"2012","journal-title":"J. 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R.\n          \n          Macromolecular Halogen\nBonds; Ph.D. Dissertation, Oregon State University, 2007."},{"issue":"23","key":"2026090115030225300_cit6","doi-asserted-by":"crossref","first-page":"2032","DOI":"10.1002\/jcc.23362","article-title":"A Polarizable Ellipsoidal\nForce Field for Halogen Bonds","volume":"34","author":"Du","year":"2013","journal-title":"J. Comput. Chem."},{"issue":"12","key":"2026090115030225300_cit7","doi-asserted-by":"crossref","first-page":"3309","DOI":"10.1007\/s00894-011-1015-6","article-title":"Halogen Bond\nTunability I: The Effects of Aromatic Fluorine Substitution on the\nStrengths of Halogen-Bonding Interactions Involving Chlorine, Bromine,\nand Iodine","volume":"17","author":"Riley","year":"2011","journal-title":"J. Mol. Model."},{"issue":"11","key":"2026090115030225300_cit8","doi-asserted-by":"crossref","first-page":"4651","DOI":"10.1007\/s00894-012-1428-x","article-title":"Halogen Bond\nTunability Ii: The Varying Roles of Electrostatic and Dispersion Contributions\nto Attraction in Halogen Bonds","volume":"19","author":"Riley","year":"2013","journal-title":"J. Mol. Model."},{"issue":"2","key":"2026090115030225300_cit9","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1007\/s00894-006-0130-2","article-title":"Halogen Bonding: The\n\u03a3-Hole","volume":"13","author":"Clark","year":"2007","journal-title":"J. Mol. Model."},{"issue":"15","key":"2026090115030225300_cit10","doi-asserted-by":"crossref","first-page":"3046","DOI":"10.1002\/qua.21419","article-title":"\u03a3-Hole\nBonding and Hydrogen\nBonding: Competitive Interactions","volume":"107","author":"Politzer","year":"2007","journal-title":"Int. J. 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