{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,26]],"date-time":"2026-04-26T09:22:25Z","timestamp":1777195345572,"version":"3.51.4"},"reference-count":61,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2019,9,13]],"date-time":"2019-09-13T00:00:00Z","timestamp":1568332800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100002660","name":"Islamic Azad University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100002660","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J Comput Chem"],"published-print":{"date-parts":[[2019,12,15]]},"abstract":"<jats:p>This work studies the underlying nature of H\u2010bonds (HBs) of different types and strengths and tries to predict binding energies (BEs) based on the properties derived from wave function analysis. A total of 42 HB complexes constructed from 28 neutral and 14 charged monomers were considered. This set was designed to sample a wide range of HB strengths to obtain a complete view about HBs. BEs were derived with the accurate coupled cluster singles and doubles with perturbative triples correction (CCSD(T))(T) method and the physical components of the BE were investigated by symmetry\u2010adapted perturbation theory (SAPT). Quantum theory of atoms\u2010in\u2010molecules (QTAIM) descriptors and other HB indices were calculated based on high\u2010quality density functional theory wave functions. We propose a new and rigorous classification of H\u2010bonds (HBs) based on the SAPT decomposition. Neutral complexes are either classified as \u201cvery weak\u201d HBs with a BE \u2265 \u22122.5\u2009kcal\/mol that are mainly dominated by both dispersion and electrostatic interactions or as \u201cweak\u2010to\u2010medium\u201d HBs with a BE varying between \u22122.5 and\u2009\u221214.0\u2009kcal\/mol that are only dominated by electrostatic interactions. On the other hand, charged complexes are divided into \u201cmedium\u201d HBs with a BE in the range of \u221211.0 to \u221215.0\u2009kcal\/mol, which are mainly dominated by electrostatic interactions, or into \u201cstrong\u201d HBs whose BE is more negative than \u221215.0\u2009kcal\/mol, which are mainly dominated by electrostatic together with induction interactions. Among various explored correlations between BEs and wave function\u2010based HB descriptors, a fairly satisfactory correlation was found for the electron density at the bond critical point (BCP;<jats:styled-content><jats:italic>\u03c1<\/jats:italic><jats:sub>BCP<\/jats:sub><\/jats:styled-content>) of HBs. The fitted equation for neutral complexes is BE<jats:styled-content>\/kcal\/mol = \u2009\u2212\u2009223.08\u2009\u00d7\u2009<jats:italic>\u03c1<\/jats:italic><jats:sub>BCP<\/jats:sub>\/a. u.\u2009+\u20090.7423<\/jats:styled-content>with a mean absolute percentage error (MAPE) of 14.7%, while that for charged complexes is BE<jats:styled-content>\/kcal\/mol = \u2009\u2212\u2009332.34\u2009\u00d7\u2009<jats:italic>\u03c1<\/jats:italic><jats:sub>BCP<\/jats:sub>\/a. u.\u2009\u2212\u20091.0661<\/jats:styled-content>with a MAPE of 10.0%. In practice, these equations may be used for a quick estimation of HB BEs, for example, for intramolecular HBs or large HB networks in biomolecules. \u00a9 2019 Wiley Periodicals, Inc.<\/jats:p>","DOI":"10.1002\/jcc.26068","type":"journal-article","created":{"date-parts":[[2019,9,13]],"date-time":"2019-09-13T13:41:27Z","timestamp":1568382087000},"page":"2868-2881","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1444,"title":["Exploring Nature and Predicting Strength of Hydrogen Bonds: A Correlation Analysis Between Atoms\u2010in\u2010Molecules Descriptors, Binding Energies, and Energy Components of Symmetry\u2010Adapted Perturbation Theory"],"prefix":"10.1002","volume":"40","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8223-1264","authenticated-orcid":false,"given":"Saeedreza","family":"Emamian","sequence":"first","affiliation":[{"name":"Chemistry Department Shahrood Branch, Islamic Azad University Shahrood Iran"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1822-1229","authenticated-orcid":false,"given":"Tian","family":"Lu","sequence":"additional","affiliation":[{"name":"Beijing Kein Research Center for Natural Sciences Beijing 100022 People's Republic of China"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0560-1513","authenticated-orcid":false,"given":"Holger","family":"Kruse","sequence":"additional","affiliation":[{"name":"Institute of Biophysics of the Czech Academy of Sciences, Kr\u00e1lovopolsk\u00e1 135, 612 65 Brno Czech Republic"}]},{"given":"Hamidreza","family":"Emamian","sequence":"additional","affiliation":[{"name":"Materials Science &amp; Metallurgy Department, Technology &amp; Processing of New Materials Research Center, Neyshabur Branch Islamic Azad University Neyshabur Iran"}]}],"member":"311","published-online":{"date-parts":[[2019,9,13]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1074-5521(97)90069-7"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.physchem.48.1.511"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470141700.ch1"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0567740876003968"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527616091.ch11"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199013041"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.7b00598"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1351\/PAC-REC-10-01-02"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.8"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00526"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.84"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0009-2614(89)87395-6"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.8b00643"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.4867135"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00894-013-2034-2"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/qua.25443"},{"key":"e_1_2_7_18_1","doi-asserted-by":"crossref","DOI":"10.1093\/oso\/9780198551683.001.0001","volume-title":"Atoms in Molecules: A Quantum Theory","author":"Bader R. 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