{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T11:48:19Z","timestamp":1777463299785,"version":"3.51.4"},"reference-count":87,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2012,4,18]],"date-time":"2012-04-18T00:00:00Z","timestamp":1334707200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2012,5,29]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>An investigation into the predictability of molecular adduct formation is presented by using the approach of hydrogen bond propensity. Along with the predictions, crystallisation reactions (<jats:bold>1a<\/jats:bold>\u2013<jats:bold>1j<\/jats:bold>) were carried out between the anti\u2010malarial drug pyrimethamine (<jats:bold>1<\/jats:bold>) and the acids oxalic (<jats:bold>a<\/jats:bold>), malonic (<jats:bold>b<\/jats:bold>), acetylenedicarboxylic (<jats:bold>c<\/jats:bold>), adipic (<jats:bold>d<\/jats:bold>), pimelic (<jats:bold>e<\/jats:bold>), suberic (<jats:bold>f<\/jats:bold>), azelaic acids (<jats:bold>g<\/jats:bold>), as well as hexachlorobenzene (<jats:bold>h<\/jats:bold>), 1,4\u2010diiodobenzene (<jats:bold>i<\/jats:bold>), and 1,4\u2010diiodotetrafluorobenzene (<jats:bold>j<\/jats:bold>); seven (<jats:bold>1a<\/jats:bold> to <jats:bold>1g<\/jats:bold>) of these successfully formed salts. Five of these seven salts were found to be either hydrated or solvated. Hydrogen bond propensity calculations predict that hydrogen bonds between <jats:bold>1<\/jats:bold> and acids <jats:bold>a<\/jats:bold>\u2013<jats:bold>g<\/jats:bold> are more likely to form rather than the H bonds involved in self\u2010association, providing a rationale for the observation of the seven new salts. In contrast, propensity of hydrogen bonds between <jats:bold>1<\/jats:bold> and <jats:bold>h<\/jats:bold>\u2013<jats:bold>j<\/jats:bold> is much smaller as compared to other bonds predicted for self\u2010association\/solvate formation, in agreement with the observed unsuccessful reactions.<\/jats:p>","DOI":"10.1002\/chem.201103129","type":"journal-article","created":{"date-parts":[[2012,4,18]],"date-time":"2012-04-18T03:19:12Z","timestamp":1334719152000},"page":"6835-6846","source":"Crossref","is-referenced-by-count":80,"title":["Quantifying Homo\u2010 and Heteromolecular Hydrogen Bonds as a Guide for Adduct Formation"],"prefix":"10.1002","volume":"18","author":[{"given":"Amit","family":"Delori","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Peter T. A.","family":"Galek","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elna","family":"Pidcock","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"William","family":"Jones","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,4,18]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg034035x"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/b501304f"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/jps.20927"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/mp200043u"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.2042-7158.2010.01133.x"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201002588"},{"key":"e_1_2_6_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201002588"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.859"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja035776p"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/b416137h"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg8005025"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg050125l"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg901232h"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg9001187"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg800621q"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja907674c"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ce00787k"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg200334m"},{"key":"e_1_2_6_20_2","unstructured":"\u00a0"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg901010v"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejpb.2006.12.016"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11095-006-9032-3"},{"key":"e_1_2_6_24_2","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/b208574g"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ce00253d"},{"key":"e_1_2_6_27_2","unstructured":"\u00a0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg0496540"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijpharm.2006.04.018"},{"key":"e_1_2_6_30_2","unstructured":"\u00a0"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200900533"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg060398w"},{"key":"e_1_2_6_33_2","unstructured":"\u00a0"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ce00428f"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502434"},{"key":"e_1_2_6_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502434"},{"key":"e_1_2_6_36_2","unstructured":"\u00a0"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0sc00555j"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200301739"},{"key":"e_1_2_6_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200301739"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/b707518a"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg800371j"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg800685z"},{"key":"e_1_2_6_42_2","unstructured":"\u00a0"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg800861m"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg801122m"},{"key":"e_1_2_6_45_2","unstructured":"\u00a0"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951072105"},{"key":"e_1_2_6_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199523111"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/jps.22117"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1039\/b608926g"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg801145c"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg800565a"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg8007359"},{"key":"e_1_2_6_52_2","unstructured":"\u00a0"},{"key":"e_1_2_6_53_2","first-page":"11","volume":"8","author":"Chrisholm J.","year":"2006","journal-title":"CrystEngComm"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/b926745j"},{"key":"e_1_2_6_55_2","unstructured":"\u00a0"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108768107030996"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1039\/b910882c"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1039\/b927246a"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108768110003988"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CE06362J"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1524\/zkri.220.4.333.61617"},{"key":"e_1_2_6_62_2","unstructured":"Propensity calculations were carried out with a newer version of mercury software (mercury\u20052.4.1\u2009cfc) which is under development by CCDC. For these calculations conquest version\u20051.13 was used as database."},{"key":"e_1_2_6_63_2","unstructured":"The pKavalue of pyrimethamine was calculated by using sparc online calculatorhttp:\/\/sparc.chem.uga.edu\/sparc\/. The pKavalues of acids were obtained from: pKaData Compiled by R.\u2005Williams."},{"key":"e_1_2_6_64_2","unstructured":"\u00a0"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/b509162d"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800649"},{"key":"e_1_2_6_67_2","unstructured":"\u00a0"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg100514g"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ce00052c"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/mp060126o"},{"key":"e_1_2_6_71_2","unstructured":"\u00a0"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1039\/B512626F"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg030015j"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg020027p"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1107\/S1600536802011133"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1107\/S1600536807044364"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1039\/b207369m"},{"key":"e_1_2_6_78_2","unstructured":"\u00a0"},{"key":"e_1_2_6_79_2","unstructured":"Siemens SMART System Siemens Analytical X\u2010ray Instruments Inc. Madison WI (USA) 1995;"},{"key":"e_1_2_6_80_2","unstructured":"G.\u2005M. Sheldrick Siemens Area Detector Absorption Correction Program (SADABS) University of G\u00f6ttingen G\u00f6ttingen Germany 1994;"},{"key":"e_1_2_6_81_2","unstructured":"G.\u2005M. Sheldrick SHELXTL\u2010PLUS program for crystal structure solution and refinement University of G\u00f6ttingen G\u00f6ttingen Germany."},{"key":"e_1_2_6_82_2","unstructured":"A.\u2005L. Spek PLATON molecular geometry program University of Utrecht The Netherlands 1995."},{"key":"e_1_2_6_83_2","unstructured":"Diamond\u2013Crystal and Molecular Structure Visualization Version\u20053.1f Crystal Impact Brandenburg & Putz Bonn 2008."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201103129","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201103129","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T21:39:24Z","timestamp":1760305164000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201103129"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,4,18]]},"references-count":87,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2012,5,29]]}},"alternative-id":["10.1002\/chem.201103129"],"URL":"https:\/\/doi.org\/10.1002\/chem.201103129","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,4,18]]}}}