{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,5]],"date-time":"2026-06-05T10:42:04Z","timestamp":1780656124580,"version":"3.54.1"},"reference-count":31,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2025,12,3]],"date-time":"2025-12-03T00:00:00Z","timestamp":1764720000000},"content-version":"vor","delay-in-days":2,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2025,12]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    The resolution behavior of chiral compounds containing two carboxyl groups remains an interesting subject due to their potential for forming complex stereospecific interactions. In this study, a representative for this group of compounds,\n                    <jats:italic>trans<\/jats:italic>\n                    \u20101,2\u2010cyclohexanedicarboxylic acid (CHDA) was enantiomerically separated using optically active (1\n                    <jats:italic>S<\/jats:italic>\n                    ,2\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010(+)\u20101\u2010(\n                    <jats:italic>p<\/jats:italic>\n                    \u2010nitrophenyl)\u20102\u2010amino\u20101,3\u2010propanediol ((\n                    <jats:italic>SS<\/jats:italic>\n                    )\u2010ANP) as a resolving agent in ethanol solvent. Remarkably, regardless of the initial molar ratio of (\n                    <jats:italic>SS<\/jats:italic>\n                    )\u2010ANP to CHDA (ranging from 1:3 to 3:1), only a cocrystal, di\u2010(\n                    <jats:italic>SS<\/jats:italic>\n                    )\u2010ANP\u00b7CHDA\u00b7ethanol was obtained. When the molar ratio was adjusted to 1:2, a pair of diastereomeric salts was formed, and (\n                    <jats:italic>RR<\/jats:italic>\n                    )\u2010CHDA freed from the less soluble diastereomeric salt exhibited an enantiomeric excess (e.e.) exceeding 85%. Upon two cycles of recrystallization of the less soluble salts, the optical purity of the freed (\n                    <jats:italic>RR<\/jats:italic>\n                    )\u2010CHDA reached 96.5\u2009e.e.%. To elucidate the resolution mechanism, single crystals of both the less soluble salt 2(\n                    <jats:italic>SS<\/jats:italic>\n                    )\u2010ANP\u00b7(\n                    <jats:italic>RR<\/jats:italic>\n                    )\u2010CHDA\u00b7ethanol and the more soluble salt 2(\n                    <jats:italic>RR<\/jats:italic>\n                    )\u2010ANP\u00b7(\n                    <jats:italic>RR<\/jats:italic>\n                    )\u2010CHDA\u00b7ethanol were grown and structurally analyzed. The crystallographic data revealed that the hydrogen bonding in the less soluble salt was stronger than that in the more soluble salt, enhancing the stability of the less soluble salt, 2(\n                    <jats:italic>SS<\/jats:italic>\n                    )\u2010ANP\u00b7(\n                    <jats:italic>RR<\/jats:italic>\n                    )\u2010CHDA\u00b7ethanol.\n                  <\/jats:p>","DOI":"10.1002\/chir.70067","type":"journal-article","created":{"date-parts":[[2025,12,4]],"date-time":"2025-12-04T04:20:19Z","timestamp":1764822019000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Resolution Characteristics of Optically Active (1\n                    <scp>\n                      <i>S<\/i>\n                    <\/scp>\n                    ,2\n                    <scp>\n                      <i>S<\/i>\n                    <\/scp>\n                    )\u2010(+)\u20101\u2010(\n                    <scp>\n                      <i>p<\/i>\n                    <\/scp>\n                    \u2010Nitrophenyl)\u20102\u2010Amino\u20101,3\u2010Propanediol for\n                    <scp>\n                      <i>trans<\/i>\n                    <\/scp>\n                    \u20101,2\u2010Cyclohexanedicarboxylic Acid"],"prefix":"10.1002","volume":"37","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-2631-5201","authenticated-orcid":false,"given":"Haibing","family":"Jin","sequence":"first","affiliation":[{"name":"School of Chemical Engineering East China University of Science and Technology  Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1316-4090","authenticated-orcid":false,"given":"Yangfeng","family":"Peng","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering East China University of Science and Technology  Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tianzhong","family":"Tong","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering East China University of Science and Technology  Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hongliang","family":"Zhao","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering East China University of Science and Technology  Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yani","family":"Dai","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering East China University of Science and Technology  Shanghai China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Quan","family":"He","sequence":"additional","affiliation":[{"name":"Department of Engineering, Faculty of Agriculture Dalhousie University  Truro Nova Scotia Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,12,3]]},"reference":[{"issue":"21","key":"e_1_2_7_2_1","first-page":"635","article-title":"Research Progress in Chiral Compounds","volume":"9","author":"Yu P.","year":"2002","journal-title":"Chemical Industry and Engineering Progress"},{"issue":"53","key":"e_1_2_7_3_1","first-page":"37","article-title":"Research Progress of Resolution of Chiral Drugs and Their Synthetic Intermediates","volume":"1","author":"Liu W. 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