{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T18:17:33Z","timestamp":1787509053057,"version":"build-2736575974"},"reference-count":39,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2009,7,30]],"date-time":"2009-07-30T00:00:00Z","timestamp":1248912000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2010,5,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Following the computation of a lattice energy landscape which predicted that there should be more stable, denser forms of (R)\u20101\u2010phenylethylammonium\u2010(S)\u20102\u2010phenylbutyrate, crystallizations from a range of solvents were performed to search for other polymorphs and investigate the possibility that the known\n                    <jats:italic>P<\/jats:italic>\n                    4\n                    <jats:sub>1<\/jats:sub>\n                    structure could be a hydrate. Extensive crystallization experiments from a wide range of solvents gave fine needles or microcrystalline samples. A redetermination of the\n                    <jats:italic>P<\/jats:italic>\n                    4\n                    <jats:sub>1<\/jats:sub>\n                    structure by powder X\u2010ray diffraction located all protons, and in conjunction with other experimental and computational evidence showed that the structure was anhydrous. Evidence for two additional forms was found as mixtures with form I. These include an orthorhombic form, possibly a\n                    <jats:italic>Z<\/jats:italic>\n                    \u2032 = 3 polymorph, and another as yet unidentified form obtained as a minor component from dichloromethane solution. However, both these forms appear to be metastable with respect to form I (\n                    <jats:italic>P<\/jats:italic>\n                    4\n                    <jats:sub>1<\/jats:sub>\n                    ), which is therefore probably the most thermodynamically stable form that can be crystallized from solution under ambient conditions. This determination of the solid state behavior of the less readily crystallized member of the diastereomeric salt system (R)\u20101\u2010phenylethylammonium\u2010(R\/S)\u20102\u2010phenylbutyrate provides a challenge to the theoretical modeling to explain its ideal resolution behavior. Chirality 2010. \u00a9 2009 Wiley\u2010Liss, Inc.\n                  <\/jats:p>","DOI":"10.1002\/chir.20761","type":"journal-article","created":{"date-parts":[[2009,7,30]],"date-time":"2009-07-30T09:20:29Z","timestamp":1248945629000},"page":"447-455","source":"Crossref","is-referenced-by-count":8,"title":["A computationally inspired investigation of the solid forms of (R)\u20101\u2010phenylethylammonium\u2010(S)\u20102\u2010phenylbutyrate"],"prefix":"10.1002","volume":"22","author":[{"given":"Constantinos D.","family":"Antoniadis","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emiliana","family":"D'Oria","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Panagiotis G.","family":"Karamertzanis","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Derek A.","family":"Tocher","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alastair J.","family":"Florence","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sarah L.","family":"Price","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alan G.","family":"Jones","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,7,30]]},"reference":[{"key":"e_1_2_1_2_2","volume-title":"CRC Handbook of optical resolutions via diastereomeric salt formation","author":"Kozma D","year":"2002"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/aic.690470102"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp068530q"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0567740881004147"},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/b719351c"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2006.06.038"},{"key":"e_1_2_1_8_2","doi-asserted-by":"publisher","DOI":"10.1107\/S1600536806052652"},{"key":"e_1_2_1_9_2","first-page":"202","article-title":"Structure solution and Rietveld refinement of form III of R\u20101\u2010phenylethylammonium R\u20102\u2010phenylbutyrate salt","volume":"63","author":"Fernades P","year":"2007","journal-title":"Acta Crystallogr E"},{"key":"e_1_2_1_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg0601756"},{"key":"e_1_2_1_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/b006604o"},{"key":"e_1_2_1_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ct600111s"},{"key":"e_1_2_1_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/b701299c"},{"key":"e_1_2_1_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/b708303n"},{"key":"e_1_2_1_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/jps.20647"},{"key":"e_1_2_1_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cg034035x"},{"key":"e_1_2_1_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/b713373a"},{"key":"e_1_2_1_18_2","first-page":"98","volume-title":"Structure determination from powder diffraction data","author":"Hill RJ","year":"2002"},{"key":"e_1_2_1_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/a606998c"},{"key":"e_1_2_1_20_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889891006441"},{"key":"e_1_2_1_21_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889806042117"},{"key":"e_1_2_1_22_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889869006558"},{"key":"e_1_2_1_23_2","volume-title":"Topas user manual","author":"Coelho AA","year":"2004"},{"key":"e_1_2_1_24_2","volume-title":"Gaussian 03","author":"Frisch MJ","year":"2003"},{"key":"e_1_2_1_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ct050190"},{"key":"e_1_2_1_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp960333b"},{"key":"e_1_2_1_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ct700045r"},{"key":"e_1_2_1_28_2","unstructured":"Department of Chemistry University College London.DMACRYS version 1.05 is a substantial revision of DMAREL. London UK;2008."},{"key":"e_1_2_1_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.540160511"},{"key":"e_1_2_1_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/b515612m"},{"key":"e_1_2_1_31_2","first-page":"446","article-title":"A new law of crystal morphology extending the Law of Bravais","volume":"22","author":"Donnay JDH","year":"1937","journal-title":"Am Mineral"},{"key":"e_1_2_1_32_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767300012174"},{"key":"e_1_2_1_33_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108768102003890"},{"key":"e_1_2_1_34_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889893001219"},{"key":"e_1_2_1_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9539960"},{"key":"e_1_2_1_36_2","doi-asserted-by":"publisher","DOI":"10.1107\/S002188980600731X"},{"key":"e_1_2_1_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar800147t"},{"key":"e_1_2_1_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp052465n"},{"key":"e_1_2_1_39_2","doi-asserted-by":"publisher","DOI":"10.1080\/01442350802102387"},{"key":"e_1_2_1_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ct700270d"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchir.20761","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.20761","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,11,21]],"date-time":"2023-11-21T00:57:21Z","timestamp":1700528241000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.20761"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,7,30]]},"references-count":39,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2010,5,5]]}},"alternative-id":["10.1002\/chir.20761"],"URL":"https:\/\/doi.org\/10.1002\/chir.20761","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"value":"0899-0042","type":"print"},{"value":"1520-636X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,7,30]]}}}