{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,22]],"date-time":"2026-01-22T15:47:39Z","timestamp":1769096859898,"version":"3.49.0"},"reference-count":139,"publisher":"Wiley","issue":"26","license":[{"start":{"date-parts":[[2020,4,21]],"date-time":"2020-04-21T00:00:00Z","timestamp":1587427200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100011033","name":"Agencia Estatal de Investigaci\u00f3n","doi-asserted-by":"publisher","award":["CTQ2016-78423-R"],"award-info":[{"award-number":["CTQ2016-78423-R"]}],"id":[{"id":"10.13039\/501100011033","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100011033","name":"Agencia Estatal de Investigaci\u00f3n","doi-asserted-by":"publisher","award":["RTI2018-098795-A-I00"],"award-info":[{"award-number":["RTI2018-098795-A-I00"]}],"id":[{"id":"10.13039\/501100011033","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010801","name":"Xunta de Galicia","doi-asserted-by":"publisher","award":["ED431C 2017\/25"],"award-info":[{"award-number":["ED431C 2017\/25"]}],"id":[{"id":"10.13039\/501100010801","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010801","name":"Xunta de Galicia","doi-asserted-by":"publisher","award":["2019-2022, ED431G 2019\/03"],"award-info":[{"award-number":["2019-2022, ED431G 2019\/03"]}],"id":[{"id":"10.13039\/501100010801","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100014440","name":"Ministerio de Ciencia, Innovaci\u00f3n y Universidades","doi-asserted-by":"publisher","award":["RYC-2016-20335"],"award-info":[{"award-number":["RYC-2016-20335"]}],"id":[{"id":"10.13039\/100014440","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100014440","name":"Ministerio de Ciencia, Innovaci\u00f3n y Universidades","doi-asserted-by":"publisher","award":["CTQ2016-81797-REDC"],"award-info":[{"award-number":["CTQ2016-81797-REDC"]}],"id":[{"id":"10.13039\/100014440","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2020,5,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Cyclic peptides with disc\u2010shaped structures have emerged as potent building blocks for the preparation of new biomaterials in fields ranging from biological to material science. In this work, we analyze in depth the self\u2010assembling properties of a new type of cyclic peptides based on the alternation of \u03b1\u2010residues and cyclic \u03b4\u2010amino acids (\u03b1,\u03b4\u2010CPs). To examine the preferred stacking properties adopted by cyclic peptides bearing this type of amino acids, we carried out a synergistic in vitro\/in silico approximation by using simple dimeric models and then extended to nanotubes. Although these new cyclic peptides (\u03b1,\u03b4\u2010CPs) can interact either in a parallel or antiparallel fashion, our results confirm that although the parallel \u03b2\u2010sheet is more stable, it can be switched to the antiparallel stacking by choosing residues that can establish favorable cross\u2010strand interactions. Moreover, the subsequent comparison by using the same methodology but applied to \u03b1,\u03b3\u2010CPs models, up to the moment assumed as antiparallel\u2010like <jats:sc>d,l<\/jats:sc>\u2010\u03b1\u2010CPs, led to unforeseen conclusions that put into question preliminary conjectures about these systems. Surprisingly, they tend to adopt a parallel \u03b2\u2010sheet directed by the skeleton interactions. These results imply a change of paradigm with respect to cyclic peptide designs that should be considered for dimers and nanotubes.<\/jats:p>","DOI":"10.1002\/chem.201905554","type":"journal-article","created":{"date-parts":[[2020,1,30]],"date-time":"2020-01-30T16:22:15Z","timestamp":1580401335000},"page":"5846-5858","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Parallel Versus Antiparallel \u03b2\u2010Sheet Structure in Cyclic Peptide Hybrids Containing \u03b3\u2010 or \u03b4\u2010Cyclic Amino Acids"],"prefix":"10.1002","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7114-1781","authenticated-orcid":false,"given":"Mart\u00edn","family":"Calvelo","sequence":"first","affiliation":[{"name":"Centro Singular de Investigaci\u00f3n en Qu\u00edmica Biol\u00f3xica e, Materiais Moleculares (CIQUS) Departamento de Qu\u00edmica Org\u00e1nica Universidade de Santiago de Compostela  15782 Santiago de Compostela Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5309-9126","authenticated-orcid":false,"given":"Alejandro","family":"Lamas","sequence":"additional","affiliation":[{"name":"Centro Singular de Investigaci\u00f3n en Qu\u00edmica Biol\u00f3xica e, Materiais Moleculares (CIQUS) Departamento de Qu\u00edmica Org\u00e1nica Universidade de Santiago de Compostela  15782 Santiago de Compostela Spain"}]},{"given":"Arcadio","family":"Guerra","sequence":"additional","affiliation":[{"name":"Centro Singular de Investigaci\u00f3n en Qu\u00edmica Biol\u00f3xica e, Materiais Moleculares (CIQUS) Departamento de Qu\u00edmica Org\u00e1nica Universidade de Santiago de Compostela  15782 Santiago de Compostela Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2992-5555","authenticated-orcid":false,"given":"Manuel","family":"Amor\u00edn","sequence":"additional","affiliation":[{"name":"Centro Singular de Investigaci\u00f3n en Qu\u00edmica Biol\u00f3xica e, Materiais Moleculares (CIQUS) Departamento de Qu\u00edmica Org\u00e1nica Universidade de Santiago de Compostela  15782 Santiago de Compostela Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5274-3928","authenticated-orcid":false,"given":"Rebeca","family":"Garcia\u2010Fandino","sequence":"additional","affiliation":[{"name":"Centro Singular de Investigaci\u00f3n en Qu\u00edmica Biol\u00f3xica e, Materiais Moleculares (CIQUS) Departamento de Qu\u00edmica Org\u00e1nica Universidade de Santiago de Compostela  15782 Santiago de Compostela Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5842-7504","authenticated-orcid":false,"given":"Juan R.","family":"Granja","sequence":"additional","affiliation":[{"name":"Centro Singular de Investigaci\u00f3n en Qu\u00edmica Biol\u00f3xica e, Materiais Moleculares (CIQUS) Departamento de Qu\u00edmica Org\u00e1nica Universidade de Santiago de Compostela  15782 Santiago de Compostela Spain"}]}],"member":"311","published-online":{"date-parts":[[2020,4,21]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1070821"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1038\/nbt874"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.893"},{"key":"e_1_2_7_5_1","unstructured":"\u00a0"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-biochem-062917-012541"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.addr.2016.08.006"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmat4474"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00164H"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.actamat.2012.10.046"},{"key":"e_1_2_7_11_1","unstructured":"\u00a0"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010316)40:6<988::AID-ANIE9880>3.0.CO;2-N"},{"key":"e_1_2_7_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010316)113:6<1016::AID-ANGE10160>3.0.CO;2-8"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/B805753M"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35172b"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB00351J"},{"key":"e_1_2_7_16_1","unstructured":"\u00a0"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201402975"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/jbm.a.35638"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC02997G"},{"key":"e_1_2_7_20_1","unstructured":"\u00a0"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.5b00672"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1088\/0957-4484\/24\/19\/195103"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/bm4008293"},{"key":"e_1_2_7_24_1","unstructured":"\u00a0"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.2174\/1568026614666141215143431"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201508714"},{"key":"e_1_2_7_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201508714"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601830"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5NR06804E"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biomac.7b01491"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.7b00154"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-04763-y"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC01233D"},{"key":"e_1_2_7_33_1","unstructured":"\u00a0"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5PY01313E"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsmacrolett.7b00728"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201811910"},{"key":"e_1_2_7_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201811910"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC00756C"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsmacrolett.9b00538"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8NH00009C"},{"key":"e_1_2_7_40_1","unstructured":"\u00a0"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1038\/366324a0"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja953070s"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/ma60037a011"},{"key":"e_1_2_7_44_1","unstructured":"\u00a0"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199500951"},{"key":"e_1_2_7_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951070115"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2836(82)90163-2"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1023\/A:1007908728919"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/qua.22308"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC00846E"},{"key":"e_1_2_7_50_1","unstructured":"\u00a0"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199500931"},{"key":"e_1_2_7_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951070114"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja981485i"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.3247578"},{"key":"e_1_2_7_54_1","unstructured":"\u00a0"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00092a079"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00102a054"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19940770607"},{"key":"e_1_2_7_58_1","unstructured":"\u00a0"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0296273"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja904548q"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja410901r"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.5b03445"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6NR08174F"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200701059"},{"key":"e_1_2_7_65_1","unstructured":"\u00a0"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob26612a"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.201200488"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b02942"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00871"},{"key":"e_1_2_7_70_1","unstructured":"\u00a0"},{"key":"e_1_2_7_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19970800116"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja972786f"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1039\/B610858J"},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/psc.1206"},{"key":"e_1_2_7_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/bip.22177"},{"key":"e_1_2_7_76_1","unstructured":"\u00a0"},{"key":"e_1_2_7_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20011217)40:24<4635::AID-ANIE4635>3.0.CO;2-D"},{"key":"e_1_2_7_77_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20011217)113:24<4771::AID-ANGE4771>3.0.CO;2-Z"},{"key":"e_1_2_7_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700522"},{"key":"e_1_2_7_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201900802"},{"key":"e_1_2_7_80_1","unstructured":"\u00a0"},{"key":"e_1_2_7_81_2","first-page":"1","author":"Wada A.","year":"1976","journal-title":"Adv. Biophys."},{"key":"e_1_2_7_82_2","doi-asserted-by":"publisher","DOI":"10.1038\/273443a0"},{"key":"e_1_2_7_83_1","unstructured":"\u00a0"},{"key":"e_1_2_7_84_2","doi-asserted-by":"publisher","DOI":"10.1039\/b911247m"},{"key":"e_1_2_7_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2063082"},{"key":"e_1_2_7_86_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC03187G"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.1397-002X.2000.00823.x"},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b03732"},{"key":"e_1_2_7_89_1","unstructured":"\u00a0"},{"key":"e_1_2_7_90_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-chembioeng-073009-100847"},{"key":"e_1_2_7_91_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules201119705"},{"key":"e_1_2_7_92_2","volume-title":"Drug Delivery Strategies for Poorly Water-Soluble Drugs","author":"Douroumis D.","year":"2012"},{"key":"e_1_2_7_93_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC02276C"},{"key":"e_1_2_7_94_1","unstructured":"\u00a0"},{"key":"e_1_2_7_95_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200501555"},{"key":"e_1_2_7_95_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200501555"},{"key":"e_1_2_7_96_2","doi-asserted-by":"publisher","DOI":"10.1039\/b703659k"},{"key":"e_1_2_7_97_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0518885"},{"key":"e_1_2_7_98_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC47400C"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201304200"},{"key":"e_1_2_7_100_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203213"},{"key":"e_1_2_7_101_1","unstructured":"\u00a0"},{"key":"e_1_2_7_102_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CP02327E"},{"key":"e_1_2_7_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.6b00202"},{"key":"e_1_2_7_104_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CP04200C"},{"key":"e_1_2_7_105_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp400796n"},{"key":"e_1_2_7_106_2","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pcbi.1002647"},{"key":"e_1_2_7_107_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2sc21068a"},{"key":"e_1_2_7_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp910919k"},{"key":"e_1_2_7_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja903400n"},{"key":"e_1_2_7_110_1","unstructured":"The O\u22c5\u22c5\u22c5H\u2212N and C=O\u22c5\u22c5\u22c5H angles obtained from the crystal structures of \u03b1-d l-CPs (c-[(l-MeN-Ala-d-Phe-)3] or \u03b1 \u03b3-CPs (c-[(d-Phe-1R 3S-MeN-Ach-)3]) are 164.9 and 149 and 153\u2013155 and 145\u2013146\u00b0 respectively. See references\u2005[14a] and [17a]."},{"key":"e_1_2_7_111_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar00105a004"},{"key":"e_1_2_7_112_1","unstructured":"\u00a0"},{"key":"e_1_2_7_113_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsb.2004.08.002"},{"key":"e_1_2_7_114_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc43837f"},{"key":"e_1_2_7_115_2","doi-asserted-by":"publisher","DOI":"10.1006\/abbi.1997.0137"},{"key":"e_1_2_7_116_2","doi-asserted-by":"publisher","DOI":"10.1007\/s12154-009-0027-5"},{"key":"e_1_2_7_117_2","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(89)90046-8"},{"key":"e_1_2_7_118_1","unstructured":"\u00a0"},{"key":"e_1_2_7_119_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.464304"},{"key":"e_1_2_7_120_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_2_7_121_1","unstructured":"\u00a0"},{"key":"e_1_2_7_122_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.3382344"},{"key":"e_1_2_7_123_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21759"},{"key":"e_1_2_7_124_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.5b01066"},{"key":"e_1_2_7_125_1","unstructured":"\u00a0"},{"key":"e_1_2_7_126_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00267a063"},{"key":"e_1_2_7_127_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.476673"},{"key":"e_1_2_7_128_1","unstructured":"\u00a0"},{"key":"e_1_2_7_129_2","doi-asserted-by":"publisher","DOI":"10.1080\/00268977000101561"},{"key":"e_1_2_7_130_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.472902"},{"key":"e_1_2_7_131_1","unstructured":"Gaussian\u200516 Revision\u2005B.01 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone G.\u2005A. Petersson H. Nakatsuji X. Li M. Caricato A.\u2005V. Marenich J. Bloino B.\u2005G. Janesko R. Gomperts B. Mennucci H.\u2005P. Hratchian J.\u2005V. Ortiz A.\u2005F. Izmaylov J.\u2005L. Sonnenberg D. Williams-Young F. Ding F. Lipparini F. Egidi J. Goings B. Peng A. Petrone T. Henderson D. Ranasinghe V.\u2005G. Zakrzewski J. Gao N. Rega G. Zheng W. Liang M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven K. Throssell J.\u2005A. Montgomery \u2005Jr. J.\u2005E. Peralta F. Ogliaro M.\u2005J. Bearpark J.\u2005J. Heyd E.\u2005N. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov T.\u2005A. Keith R. Kobayashi J. Normand K. Raghavachari A.\u2005P. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi J.\u2005M. Millam M. Klene C. Adamo R. Cammi J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma O. Farkas J.\u2005B. Foresman D.\u2005J. Fox Gaussian Inc. Wallingford CT 2016."},{"key":"e_1_2_7_132_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00894-012-1667-x"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201905554","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201905554","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.201905554","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201905554","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T16:55:40Z","timestamp":1760288140000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201905554"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,4,21]]},"references-count":139,"journal-issue":{"issue":"26","published-print":{"date-parts":[[2020,5,7]]}},"alternative-id":["10.1002\/chem.201905554"],"URL":"https:\/\/doi.org\/10.1002\/chem.201905554","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,4,21]]},"assertion":[{"value":"2019-12-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-04-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}