{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,5]],"date-time":"2026-06-05T10:50:20Z","timestamp":1780656620512,"version":"3.54.1"},"reference-count":54,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2021,11,24]],"date-time":"2021-11-24T00:00:00Z","timestamp":1637712000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"International Graduate School AGRIPOLY supported by the European Regional Development Fund (ERDF) and the Federal State Saxony-Anhalt","award":["AGRIPOLY"],"award-info":[{"award-number":["AGRIPOLY"]}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["DFG-Graduate College GRK 2670 (German research foundation \u2013 project ID 43649874, TP B2, RTG 2670"],"award-info":[{"award-number":["DFG-Graduate College GRK 2670 (German research foundation \u2013 project ID 43649874, TP B2, RTG 2670"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100010661","name":"Horizon 2020","doi-asserted-by":"publisher","award":["BAT4EVER in European Union in the scope of H2020-LC-BAT-2020-3"],"award-info":[{"award-number":["BAT4EVER in European Union in the scope of H2020-LC-BAT-2020-3"]}],"id":[{"id":"10.13039\/100010661","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Carbonyl-centered hydrogen bonds with various strength and geometries are often exploited in materials to embed dynamic and adaptive properties, with the use of thiocarbonyl groups as hydrogen-bonding acceptors remaining only scarcely investigated. We herein report a comparative study of C2=O and C2=S barbiturates in view of their differing hydrogen bonds, using the 5,5-disubstituted barbiturate B and the thiobarbiturate TB as model compounds. Owing to the different hydrogen-bonding strength and geometries of C2=O vs. C2=S, we postulate the formation of different hydrogen-bonding patterns in C2=S in comparison to the C2=O in conventional barbiturates. To study differences in their association in solution, we conducted concentration- and temperature-dependent NMR experiments to compare their association constants, Gibbs free energy of association \u2206Gassn., and the coalescence behavior of the N-H\u2027\u2027\u2027S=C bonded assemblies. In Langmuir films, the introduction of C2=S suppressed 2D crystallization when comparing B and TB using Brewster angle microscopy, also revealing a significant deviation in morphology. When embedded into a hydrophobic polymer such as polyisobutylene, a largely different rheological behavior was observed for the barbiturate-bearing PB compared to the thiobarbiturate-bearing PTB polymers, indicative of a stronger hydrogen bonding in the thioanalogue PTB. We therefore prove that H-bonds, when affixed to a polymer, here the thiobarbiturate moieties in PTB, can reinforce the nonpolar PIB matrix even better, thus indicating the formation of stronger H-bonds among the thiobarbiturates in polymers in contrast to the effects observed in solution.<\/jats:p>","DOI":"10.3390\/ijms222312679","type":"journal-article","created":{"date-parts":[[2021,11,30]],"date-time":"2021-11-30T04:48:37Z","timestamp":1638247717000},"page":"12679","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Comparing C2=O and C2=S Barbiturates: Different Hydrogen-Bonding Patterns of Thiobarbiturates in Solution and the Solid State"],"prefix":"10.3390","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2602-2350","authenticated-orcid":false,"given":"Chenming","family":"Li","sequence":"first","affiliation":[{"name":"Macromolecular Chemistry, Institute of Chemistry, Martin-Luther University Halle-Wittenberg, Von-Danckelmann-Platz 4, D-06120 Halle (Saale), Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Philipp","family":"Hilgeroth","sequence":"additional","affiliation":[{"name":"Macromolecular Chemistry, Institute of Chemistry, Martin-Luther University Halle-Wittenberg, Von-Danckelmann-Platz 4, D-06120 Halle (Saale), Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nazmul","family":"Hasan","sequence":"additional","affiliation":[{"name":"Physical Chemistry, Institute of Chemistry, Martin-Luther University Halle-Wittenberg, Von-Danckelmann-Platz 4, D-06120 Halle (Saale), Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dieter","family":"Str\u00f6hl","sequence":"additional","affiliation":[{"name":"Organic Chemistry, Institute of Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes-Str. 2, 06120 Halle (Saale), Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8571-5985","authenticated-orcid":false,"given":"J\u00f6rg","family":"Kressler","sequence":"additional","affiliation":[{"name":"Physical Chemistry, Institute of Chemistry, Martin-Luther University Halle-Wittenberg, Von-Danckelmann-Platz 4, D-06120 Halle (Saale), Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3834-5445","authenticated-orcid":false,"given":"Wolfgang H.","family":"Binder","sequence":"additional","affiliation":[{"name":"Macromolecular Chemistry, Institute of Chemistry, Martin-Luther University Halle-Wittenberg, Von-Danckelmann-Platz 4, D-06120 Halle (Saale), Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,11,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1637","DOI":"10.1351\/PAC-REC-10-01-02","article-title":"Definition of the hydrogen bond (IUPAC Recommendations 2011)","volume":"83","author":"Arunan","year":"2011","journal-title":"Pure Appl. 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