{"title":"Acyclic cucurbit[<i>n</i>]uril bearing alkyl sulfate ionic groups.","authors":"Christian Akakpo, Peter Y Zavalij, Lyle Isaacs","doi":"10.3762/bjoc.21.55","DOIUrl":null,"url":null,"abstract":"<p><p>We report the synthesis and characterization of a new acyclic cucurbit[<i>n</i>]uril (CB[<i>n</i>]) host <b>C1</b> that features four alkyl sulfate ionic groups. The X-ray crystal structure of the <b>C1·Me</b> <b><sub>6</sub></b> <b>CHDA</b> complex is reported. Host <b>C1</b> is significantly less soluble in water (4 mM) compared to the analogous acyclic CB[<i>n</i>] host <b>M1</b> which features sulfonate ionic groups (346 mM). Host <b>C1</b> does not undergo significant self-association according to the results of <sup>1</sup>H NMR dilution experiments. The molecular recognition behavior of the hosts <b>C1</b> and <b>M1</b> toward a panel of seven ammonium ions was explored by <sup>1</sup>H NMR spectroscopy and isothermal titration calorimetry (ITC). We find that <b>C1</b> generally binds slightly more tightly than <b>M1</b> toward a specific guest. <b>C1</b> binds more tightly to quaternary ammonium guests compared to the corresponding primary ammonium ions.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"717-726"},"PeriodicalIF":2.2000,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11973588/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.21.55","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
We report the synthesis and characterization of a new acyclic cucurbit[n]uril (CB[n]) host C1 that features four alkyl sulfate ionic groups. The X-ray crystal structure of the C1·Me6CHDA complex is reported. Host C1 is significantly less soluble in water (4 mM) compared to the analogous acyclic CB[n] host M1 which features sulfonate ionic groups (346 mM). Host C1 does not undergo significant self-association according to the results of 1H NMR dilution experiments. The molecular recognition behavior of the hosts C1 and M1 toward a panel of seven ammonium ions was explored by 1H NMR spectroscopy and isothermal titration calorimetry (ITC). We find that C1 generally binds slightly more tightly than M1 toward a specific guest. C1 binds more tightly to quaternary ammonium guests compared to the corresponding primary ammonium ions.
期刊介绍：
The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry.
The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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