{"title":"Functionality-Matched Semicarbazone Reagents Allow Access to X-ray Quality Crystals and Solids of Diverse Organic Molecules.","authors":"Emily R Sherman, Jeffrey S Johnson","doi":"10.1021/acs.orglett.6c01328","DOIUrl":null,"url":null,"abstract":"<p><p>A flexible approach to crystalline compounds was developed: lipophilic structures of interest were connected to pro-crystalline semicarbazone reagents via copper-catalyzed azide-alkyne cycloaddition or Brønsted-Lowry acid-base reactions. A variety of lipophilic structures, including esters, carbamates, acids and amines were converted into crystalline solids as determined by powder X-ray diffraction (mp 134 to >240 °C). Single crystal X-ray diffraction revealed hydrogen-bond interactions between the semicarbazone and charged ammonium or acetate groups that may aid in ordering the crystals.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"6048-6053"},"PeriodicalIF":5.0000,"publicationDate":"2027-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.6c01328","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A flexible approach to crystalline compounds was developed: lipophilic structures of interest were connected to pro-crystalline semicarbazone reagents via copper-catalyzed azide-alkyne cycloaddition or Brønsted-Lowry acid-base reactions. A variety of lipophilic structures, including esters, carbamates, acids and amines were converted into crystalline solids as determined by powder X-ray diffraction (mp 134 to >240 °C). Single crystal X-ray diffraction revealed hydrogen-bond interactions between the semicarbazone and charged ammonium or acetate groups that may aid in ordering the crystals.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.