二羧酰胺的单晶结构分析：杂原子对甲酰胺基团氢键的影响

IF 2.4 4区材料科学 Q2 CRYSTALLOGRAPHY

Crystals Pub Date : 2024-09-14 DOI:10.3390/cryst14090811

Abdulrahman Mohabbat, Jasmin Salama, Philipp Seiffert, István Boldog, Christoph Janiak

{"title":"二羧酰胺的单晶结构分析：杂原子对甲酰胺基团氢键的影响","authors":"Abdulrahman Mohabbat, Jasmin Salama, Philipp Seiffert, István Boldog, Christoph Janiak","doi":"10.3390/cryst14090811","DOIUrl":null,"url":null,"abstract":"This research examines how heteroatoms in a six- or five-membered pyridine, thiophene or furan ring spacer between two carboxamide groups influence the hydrogen bonding for advancements in supramolecular chemistry and drug development. The solvent-free crystal structures of 3,5-pyridinedicarboxamide (PDC), 2,5-thiophenedicarboxamide (TDC) and 2,5-furandicarboxamide (FDC-subl, crystallized by sublimation), and the monohydrate structure of FDC-solv (crystallized from methanol) are described with the hydrogen-bonding analyzed by the Etter graph-set notation. The carbon atoms of the amide groups form an angle of 121° in PDC, 151° in TDC, 137° in FDC-solv and 135° in FDC-subl with the ring centroid. Only in the structure of PDC does the heteroatom act as an H-bond acceptor as part of a C11(6) chain. In TDC and FDC, the heteroatoms do not interact with the amide -NH2 groups.","PeriodicalId":10855,"journal":{"name":"Crystals","volume":"1 1","pages":""},"PeriodicalIF":2.4000,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Single-Crystal Structure Analysis of Dicarboxamides: Impact of Heteroatoms on Hydrogen Bonding of Carboxamide Groups\",\"authors\":\"Abdulrahman Mohabbat, Jasmin Salama, Philipp Seiffert, István Boldog, Christoph Janiak\",\"doi\":\"10.3390/cryst14090811\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"This research examines how heteroatoms in a six- or five-membered pyridine, thiophene or furan ring spacer between two carboxamide groups influence the hydrogen bonding for advancements in supramolecular chemistry and drug development. The solvent-free crystal structures of 3,5-pyridinedicarboxamide (PDC), 2,5-thiophenedicarboxamide (TDC) and 2,5-furandicarboxamide (FDC-subl, crystallized by sublimation), and the monohydrate structure of FDC-solv (crystallized from methanol) are described with the hydrogen-bonding analyzed by the Etter graph-set notation. The carbon atoms of the amide groups form an angle of 121° in PDC, 151° in TDC, 137° in FDC-solv and 135° in FDC-subl with the ring centroid. Only in the structure of PDC does the heteroatom act as an H-bond acceptor as part of a C11(6) chain. In TDC and FDC, the heteroatoms do not interact with the amide -NH2 groups.\",\"PeriodicalId\":10855,\"journal\":{\"name\":\"Crystals\",\"volume\":\"1 1\",\"pages\":\"\"},\"PeriodicalIF\":2.4000,\"publicationDate\":\"2024-09-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Crystals\",\"FirstCategoryId\":\"88\",\"ListUrlMain\":\"https://doi.org/10.3390/cryst14090811\",\"RegionNum\":4,\"RegionCategory\":\"材料科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CRYSTALLOGRAPHY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Crystals","FirstCategoryId":"88","ListUrlMain":"https://doi.org/10.3390/cryst14090811","RegionNum":4,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CRYSTALLOGRAPHY","Score":null,"Total":0}

引用次数: 0

摘要

这项研究探讨了两个羧酰胺基团之间的六元或五元吡啶、噻吩或呋喃环间隔中的杂原子如何影响氢键，从而推动超分子化学和药物开发。本研究采用埃特图集符号描述了 3,5-吡啶二甲酰胺（PDC）、2,5-噻吩二甲酰胺（TDC）和 2,5-呋喃二甲酰胺（FDC-subl，升华结晶）的无溶剂晶体结构，以及 FDC-solv（甲醇结晶）的一水合物结构，并对氢键进行了分析。在 PDC、TDC、FDC-solv 和 FDC-subl 中，酰胺基团的碳原子与环中心点的夹角分别为 121°、151°、137°和 135°。只有在 PDC 结构中，杂原子才作为 C11(6) 链的一部分而充当氢键受体。在 TDC 和 FDC 中，杂原子与酰胺 -NH2 基团没有相互作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Single-Crystal Structure Analysis of Dicarboxamides: Impact of Heteroatoms on Hydrogen Bonding of Carboxamide Groups

This research examines how heteroatoms in a six- or five-membered pyridine, thiophene or furan ring spacer between two carboxamide groups influence the hydrogen bonding for advancements in supramolecular chemistry and drug development. The solvent-free crystal structures of 3,5-pyridinedicarboxamide (PDC), 2,5-thiophenedicarboxamide (TDC) and 2,5-furandicarboxamide (FDC-subl, crystallized by sublimation), and the monohydrate structure of FDC-solv (crystallized from methanol) are described with the hydrogen-bonding analyzed by the Etter graph-set notation. The carbon atoms of the amide groups form an angle of 121° in PDC, 151° in TDC, 137° in FDC-solv and 135° in FDC-subl with the ring centroid. Only in the structure of PDC does the heteroatom act as an H-bond acceptor as part of a C11(6) chain. In TDC and FDC, the heteroatoms do not interact with the amide -NH2 groups.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Crystals CRYSTALLOGRAPHYMATERIALS SCIENCE, MULTIDIS-MATERIALS SCIENCE, MULTIDISCIPLINARY

CiteScore

4.20

自引率

11.10%

发文量

1527

审稿时长

16.12 days

期刊介绍： Crystals (ISSN 2073-4352) is an open access journal that covers all aspects of crystalline material research. Crystals can act as a reference, and as a publication resource, to the community. It publishes reviews, regular research articles, and short communications. Our aim is to encourage scientists to publish their experimental and theoretical results in as much detail as possible. Therefore, there is no restriction on article length. Full experimental details must be provided to enable the results to be reproduced. Crystals provides a forum for the advancement of our understanding of the nucleation, growth, processing, and characterization of crystalline materials. Their mechanical, chemical, electronic, magnetic, and optical properties, and their diverse applications, are all considered to be of importance.