European Journal of Organic Chemistry最新文献_第2页

Front Cover: Methanol-Mediated One-Pot Transformation of Benzonitriles to Five and Six-Membered Heterocycles: Synthesis and Mechanistic Approach (Eur. J. Org. Chem. 41/2024) 封面：甲醇介导的苯甲腈向五元和六元杂环的一锅转化：合成与机理方法（欧洲有机化学杂志 41/2024）

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-11 DOI: 10.1002/ejoc.202484101

Nikos Siakavaras, Michael G. Kallitsakis, Evangelos G. Bakalbassis, Michael M. Sigalas, Ioannis N. Lykakis

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Synthesis and EPR Studies of Zinc and Copper Tris(2‐pyridylmethyl)amines (TPMA) Metal Complexes Containing TEMPO Functionalities 含 TEMPO 功能的锌和铜三(2-吡啶基甲基)胺 (TPMA) 金属配合物的合成与 EPR 研究

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-11 DOI: 10.1002/ejoc.202400384

Elena Badetti , Vega Lloveras , Melvin Raulin , Francesca A. Scaramuzzo , Jaume Veciana , José Vidal‐Gancedo , Giulia Licini , Cristiano Zonta

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Addition of Sydnones to para‐Quinone Methides: Selective 1,6‐Additions and Oxidative C−H Functionalizations Sydnones 与对位醌甲酰胺的加成：选择性 1,6-加成和氧化 C-H 功能化

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-11 DOI: 10.1002/ejoc.202400703

Lavina Gladis Serrao, S. Naveenkumar, Mahagundappa R. Maddani

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Acceptor End‐functionalization of Naphthalenediimide Bithiophene Oligomers 萘二亚胺双噻吩低聚物的受体端功能化

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-09 DOI: 10.1002/ejoc.202400751

Rukiya Matsidik, Hartmut Komber, Paul Burkhard, Daniel Beer, Carsten Deibel, Michael Sommer

{"title":"Acceptor End‐functionalization of Naphthalenediimide Bithiophene Oligomers","authors":"Rukiya Matsidik, Hartmut Komber, Paul Burkhard, Daniel Beer, Carsten Deibel, Michael Sommer","doi":"10.1002/ejoc.202400751","DOIUrl":"https://doi.org/10.1002/ejoc.202400751","url":null,"abstract":"Oligomeric materials combine advantageous properties of both their small molecule and polymeric counterparts. Utilizing oligomers as non‐fullerene acceptors (NFAs) has been shown to be extremely useful for the development of organic solar cells with high efficiency, reproducible performance and long‐term stability. Here we report on two series of synthetically simple acceptor‐terminated oligomers A−T2‐(NDI−T2)n‐A with naphthalene diimide (NDI) and bithiophene (T2) cores up to the trimer (n =1,2,3). Termination of the oligomers is done using the strong acceptors (A) dicyanomethylene‐indanone (IC) and rhodanine (RD). Upon acceptor termination in the presence of piperidine (pip) as base, oligomers with pip‐substituted tricyclic end groups are obtained in high yield. We investigate the effect of oligomer length and acceptor end group on opto‐electronic properties and crystallinity. Both IC‐ and RD‐termination increase electron affinity compared to the parent, non‐functionalized cores. UV‐vis absorption in solution slightly redshifts as the chain length increases without showing a distinct aggregation. Asymmetric termination with hexylphenyl‐substituted indacenodithiophene (IDT) and IC is also possible. All symmetric oligomers show a strong tendency for crystallization, with the oligomer having the tricyclic end group exhibiting the highest melting enthalpy and temperature. The asymmetric IDT−T2‐NDI−T2‐IC oligomer is amorphous.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142596778","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Structurally Innovative Benzimidazole‐fused Ionic Organoselenium Compounds: Prevalence of Se···N/Se Chalcogen Bonds with the Selenocyanate Receptor 结构新颖的苯并咪唑融合离子有机硒化合物：Se--N/Se钙原键与硒氰酸酯受体的普遍性

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-09 DOI: 10.1002/ejoc.202401245

Krishna Pada Bhabak, Kaustav Banerjee, Abu Sufian

{"title":"Structurally Innovative Benzimidazole‐fused Ionic Organoselenium Compounds: Prevalence of Se···N/Se Chalcogen Bonds with the Selenocyanate Receptor","authors":"Krishna Pada Bhabak, Kaustav Banerjee, Abu Sufian","doi":"10.1002/ejoc.202401245","DOIUrl":"https://doi.org/10.1002/ejoc.202401245","url":null,"abstract":"The non‐covalent interactions in molecules play important roles towards their applications in various aspects such as molecular recognition, catalysis, supramolecular chemistry, structural biology, pharmacology etc. Interestingly, among various non‐bonding interactions, chalcogen bonding (ChB) has been extensively studied in different facets of crystal engineering over the last several years. The present study demonstrates the presence of Se···N or Se···Se ChB in the benzimidazole‐fused cyclic selenazonium selenocyanates (6‐8), cyclic selenazinium selenocyanates (9‐10) and the acyclic benzimidazolium analogs having two different types of selenocyanate units (11‐12). The final organoselenium compounds were synthesized from benzimidazole in several steps in reasonably good yields. The single crystal X‐ray structures of the compounds revealed that both the N atom and Se atom of the negatively charged SeCN unit act as ChB acceptors in building the Se···N or Se···Se ChB interactions along with the additional hydrogen bonding (HB) interactions. Moreover, the structural optimization and natural bond orbital (NBO) analyses were carried out using density functional theory (DFT) to calculate the natural charges on different Se centers and the strength of second‐order perturbation energy (E2) for the ChB interactions. Finally, electrostatic potential surface (SEP) of the compounds was developed to visualize the formation of σ‐holes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"71 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142596796","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Aryl Radicals Generated from Aryl Pinacol Boronates Modify Peptides and Proteins 芳基频哪醇硼酸酯产生的芳基自由基可修饰肽和蛋白质

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-09 DOI: 10.1002/ejoc.202401246

Haoyu Chen, Dongqing Wu, Julian Holzinger, Rainer Götz, Dorian Didier, Anne K Schütz, Sabine Schneider, Pavel Kielkowski

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Batch to Continuous Flow Visible‐Light Photooxidations Using Alumina Supported Hydroxyanthraquinones 使用氧化铝支撑的羟基蒽醌进行从间歇到连续流的可见光光氧化反应

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-09 DOI: 10.1002/ejoc.202400634

Yahya Al Ayi, Augustin Pirenam Atakpa, Cylia Arab, Maxime Lancel, Zacharias Amara

引用次数: 0

Benzofuroxan‐Based Energetic Materials with Alternating Nitro and Hydroxyl Groups: Synthesis, Characterization, and Energetic Properties 具有交替硝基和羟基的苯并呋喃基高能材料：合成、表征和能量特性

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-09 DOI: 10.1002/ejoc.202400794

Atharva Tiwari, Krishna Pandey, Priyanka Das, Vikas D. Ghule, Dheeraj Kumar

{"title":"Benzofuroxan‐Based Energetic Materials with Alternating Nitro and Hydroxyl Groups: Synthesis, Characterization, and Energetic Properties","authors":"Atharva Tiwari, Krishna Pandey, Priyanka Das, Vikas D. Ghule, Dheeraj Kumar","doi":"10.1002/ejoc.202400794","DOIUrl":"https://doi.org/10.1002/ejoc.202400794","url":null,"abstract":"Due to its good stability, density and oxygen balance, the benzofuroxan fused ring framework has attracted particular attention in the field of high energy density materials. The planar structure of the benzofuroxan facilitates the straightforward derivatization with explosophores and contributes to molecular stability. In this work, a benzofuroxan scaffold was utilized to develop a highly dense energetic material, namely 5,7‐dihydroxy‐4,6‐dinitrobenzo[c][1,2,5]oxadiazole 1‐oxide (DHDNBF). The successive inclusion of explosophores like nitro (−NO2) and oxidative functionality like hydroxyl (−OH) on benzofuroxan resulted in an impressive density (ρ=1.91 g cm−3) and a positive oxygen balance (6.20 %) in DHDNBF (2). Furthermore, the hydroxy groups on DHDNBF enable the formation of dicationic energetic salts 3–7, contributing to additional modifications in the overall performance. Energetic salts 3, 4, and 5 exhibit significantly higher densities ranging from 1.84 (5) to 1.87 (3) g cm−3 and possess a favorable oxygen balance approaching zero or equal to zero. A marked improvement in thermal stabilities was observed in all the energetic salts (3–7) compared to their neutral counterparts, DHDNBF. Energetic salts 4 (Dv=8459 m s−1, P=32.10 GPa) and 5 (Dv=8539 m s−1, P=30.37 GPa) possess good energetic performance, comparable to that of well‐known explosives such as LLM‐105 (Dv=8560 m s−1, P=33.4 GPa). Overall, the favorable characteristics of energetic salts 4 and 5 make them potential candidates for use as benzofuroxan‐based secondary and primary explosives, respectively, in various military and civilian applications.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"35 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142596782","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Homobarrelenones: Versatile Building Blocks for the Construction of Novel and Structurally Diverse Scaffolds 同巴利酮：构建结构多样的新型支架的多功能构件

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-08 DOI: 10.1002/ejoc.202400887

Valeria Lucero, Hugo do Carmo, Gabriel Fernández, Mauricio Cabrera, Macarena Eugui, Guillermo Moyna

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Intermolecular Carbanion Attack on Nitro vs. Carbonyl Group: Experimental and Computational Studies 硝基与羰基的分子间碳化作用：实验和计算研究

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-08 DOI: 10.1002/ejoc.202400612

Krisztián Bíró, Miklós Nyerges, Imre Pápai, Dániel Csókás

引用次数: 0