Leysan I. Gallyamova , Alfiya R. Bayguzina , Ilfir R. Ramazanov
Synthesis of adamantyl‐containing cyclic ketals, spirooxazolidines, spiroimidazolidines, spirooxathiolanes, spirodithiolanes, spirooxazines, spirobenzodioxoles with high yields was carried out by condensation of adamantyl‐containing ketones (adamantanone, kemantan, diamantanone) with diols, 1,2‐ethanedithiol and 2‐mercaptoethanol, 1,2‐diaminoethane and 2‐aminoethanol under the action of copper‐containing catalysts. In the case of multigram‐scale reaction of adamant‐2‐one with 1,2‐propanediol, the amount of catalyst can be reduced to 0.1 mol %.
{"title":"Synthesis of N‐,O‐,S‐Heterocyclic Spiroadamantanes by Condensation of Ketones with Bifunctional OH‐, NH‐, SH‐Acids under the Action of Copper‐Containing Catalysts","authors":"Leysan I. Gallyamova , Alfiya R. Bayguzina , Ilfir R. Ramazanov","doi":"10.1002/ajoc.202400276","DOIUrl":"10.1002/ajoc.202400276","url":null,"abstract":"<div><div>Synthesis of adamantyl‐containing cyclic ketals, spirooxazolidines, spiroimidazolidines, spirooxathiolanes, spirodithiolanes, spirooxazines, spirobenzodioxoles with high yields was carried out by condensation of adamantyl‐containing ketones (adamantanone, kemantan, diamantanone) with diols, 1,2‐ethanedithiol and 2‐mercaptoethanol, 1,2‐diaminoethane and 2‐aminoethanol under the action of copper‐containing catalysts. In the case of multigram‐scale reaction of adamant‐2‐one with 1,2‐propanediol, the amount of catalyst can be reduced to 0.1 mol %.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400276"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622345","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Prof. Dr. Tsuyoshi Murata , Satsuki Doi , Rina Ishikawa , Prof. Dr. Ko Furukawa , Prof. Dr. Yasushi Morita
We report the synthesis of a benz‐annulated derivative of trioxotriangulene (TOT), a fused polycyclic organic neutral radical, and also the investigation on the electronic effects of π‐expansion. The neutral radical species was highly stable under air in both solution and solid states. Quantum chemical calculation suggested that the molecule has a completely planar molecular structure, and the electronic spin is widely delocalized throughout the π‐skeleton while maintaining three‐fold symmetry, which was experimentally supported by electronic spin resonance spectrum. The neutral radical also showed a strong π‐association ability comparable to that of TOT neutral radical derivatives.
{"title":"π‐Expansion on a Polycyclic Stable Neutral Radical: Synthesis and Physical Properties of a Benz‐Annulated Trioxotriangulene","authors":"Prof. Dr. Tsuyoshi Murata , Satsuki Doi , Rina Ishikawa , Prof. Dr. Ko Furukawa , Prof. Dr. Yasushi Morita","doi":"10.1002/ajoc.202400690","DOIUrl":"10.1002/ajoc.202400690","url":null,"abstract":"<div><div>We report the synthesis of a benz‐annulated derivative of trioxotriangulene (<strong>TOT</strong>), a fused polycyclic organic neutral radical, and also the investigation on the electronic effects of π‐expansion. The neutral radical species was highly stable under air in both solution and solid states. Quantum chemical calculation suggested that the molecule has a completely planar molecular structure, and the electronic spin is widely delocalized throughout the π‐skeleton while maintaining three‐fold symmetry, which was experimentally supported by electronic spin resonance spectrum. The neutral radical also showed a strong π‐association ability comparable to that of <strong>TOT</strong> neutral radical derivatives.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400690"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622610","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Recent advancements in photocatalytic strategies have expanded the range of alkylating agents, including alkyl carboxylic acids and saturated hydrocarbons. Notably, alcohols are preferred for their availability, stability, and safety compared to traditional alkylating reagents such as alkyl halides. This review summarizes recent developments in photocatalytic deoxygenative alkylation using alcohols, specifically through the formation of xanthates or thionocarbonates.
{"title":"Photocatalytic Deoxygenative Alkylation with Alcohols via Xanthates or Thionocarbonates","authors":"Wei Luo , Zhong Chen , Prof. Dr. Bing Yu","doi":"10.1002/ajoc.202400627","DOIUrl":"10.1002/ajoc.202400627","url":null,"abstract":"<div><div>Recent advancements in photocatalytic strategies have expanded the range of alkylating agents, including alkyl carboxylic acids and saturated hydrocarbons. Notably, alcohols are preferred for their availability, stability, and safety compared to traditional alkylating reagents such as alkyl halides. This review summarizes recent developments in photocatalytic deoxygenative alkylation using alcohols, specifically through the formation of xanthates or thionocarbonates.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400627"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
An enantioselective protocol for the synthesis of 2‐hydroxymethylaziridines with a tetrasubstituted carbon stereocenter have been established through the copper‐catalyzed asymmetric desymmetrization of 2‐substituted 2‐amino‐1,3‐diol derivatives by monosulfonylation. The present transformation consists of a reaction sequence involving the enantioselective monosulfonylation of 2‐amino‐1,3‐diols and the intramolecular ring closure of the resultant monosulfonylated products, which provides an efficient and straightforward entry to optically active 2‐substituted 2‐hydroxymethylaziridines. The potential synthetic utility of the present reaction is exemplified by the derivatization of the obtained aziridines into a variety of nitrogen‐containing molecules such as amino alcohols and functionalized aziridine derivatives with high enantiopurities.
{"title":"Enantioselective Synthesis of 2‐Substituted 2‐Hydroxymethylaziridines by Copper‐Catalyzed Sulfonylative Desymmetrization of 2‐Amino‐1,3‐Diols","authors":"Kosuke Yamamoto , Eibu Sakata , Anri Uehara , Masami Kuriyama , Osamu Onomura","doi":"10.1002/ajoc.202400643","DOIUrl":"10.1002/ajoc.202400643","url":null,"abstract":"<div><div>An enantioselective protocol for the synthesis of 2‐hydroxymethylaziridines with a tetrasubstituted carbon stereocenter have been established through the copper‐catalyzed asymmetric desymmetrization of 2‐substituted 2‐amino‐1,3‐diol derivatives by monosulfonylation. The present transformation consists of a reaction sequence involving the enantioselective monosulfonylation of 2‐amino‐1,3‐diols and the intramolecular ring closure of the resultant monosulfonylated products, which provides an efficient and straightforward entry to optically active 2‐substituted 2‐hydroxymethylaziridines. The potential synthetic utility of the present reaction is exemplified by the derivatization of the obtained aziridines into a variety of nitrogen‐containing molecules such as amino alcohols and functionalized aziridine derivatives with high enantiopurities.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400643"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622723","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yuito Takatsuji , Prof. Dr. Yoshinosuke Usuki , Prof. Dr. Tetsuya Satoh
The rhodium(III)‐catalyzed arylation of dimethyl itaconate with arylboronic acids proceeds smoothly under mild conditions to produce benzylidenesuccinates. The present reaction provides a simple synthesis route to benzylidenesuccinates, which are of interest due to their biological activities, from readily available substrates.
{"title":"Rhodium(III)‐Catalyzed Arylation of Dimethyl Itaconate: Facile Access to Substituted Benzylidenesuccinates","authors":"Yuito Takatsuji , Prof. Dr. Yoshinosuke Usuki , Prof. Dr. Tetsuya Satoh","doi":"10.1002/ajoc.202400589","DOIUrl":"10.1002/ajoc.202400589","url":null,"abstract":"<div><div>The rhodium(III)‐catalyzed arylation of dimethyl itaconate with arylboronic acids proceeds smoothly under mild conditions to produce benzylidenesuccinates. The present reaction provides a simple synthesis route to benzylidenesuccinates, which are of interest due to their biological activities, from readily available substrates.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400589"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622340","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Nikhil Sodhi , Manish Kumar , Manisha Yadav , Rajni Kadian , Sena Atici , Dr. Jose Pedro Friedmann Angeli , Dr. Vijay P. Singh
In search for better synthetic antioxidants, aminic organoselenides carrying amine and benzamide groups at ortho‐positions to the selenium atom were synthesized from alkyl halides and in situ generated sodiumselenolates as nucleophile by the sodium borohydride reduction of corresponding diselenides. The single crystal X‐ray structure of one compound showed the weak intramolecular Se⋅⋅⋅H interactions with free amine group. The presence of Se⋅⋅⋅H interactions was further confirmed using natural bond orbital (NBO) and atoms in molecules (AIM) calculations, respectively. The glutathione peroxidase enzyme (GPx)‐like antioxidant activity of all compounds was evaluated using thiophenol assay. The best antioxidant exhibited nearly 5 and 10 times greater activities than Oct2Se2 and Ph2Se2 used as references, respectively. The most active catalysts carrying a strong electron‐donating group were further investigated at different concentrations of thiol for determining the catalytic parameters. These GPx mimics have shown anti‐ferroptotic activity in a 4‐OH‐tamoxifen (TAM) inducible GPx4 knockout cell line and protected cells from cell death induced by loss of GPx4 enzyme. In silico molecular docking studies showed that all antioxidants demonstrated promising Moldock scores with human 15‐lipoxygenase‐2 enzyme.
{"title":"Glutathione Peroxidase‐Mimics Organoselenium Amines: Anti‐Ferroptotic Properties and an In Silico Study of 15‐Lipoxygenase‐2","authors":"Nikhil Sodhi , Manish Kumar , Manisha Yadav , Rajni Kadian , Sena Atici , Dr. Jose Pedro Friedmann Angeli , Dr. Vijay P. Singh","doi":"10.1002/ajoc.202400606","DOIUrl":"10.1002/ajoc.202400606","url":null,"abstract":"<div><div>In search for better synthetic antioxidants, aminic organoselenides carrying amine and benzamide groups at <em>ortho</em>‐positions to the selenium atom were synthesized from alkyl halides and <em>in situ</em> generated sodiumselenolates as nucleophile by the sodium borohydride reduction of corresponding diselenides. The single crystal X‐ray structure of one compound showed the weak intramolecular Se⋅⋅⋅H interactions with free amine group. The presence of Se⋅⋅⋅H interactions was further confirmed using natural bond orbital (NBO) and atoms in molecules (AIM) calculations, respectively. The glutathione peroxidase enzyme (GPx)‐like antioxidant activity of all compounds was evaluated using thiophenol assay. The best antioxidant exhibited nearly 5 and 10 times greater activities than Oct<sub>2</sub>Se<sub>2</sub> and Ph<sub>2</sub>Se<sub>2</sub> used as references, respectively. The most active catalysts carrying a strong electron‐donating group were further investigated at different concentrations of thiol for determining the catalytic parameters. These GPx mimics have shown anti‐ferroptotic activity in a 4‐OH‐tamoxifen (TAM) inducible GPx4 knockout cell line and protected cells from cell death induced by loss of GPx4 enzyme. <em>In silico</em> molecular docking studies showed that all antioxidants demonstrated promising Moldock scores with human 15‐lipoxygenase‐2 enzyme.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400606"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622344","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dr. Kuan‐Hsun Huang , Yao‐Ping Lo , Dr. Anupam Mukherjee , Dr. Badugu Devendar , Sandeep Sharma , I.‐Chen Chiu , Yu‐Pei Chang , Yi‐Chuan Chang , Prof. Chi‐Phi Wu , Prof. Chun‐Chen Liao , Prof. Gary Jing Chuang
The Corey–Chaykovsky cyclopropanation of readily available masked o‐benzoquinones (MOBs) has been investigated to generate functionalized bicyclo[4.1.0]heptane derivatives with regioselectivity. The resulting bicyclic products were subjected to a sequence of hydrolysis, BF₃ ⋅ Et₂O‐mediated ring‐opening, and then again hydrolysis to access various tropolone derivatives – a class of molecules with significant roles in synthetic, biological, and theoretical chemistry. Utilizing an improved approach based on established cyclopropanation and ring‐opening strategies, several bicyclo[4.1.0]heptanes, tropolone difluorides, and tropolones can be synthesized from readily available MOBs. Our efforts focused on modifying each step to make these reactions general and of considerable practical value.
{"title":"A Practical Approach to Cyclopropanation of Masked o‐Benzoquinones with Applications in Tropolone Derivative Synthesis","authors":"Dr. Kuan‐Hsun Huang , Yao‐Ping Lo , Dr. Anupam Mukherjee , Dr. Badugu Devendar , Sandeep Sharma , I.‐Chen Chiu , Yu‐Pei Chang , Yi‐Chuan Chang , Prof. Chi‐Phi Wu , Prof. Chun‐Chen Liao , Prof. Gary Jing Chuang","doi":"10.1002/ajoc.202400659","DOIUrl":"10.1002/ajoc.202400659","url":null,"abstract":"<div><div>The Corey–Chaykovsky cyclopropanation of readily available masked <em>o</em>‐benzoquinones (MOBs) has been investigated to generate functionalized bicyclo[4.1.0]heptane derivatives with regioselectivity. The resulting bicyclic products were subjected to a sequence of hydrolysis, BF₃ ⋅ Et₂O‐mediated ring‐opening, and then again hydrolysis to access various tropolone derivatives – a class of molecules with significant roles in synthetic, biological, and theoretical chemistry. Utilizing an improved approach based on established cyclopropanation and ring‐opening strategies, several bicyclo[4.1.0]heptanes, tropolone difluorides, and tropolones can be synthesized from readily available MOBs. Our efforts focused on modifying each step to make these reactions general and of considerable practical value.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400659"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622346","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Cuili Chen , Shan Lu , Yanmin Zou , Di Mao , Hideaki Kakeya
Endophytes have been recognized as important sources for discovering novel bioactive natural products with diverse structures and biological activities. This review focuses on the endophytes of Tripterygium wilfordii Hook. f. (T. wilfordii), a famous traditional medicinal plant, and summarizes the producing microbes, chemical diversities, and bioactivities of the metabolites discovered from the T. wilfordii ‐associated endophytes over the past thirty years (1995–2024). One hundred and one metabolites together with their bioactivities from twelve endophytes are systematically reviewed. A comprehensive comparison of the 101 metabolites with those isolated from T. wilfordii reveals that the T. wilfordii‐associated endophytes produce structurally distinct metabolites with diverse biological activities. To the best of our knowledge, this is the first holistic overview of the T. wilfordii‐associated endophytes and their secondary metabolites.
{"title":"Secondary Metabolites from Tripterygium wilfordii Hook. f.‐Associated Endophytes: Producing Microbes, Structures, and Bioactivities","authors":"Cuili Chen , Shan Lu , Yanmin Zou , Di Mao , Hideaki Kakeya","doi":"10.1002/ajoc.202400696","DOIUrl":"10.1002/ajoc.202400696","url":null,"abstract":"<div><div>Endophytes have been recognized as important sources for discovering novel bioactive natural products with diverse structures and biological activities. This review focuses on the endophytes of <em>Tripterygium wilfordii</em> Hook. f. (<em>T. wilfordii</em>), a famous traditional medicinal plant, and summarizes the producing microbes, chemical diversities, and bioactivities of the metabolites discovered from the <em>T. wilfordii</em> ‐associated endophytes over the past thirty years (1995–2024). One hundred and one metabolites together with their bioactivities from twelve endophytes are systematically reviewed. A comprehensive comparison of the 101 metabolites with those isolated from <em>T. wilfordii</em> reveals that the <em>T. wilfordii</em>‐associated endophytes produce structurally distinct metabolites with diverse biological activities. To the best of our knowledge, this is the first holistic overview of the <em>T. wilfordii</em>‐associated endophytes and their secondary metabolites.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400696"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622387","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Liang Ye , Haibin Xu , Jiong Yu , Han Yan , Min Wang , Pinhua Li
A convenient and efficient protocol for the synthesis of 3,3‐dialkylated oxindoles through photocatalytic aerobic radical‐cascade alkylation/cyclization of N‐arylacrylamides with the alkyl radicals generated from simple alkanes is described. This method features a broad substrate scope, inexpensive alkyl radical precursors, simple conditions and good yields.
{"title":"Photocatalytic Cascade Alkylation/Cyclization of N‐Arylacrylamides with Simple Alkanes: A Convenient Approach to Quaternary C3 Alkylated Oxindoles","authors":"Liang Ye , Haibin Xu , Jiong Yu , Han Yan , Min Wang , Pinhua Li","doi":"10.1002/ajoc.202400554","DOIUrl":"10.1002/ajoc.202400554","url":null,"abstract":"<div><div>A convenient and efficient protocol for the synthesis of 3,3‐dialkylated oxindoles through photocatalytic aerobic radical‐cascade alkylation/cyclization of <em>N</em>‐arylacrylamides with the alkyl radicals generated from simple alkanes is described. This method features a broad substrate scope, inexpensive alkyl radical precursors, simple conditions and good yields.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400554"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622550","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Wenjun Liu , Xinghui Jin , Fang Yuan , Yuexia Wang , Jianhua Zhou , Qiong Wu
A series of high energy density compounds are designed by altering the triazole, tetrazine, oxadiazole rings and energetic groups (such as −CN, −N3, −NH2, −NHNH2, −NO2, −NHNO2, −C(NO2)3, −CH(NO2)2) into 2,4,5‐trinitro‐imidazole skeleton. Their structures are optimized by density functional theory (DFT) methods at B3LYP/6‐311G (d,p) method. Based on the optimized structures, the impact of different rings and energetic groups on their energy gaps, heats of formation, detonation performance and sensitivities are investigated. The results show that compound F4 possesses the highest values of heats of formation due to their high nitrogen content. However, compound F2 possesses the highest values of detonation pressure and detonation velocity which indicates that the detonation performance are determined by values of density rather than those of heats of formation. Taking both detonation performance and impact sensitivities into consideration, compounds B4, C4, F4, I4, J4 and J8 are screened as high energy density compounds due to their excellent detonation performance and acceptable sensitivities compared to those of RDX. Finally, the distribution of frontier molecular orbital, the electrostatic potential area distribution, thermodynamic properties and weak interactions of the screened compounds are fully investigated.
{"title":"A Promising Strategy for Searching High Energy Density Materials Based on 2,4,5‐Trinitro‐Imidazole Functional Backbone","authors":"Wenjun Liu , Xinghui Jin , Fang Yuan , Yuexia Wang , Jianhua Zhou , Qiong Wu","doi":"10.1002/ajoc.202400719","DOIUrl":"10.1002/ajoc.202400719","url":null,"abstract":"<div><div>A series of high energy density compounds are designed by altering the triazole, tetrazine, oxadiazole rings and energetic groups (such as −CN, −N<sub>3</sub>, −NH<sub>2</sub>, −NHNH<sub>2</sub>, −NO<sub>2</sub>, −NHNO<sub>2</sub>, −C(NO<sub>2</sub>)<sub>3</sub>, −CH(NO<sub>2</sub>)<sub>2</sub>) into 2,4,5‐trinitro‐imidazole skeleton. Their structures are optimized by density functional theory (DFT) methods at B3LYP/6‐311G (d,p) method. Based on the optimized structures, the impact of different rings and energetic groups on their energy gaps, heats of formation, detonation performance and sensitivities are investigated. The results show that compound F4 possesses the highest values of heats of formation due to their high nitrogen content. However, compound F2 possesses the highest values of detonation pressure and detonation velocity which indicates that the detonation performance are determined by values of density rather than those of heats of formation. Taking both detonation performance and impact sensitivities into consideration, compounds B4, C4, F4, I4, J4 and J8 are screened as high energy density compounds due to their excellent detonation performance and acceptable sensitivities compared to those of RDX. Finally, the distribution of frontier molecular orbital, the electrostatic potential area distribution, thermodynamic properties and weak interactions of the screened compounds are fully investigated.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400719"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622281","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
扫码关注我们
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号