V. V. Sharutin, O. K. Sharutina, E. S. Mekhanoshina
{"title":"烷基三苯基鏻丙烯磺酸盐：合成与结构","authors":"V. V. Sharutin, O. K. Sharutina, E. S. Mekhanoshina","doi":"10.1134/S107032842360136X","DOIUrl":null,"url":null,"abstract":"<p>The reactions of equimolar amounts of alkyltriphenylphosphonium bromide with arenesulfonic acids in an aqueous-acetone solution afford alkyltriphenylphosphonium arenesulfonates [Ph<sub>3</sub>PCH<sub>2</sub>ОMe]-[OSO<sub>2</sub>C<sub>6</sub>H<sub>3</sub>(OH-4)(COOH-3)] (<b>I</b>), [Ph<sub>3</sub>PCH<sub>2</sub>СN][OSO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>(COOH)-2] (<b>II</b>), [Ph<sub>3</sub>PCH<sub>2</sub>C(O)Me]-[OSO<sub>2</sub>С<sub>6</sub>H<sub>4</sub>(COOH-2] (<b>III</b>), and [Ph<sub>3</sub>PCH<sub>2</sub>C(O)Me][OSO<sub>2</sub>Naft-1] (<b>IV</b>). According to the X-ray diffraction (XRD) data, the crystals of compounds <b>I−IV</b> have ionic structures with tetrahedral alkyltriphenylphosphonium cations (P−С 1.7820(19)−1.8330(20) Å, CPC 105.37(10)°−112.09(12)°) and arenesulfonate anions. The crystal of compound <b>I</b> contains hydrogen bonds (S=O···H−OC(O) 1.87 Å) linking the arenesulfonate anions into chains. The structural organization of the crystals of compounds <b>I</b>−<b>IV</b> is mainly formed due to numerous weak hydrogen bonds between the cations and anions, for instance, S=O···H−C<sub>Ar</sub> (2.29−2.70 Å), C=O∙∙∙H–C (2.48 and 2.59 Å), and N∙∙∙H–C (2.62−2.68 Å).</p>","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":null,"pages":null},"PeriodicalIF":16.4000,"publicationDate":"2024-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Alkyltriphenylphosphonium Arenesulfonates: Synthesis and Structures\",\"authors\":\"V. V. Sharutin, O. K. Sharutina, E. S. Mekhanoshina\",\"doi\":\"10.1134/S107032842360136X\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>The reactions of equimolar amounts of alkyltriphenylphosphonium bromide with arenesulfonic acids in an aqueous-acetone solution afford alkyltriphenylphosphonium arenesulfonates [Ph<sub>3</sub>PCH<sub>2</sub>ОMe]-[OSO<sub>2</sub>C<sub>6</sub>H<sub>3</sub>(OH-4)(COOH-3)] (<b>I</b>), [Ph<sub>3</sub>PCH<sub>2</sub>СN][OSO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>(COOH)-2] (<b>II</b>), [Ph<sub>3</sub>PCH<sub>2</sub>C(O)Me]-[OSO<sub>2</sub>С<sub>6</sub>H<sub>4</sub>(COOH-2] (<b>III</b>), and [Ph<sub>3</sub>PCH<sub>2</sub>C(O)Me][OSO<sub>2</sub>Naft-1] (<b>IV</b>). According to the X-ray diffraction (XRD) data, the crystals of compounds <b>I−IV</b> have ionic structures with tetrahedral alkyltriphenylphosphonium cations (P−С 1.7820(19)−1.8330(20) Å, CPC 105.37(10)°−112.09(12)°) and arenesulfonate anions. The crystal of compound <b>I</b> contains hydrogen bonds (S=O···H−OC(O) 1.87 Å) linking the arenesulfonate anions into chains. The structural organization of the crystals of compounds <b>I</b>−<b>IV</b> is mainly formed due to numerous weak hydrogen bonds between the cations and anions, for instance, S=O···H−C<sub>Ar</sub> (2.29−2.70 Å), C=O∙∙∙H–C (2.48 and 2.59 Å), and N∙∙∙H–C (2.62−2.68 Å).</p>\",\"PeriodicalId\":1,\"journal\":{\"name\":\"Accounts of Chemical Research\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":16.4000,\"publicationDate\":\"2024-05-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Accounts of Chemical Research\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1134/S107032842360136X\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S107032842360136X","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Alkyltriphenylphosphonium Arenesulfonates: Synthesis and Structures
The reactions of equimolar amounts of alkyltriphenylphosphonium bromide with arenesulfonic acids in an aqueous-acetone solution afford alkyltriphenylphosphonium arenesulfonates [Ph3PCH2ОMe]-[OSO2C6H3(OH-4)(COOH-3)] (I), [Ph3PCH2СN][OSO2C6H4(COOH)-2] (II), [Ph3PCH2C(O)Me]-[OSO2С6H4(COOH-2] (III), and [Ph3PCH2C(O)Me][OSO2Naft-1] (IV). According to the X-ray diffraction (XRD) data, the crystals of compounds I−IV have ionic structures with tetrahedral alkyltriphenylphosphonium cations (P−С 1.7820(19)−1.8330(20) Å, CPC 105.37(10)°−112.09(12)°) and arenesulfonate anions. The crystal of compound I contains hydrogen bonds (S=O···H−OC(O) 1.87 Å) linking the arenesulfonate anions into chains. The structural organization of the crystals of compounds I−IV is mainly formed due to numerous weak hydrogen bonds between the cations and anions, for instance, S=O···H−CAr (2.29−2.70 Å), C=O∙∙∙H–C (2.48 and 2.59 Å), and N∙∙∙H–C (2.62−2.68 Å).
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Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
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