Alkyltriphenylphosphonium Arenesulfonates: Synthesis and Structures

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Accounts of Chemical Research Pub Date : 2024-05-16 DOI:10.1134/S107032842360136X

V. V. Sharutin, O. K. Sharutina, E. S. Mekhanoshina

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Abstract

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−C_Ar (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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烷基三苯基鏻丙烯磺酸盐：合成与结构

[Ph3PCH2СN][OSO2C6H4(COOH)-2]（II）、[Ph3PCH2C(O)Me]-[OSO2С6H4(COOH-2]（III）和[Ph3PCH2C(O)Me][OSO2Naft-1]（IV）。根据 X 射线衍射 (XRD) 数据，化合物 I-IV 的晶体具有离子结构，其中含有四面体烷基三苯基膦阳离子（P-С 1.7820(19)-1.8330(20) Å，CPC 105.37(10)°-112.09(12)°）和异烷基磺酸阴离子。化合物 I 的晶体中含有氢键（S=O--H-OC(O) 1.87 Å），将异磺酸阴离子连接成链。化合物 I-IV 晶体的结构组织主要是由阳离子和阴离子之间的许多弱氢键形成的，例如 S=O---H-CAr (2.29-2.70 Å)、C=O∙∙H-C (2.48 和 2.59 Å) 以及 N∙∙∙H-C (2.62-2.68 Å)。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： 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. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.