Alkyltriphenylphosphonium Arenesulfonates: Synthesis and Structures

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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) A, CPC 05.37(10)°−112.09(12)°) and arenesulfonate anions. The crystal of compound I contains hydrogen bonds (S=O∙∙∙H−OC(O) 1.87 A) 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 A), C=O∙∙∙H–C (2.48 and 2.59 A), and N∙∙∙H–C (2.62−2.68 A).

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V. V. Sharutin

South Ural State University (National Research University)

Author for correspondence.
Email: sharutin50@mail.ru
Russian Federation, Chelyabinsk

O. K. Sharutina

South Ural State University (National Research University)

Email: sharutin50@mail.ru
Russian Federation, Chelyabinsk

E. S. Mekhanoshina

South Ural State University (National Research University)

Email: sharutin50@mail.ru
Russian Federation, Chelyabinsk

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2. Fig. 1. General view of connection I. Bond lengths: P—C — 1.790(2)-1.820(3); S—O — 1.443(3)-1.464(2); S—C — 1.783(2) Å and valence angles: CPC — 105.37(10)-112.09(12)°.

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3. Fig. 2. General view of the connection II. Bond lengths: P—C — 1.785(2)-1.833(2); S—O — 1.446(2)-1.464(2); S—C — 1.794(2) Å and valence angles: CPC — 108.31(11)-112.09(10)°.

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4. Fig. 3. General view of the connection III. Bond lengths: P—C — 1.784(5)-1.795(5); S—O — 1.433(4)-1.457(5); S—C — 1.786(5) Å and valence angles: CPC — 107.1(3)-112.6(3)°.

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5. Fig. 4. General view of the connection IV. Bond lengths: P—C — 1.782(2)-1.796(2); S—O — 1.433(2)-1.440(2) Å; S—C — 1.776(2) Å and valence angles: CPC — 105.23(9)-112.20(9)°.

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6. Fig. 5. The chain of arenesulfonate anions in crystal I.

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