3,5-Dimethylpyrazole promoted sulfonation of acetic anhydride by H₂SO₄ to sulfoacetic acid and methanedisulfonic acid, and crystal structures of the complexes with Co²⁺, Zn²⁺, Ba²⁺, Pb²⁺ an

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• 作者：Sarut Jianrattanasawat ; Gellert Mezei ; ^{gellert.mezei@wmich.edu}
• 关键词：3 ; 5-Dimethylpyrazole-4-sulfonic acid ; Sulfoacetic acid ; Methanedisulfonic acid ; Nuclear magnetic resonance (NMR) spectroscopy ; X-ray crystal structures ; Coordination polymers
• 刊名：Inorganica Chimica Acta
• 出版年：2012
• 期刊代码：40_00201693
• 类别：ch
• 出版时间：1 April, 2012
• 卷：384
• 期：Complete
• 页码：318-323
• 文件大小：1204 K

摘要

Sulfuric acid can sulfonate acetic anhydride (but not acetic acid) to sulfoacetic acid, and also to methanedisulfonic acid in the presence of 3,5-dimethylpyrazole. Under the experimental conditions employed, sulfonation of 3,5-dimethylpyrazole with concentrated sulfuric acid in acetic anhydride/acetic acid as solvent leads to a mixture of approximately 47 mol%3,5-dimethylpyrazole-4-sulfonic acid, 34 mol%sulfoacetic acid and 19 mol%methanedisulfonic acid, as determined by ¹H NMR spectroscopy. The Co²⁺, Zn²⁺, Ba²⁺ and Pb²⁺ complexes of the sulfoacetate ligand, as well as the Cs⁺ complex of the methanedisulfonate ligand were isolated upon crystallization of the compounds obtained from the reaction of the above ligand mixture with the corresponding metal oxide or carbonate in water. Single-crystal X-ray crystallography of Co(O₃SCH₂CO₂)(H₂O)₃, Zn(O₃SCH₂CO₂)(H₂O)₃, Ba(O₃SCH₂CO₂)(H₂O), Pb(O₃SCH₂CO₂)(H₂O) and Cs₂(O₃SCH₂SO₃) reveals a variety of new coordination modes of the two sulfonated ligands within those structures.