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Open AccessArticle

Synthesis and Crystallographic Characterization of X-Substituted 2,4-Dinitrophenyl-4′-phenylbenzenesulfonates

1
Department of Chemistry, Grand Valley State University, 1 Campus Drive., Allendale, MI 49401, USA
2
Center for Crystallographic Research, Department of Chemistry, Michigan State University, 578 S. Shaw Lane, East Lansing, MI 48824, USA
*
Author to whom correspondence should be addressed.
Dedicated to Dr. Howard Flack (1943–2017).
Chemistry 2020, 2(2), 591-599; https://doi.org/10.3390/chemistry2020036
Received: 9 May 2020 / Revised: 21 May 2020 / Accepted: 21 May 2020 / Published: 15 June 2020
Treatment of 2,4-dinitrophenol with sulfonyl chlorides in the presence of pyridine results in the formation of undesired pyridinium salts. In non-aqueous environments, the formation of the insoluble pyridinium salt greatly affects the formation of the desired product. A facile method of producing the desired sulfonate involves the use of an aqueous base with a water-miscible solvent. Herein, we present the optimization of methods for the formation of sulfonates and its application in the production of desired x-substituted 2,4-dinitrophenyl-4′-phenylbenzenesulfonates. This strategy is environmentally benign and supports a wide range of starting materials. Additionally, the intermolecular interactions of these sulfonate compounds were investigated using single-crystal x-ray diffraction data. View Full-Text
Keywords: arylsulfonates; pyridinium salt formation; single-phase solvent system; sulfonate synthesis; sulfonyl chlorides; X-ray crystallography arylsulfonates; pyridinium salt formation; single-phase solvent system; sulfonate synthesis; sulfonyl chlorides; X-ray crystallography
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    Doi: 10.5281/zenodo.3818464
    Description: Synthesis and Crystallographic Characterization of X-Substituted 2,4-Dinitrophenyl-4’-phenylbenzenesulfonates
MDPI and ACS Style

Stenfors, B.A.; Staples, R.J.; Biros, S.M.; Ngassa, F.N. Synthesis and Crystallographic Characterization of X-Substituted 2,4-Dinitrophenyl-4′-phenylbenzenesulfonates. Chemistry 2020, 2, 591-599.

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