Linear oligosulfoxides: Synthesis and solubility studies |
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| Affiliation: | 1. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA;2. Nalco Champion, an Ecolab Company, 11177 South Stadium Drive, Sugar Land, TX 77478, USA;1. V. I. Vernadsky Crimean Federal University, Simferopol 295007, Russia;2. B. I. Verkin Institute for Low Temperature Physics and Engineering of the NASU, Kharkov 61103, Ukraine;3. Russian Quantum Center, Skolkovo, Moscow 143025, Russia;4. Lomonosov Moscow State University, Moscow 119991, Russia;1. School of Earth and Environmental Sciences and Williamson Research Centre for Molecular Environmental Science, The University of Manchester, Manchester, M13 9PL, UK;2. ETH Zürich, Inst. F. Biogeochemie u. Schadstoffdynamik, CHN G48 Universitätstrasse 16, 8092 Zürich, Switzerland;1. Department of Physics, School of Sciences, Lovely Professional University, Punjab 144411 India;2. Sankofa Advisors, 7/604 Garden Enclave, Vasant Viharn Thane 400610 India;3. Nanosructures Engineering and Modeling Laboratory, Department of Metallurgical Engineering and Materials Science, IIT Bombay, Powai, Mumbai 40076 India |
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| Abstract: | Synthesis of three linear oligosulfoxides containing up to six sulfoxide groups was achieved by multiple SN2 reactions between an alkanethiol and alkyl tosylate to give a linear oligosulfide followed by oxidation of the oligosulfide with sodium periodate to give an oligosulfoxide. The challenge of complete avoidance of partial oxidation and over oxidation was easily overcome using the sodium periodate oxidation conditions. Although sulfoxide is a highly polar functional group, the oligosulfoxides were found to have limited solubility in many solvents including DMSO and water, which disobeys the “like dissolves like” rule. The surprising solubility pattern of oligosulfoxides was discussed in the context of the drastically different solubility patterns of polyethylene glycol (PEG), poly(butylene oxide), and poly(methylene oxide). According to a dissolution model, solubility properties of linear oligomers including the oligosulfoxides and PEGs may be heavily affected by their conformations and the suitability of their conformations in water for maximizing attractive interactions between them and water. Based on these hypotheses, the limited solubility of the present oligosulfoxides may not imply the low solubility of similar molecules. |
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| Keywords: | Dissolution model Oligosulfoxide Polyethylene glycol Synthesis |
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