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Study On The Interaction And Properties Of Alkylsulfonium Salt With Common

Posted on:2016-09-20Degree:MasterType:Thesis
Country:ChinaCandidate:J L YuFull Text:PDF
GTID:2271330479955277Subject:Analytical Chemistry
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Cucurbit[n]urils is a family of molecular container hosts bearing a rigid hydrophobic cavity and two identical carbonyl fringed portals. They have attracted much attention in supramolecular chemistry such as host-guest chemistry,coordination chemistry, molecular recognition and self-assembly due to their superior molecular recognition properties in aqueous media.As an organic synthetic intermediate, Sulfonium salt can undertake nucleophilic substitution reaction, sulfur, ylide and elimination reaction.Especially in alkaline conditions, with a lack of electronic carbon carbon double bond, aldehydes, ketones,imines reaction synthesis of organic compounds on three and ternary compound is to build natural products and bioactive pesticide reagent common modules.In medicinal chemistry, sulfonium salt can not only for synthesis of bioactive molecules, but also can efficiently synthesized with optical activity of drug molecules, improve drug molecule biological activity. Lithium ions can increase the proportion of cis reaction of epoxy propane, so as to regulate the complementation of epoxy propane reactionselectivity. so the cucurbit[n]urils and sulfonium salt supramolecular system has a certain social and economic significance.On the basis of existing research literature reports and laboratory, introducing the preparation of sulfioum and the sulfonium is chosen as guest, Q[7],Q[8] and guest based on 1HMNR spectroscopy,uv-visible absorption spectrum,isothermal titer thermal technology,thermogravimetric and infrared technology are detected of their each interaction. The result is:the sulfonium access Q[7] and form inclusion compiex of 1:1 and the stability of sulfonium is stronger than before;the sulfonium access Q[8] and form inclusion compiex of 2:1.Antiviral drugs-amantadine and Q[7~8] are form stable and mole ratio is1:1.Plant growth regulator-3-indolebutyric acid(IBA) have been formed with Q[8]and mole ratio is 1:1.In a certain p H range, the cucuibit[n]uils(Q[7~8]) can increase the stability of DMBS and DMNS,and also regulate the concentration of sulfur ylide reagent.By thermal analysis, when the Q[7] and aryl sulfonium salt form inclusion compiex, the more stable of the Q[7] and increased the aryl sulfonium salts on the stability of carbon- sulfur bond. When add the amantadine to the mixed aqua of the sulfonium and cucuibit[n]uils(Q[7-8]),the sulfonium was pushed by amantadine,and form inclusion compiex,the amantadine with cucuibit[n]uils more easier to form than sulfonium with cucuibit[n]uils,which serious interference cucuibit[n]uils regulate and control the concentration of sulfur ylide reagent.When add the sulfonium to the mixed solution of the IBA and Q[8],chemical shift of 1HMNR spectroscopy are to high field mobile,and IBA with sulfonium are enter into cucuibit[n]uils,to form a cooperative mode.So, Q[7]package and aryl sulfonium salt, cucuibit[n]uils can increase the stability of the aromatic sulfonium salt,it can increase the proportion of cis. Substance with cucuibit[n]uils can form inclusion compiex, can reduce the stability of aryl sulfonium salt and cucuibit[n]uils inclusion compiex, and may be conducive to increase the proportion of cis. Therefore aryl sulfonium salt and supramolecular interactionresearch, to study the inclusion compiex and the metal ions coordinated control provides the basis theory for cis trans selectivity, to explore the application prospects of cucuibit[n]uils in medicinal chemistry.
Keywords/Search Tags:cucurbiturils, sulfonium, amantadine, IBA, 1HNMR techniques, UV-vis absorption spectroscopy, isothermal titration calorimetry
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