In the context of a scientific program aiming at discovering new hypotensive agents through the original combination of natural product discovery and superacid chemistry diversification, and. Request pdf superacid chemistry, second edition the chemistry of superacids has developed in the last two decades into a field of growing interest and importance. Commercially available superacids include trifluoromethanesulfonic acid cf. This is exactly what is happening in magic acid, forming weakly or noncoordinating anions as conjugated base. Magic acid and superacid chemistry across conventional lines. Superacid chemistry on mildly acidic water the journal.
This paper describes the superacidcatalyzed chemistry of olefinic amines and related compounds. Acidity is indicated by the hammett acidity function, h 0 like ph, h 0 is a measure of acidity. Free download methods and reagents for green chemistry. T he term superacid was first proposed in 1923 by conant to describe acid systems stronger than conventional mineral acids 11. Request pdf superacid chemistry, second edition the chemistry of superacids has developed in the last two decades into a field of growing interest and. A superacid is a system more acidic than 100% sulfuric acid with h0 values lower than.
It has been found 1012 that solgel chemistry offers a high degree of homogeneity of the. According to the modern definition, a superacid is a medium in which the chemical potential of. Hino, m, arata, k 1980 synthesis of solid superacid catalyst with acid strength of h016. Gases, liquids and solids, gas laws, general gas equations.
Bioactive natural product and superacid chemistry for lead. The chemistry of superacids deals with acid systems stronger than conventional strong mineral bronsted acids such as sulfuric acid and lewis acids such as aluminum trichloride. Download fulltext pdf superacidinduced reactions of nefopam article pdf available in organic chemistry international 201010 april 2010 with 28 reads. According to the classical definition, a superacid is an acid with an acidity greater than that of 100% pure sulfuric acid, which has a hammett acidity function h0 of. Perfluoroalkanesulfonic acidboron perfluoroalkanesulfonates. Carborane acids hcxb 11 y 5 z 6 x, y, z h, alk, f, cl, br, cf 3 are a class of superacids, some of which are estimated to be at least one million times stronger than 100% sulfuric acid in terms of their hammett acidity function values h 0. Antimony pentafluoride is a very dangerous substance.
Free chemistry books download free chemistry ebooks online. Calculated compounds have outstanding electron affinity and deprotonation energy, respectively. International center for materials nanoarchitectonics, world premier international wpi research initiative, national institute for materials science, tsukuba, ibaraki 305. Superacid chemistry, second edition request pdf researchgate. Pdf prospects of using solid superacids as catalysts in. The h 2 b 12 x 12 superacids can protonate benzene at room temperature a key test of superacidity that not even triflic trifluoromethanesulfonic acid can achieve. A comprehensive and rational evaluation of this reaction has led to the establishment of an. Presented herein is the development of quantitative reactivity and bond strength scales by using mass spectrometry ms. Dodoneine ddn is one of the active compounds identified from agelanthus dodoneifolius, which is a medicinal plant used in african pharmacopeia and traditional medicine for the treatment of hypertension. For comparison purposes, diphenylmethanol 10 was also reacted with benzene and triflic acid scheme 3. An equimolar mixture of hso 3 f and sbf 5 is known by the trade name magic acid. New superacid systems for generation of carbocations and catalysts for electrophilic transformations of. This paper discusses the synthesis of a glycerol ketal compound obtained from condensation reaction of cyclohexanone with glycerol catalyzed by a solid superacid. Green synthesis of cyclohexanone glycerol ketal catalyzed.
Functionalized mesoporous nanocages with tunable pore diameters and their application in the synthesis of coumarins pranjal kalita dr. Superacids, although first referred to as early as 1927, were only extensively studied in the last decade. Superelectrophilic activation in superacid hfsbf 5. Superacidpromoted ionization of alkanes without carbonium ion formation. Dicationic electrophiles from olefinic amines in superacid. System upgrade on feb 12th during this period, ecommerce and registration of new users may not be available for up to 12 hours. This chapter discusses the properties of superacid systems, which have acidities comparable to, or greater than that. A variety of olefinic amines are found to react with benzene in cf3so3h triflic acid to give addition products in good yields 75. The discovery that carbocations can be stabilized in super acid media, e. When diphenylmethanol is reacted with benzene and triflic acid, two products are. Bond strength and reactivity scales for lewis superacid. The stability of these structures is discussed, while some of the. Superacids are acids which have acidic strength much higher than that of 100% pure sulphuric acid.
These books are not hosted on our servers and these books are material of their respective publishersorganizations. Get your kindle here, or download a free kindle reading app. Cyclodimerization of ethylene oxide eo to 1,4dioxane don by using superacids and their derivatives as catalysts was examined. The first edition of superacid chemistry, published in 1985, quickly became the definitive work in the field. Atomic theory and nature of atoms, introduction to the periodic table.
Polymerization experiments with isobutylene and styrene carried out at high acid concentrations and in the virtual absence of nucleophile, i. We reasoned that diphenylmethanol should ionize cleanly to the monocationic carbocation in superacid and its chemistry would provide a good comparison with the nefopamderived dicationic intermediate i. Carboranes were recently shown to be superacids and have the added. According to the modern definition, a superacid is a medium in which the chemical potential of the proton is higher than in pure sulfuric acid. Much later, olah popularized the term in the study of stable carbocations in highly acidic media 22. Like ph, h 0 is a logarithmic scale 100% sulfuric acid has an h 0 of 12. This means fluoroantimonic acid is 10 19 more acidic than pure sulfuric acid.
Superacids are defined as being stronger acids than pure sulfuric acid, and can be used to stabilize otherwise reactive cations. Superacid chemistry wiley online books wiley online library. Canadian journal of chemistry canadian science publishing. Pdf solid supracids are employed as catalysts for many reactions. Results are discussed on the basis of the catalyst nature. A general mechanism is proposed that invokes the formation of reactive, dicationic electrophiles. Superacidcatalyzed friedelcrafts polyhydroxyalkylation. Expanding molecular diversity in nitrogencontaining compounds series by fluorination.
The structure of the atom, the organization of the elements, describing compounds, problem solving and the mole, mixtures and their properties, chemical reactions, acids and bases, energy of chemical changes and nuclear changes. The extremely low nucleophilicity of the counterions in superacidic systems is especially useful for the preparation of stable, electrondeficient cations, particularly carbocations. In superacids, the chemical potential of protons is much higher. The chemistry of superacids has developed in the last two decades into a field of growing interest and importance. A systematic screening of catalysts is often necessary when developing synthetic methodologies.
Acidities up to 1012 times that of sulfuric acid have now been obtained. According to gillespies arbitrary but now widely accepted definition, a superacid is an acid system stronger than 100% sulfuric acid 33. Free download methods and reagents for green chemistry an introduction edited by pietro tundo, alvise perosa and fulvio zecchini, published by john wiley and sons inc. According to the classical definition, a superacid is an acid with an acidity greater than that of 100% pure sulfuric acid, which has a hammett acidity function h 0 of. Superacid chemistry, 2nd edition book chemistryviews. The chemistry of superacids deals with acid systems stronger than conventional strong mineral bronsted acids such as sulfuric acid and lewis acids such as. Snntf 2 4 is an optimal catalyst to promote this challenging transformation at low loading and the reaction shows promising scope.
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