Solvents amphoteric

Colorless Or slightly yellow, transparent brittle practically odorless, tasteless sheets, flakes, or coarse powder Swells up and absorbs 5 -10 times its weight of water to form a gel in solutions below 35 40. Sol in hot water glycerol, acetic acid. Insol in organic solvents. Amphoteric. 

Leaflets + HgO from HgO. M.p. 238 deoomp. [a] 4- 40° in Py. Sol. Py. Spar. sol. most org. solvents. Amphoteric. Gives characteristic blue Keller test of ergot alkaloids. 

The dissociation, or autoprotolysis constant for a solvent, SH, relates the concentration of the protonated solvent, SH2, to that of the deprotonated solvent, S . For amphoteric solvents, which can act as both proton donors and proton acceptors, the autoprotolysis reaction is... 

Physical and ionic adsorption may be either monolayer or multilayer (12). Capillary stmctures in which the diameters of the capillaries are small, ie, one to two molecular diameters, exhibit a marked hysteresis effect on desorption. Sorbed surfactant solutes do not necessarily cover ah. of a sohd iaterface and their presence does not preclude adsorption of solvent molecules. The strength of surfactant sorption generally foUows the order cationic > anionic > nonionic. Surfaces to which this rule apphes include metals, glass, plastics, textiles (13), paper, and many minerals. The pH is an important modifying factor in the adsorption of all ionic surfactants but especially for amphoteric surfactants which are least soluble at their isoelectric point. The speed and degree of adsorption are increased by the presence of dissolved inorganic salts in surfactant solutions (14). 

Isolation. Isolation procedures rely primarily on solubiHty, adsorption, and ionic characteristics of the P-lactam antibiotic to separate it from the large number of other components present in the fermentation mixture. The penicillins ate monobasic catboxyHc acids which lend themselves to solvent extraction techniques (154). Pencillin V, because of its improved acid stabiHty over other penicillins, can be precipitated dkecdy from broth filtrates by addition of dilute sulfuric acid (154,156). The separation process for cephalosporin C is more complex because the amphoteric nature of cephalosporin C precludes dkect extraction into organic solvents. This antibiotic is isolated through the use of a combination of ion-exchange and precipitation procedures (157). The use of neutral, macroporous resins such as XAD-2 or XAD-4, allows for a more rapid elimination of impurities in the initial steps of the isolation (158). The isolation procedure for cephamycin C also involves a series of ion exchange treatments (103). 

In general, the tetracyclines are yellow crystalline compounds that have amphoteric properties (Fig. 2) (15). They are soluble in both aqueous acid and aqueous base. The acid salts tend to be soluble in organic solvents such as 1-butanol, dioxane, and 2-ethoxyethanol In fact, 1-butanol is used to extract the salts from aqueous solution. 

Properties. Dicyandiamide (2) (cyanoguanidine [461-58-5]) is the dimer of cyanamide and crystallizes ia colorless monoclinic prisms. It is amphoteric, and generally soluble in polar solvents and insoluble in nonpolar solvents. Its properties are Hsted in Table 3. 

Amphoteric hydrophobic Blue dextran, collagen, gelatin, hydrophobic proteins Hydrophobic peptides Buffer or salt solution with organic solvent (e,g, 20% CH3CN in 0.1 M NaNOi) 35-45% CH3CN in 0.1% TFA... 

Proton donor/acceptors (amphoteric solvents) water, alcohols. 

In the simplest case the acid may be positively charged and its base uncharged, or the acid is uncharged and its base negatively charged e.g., for water as an amphoteric solvent, we have... 

Although this behavior has been illustrated starting with the metal ion, analogous equations can be written starting with the metal oxide as well as the hydroxide. Amphoteric behavior is exhibited in other solvents, as will be illustrated later. 

The amphoteric behavior of Zn2+ and Al3+ in some nonaqueous solvents has already been described. This behavior can also be demonstrated in liquid S02. For example, the aluminum compound containing the anion characteristic of the solvent forms a precipitate, which is then soluble in either the acid or base in liquid S02. This can be shown as... 

Aluminum is amphoteric, and this has been illustrated in Chapter 10 both for water as the solvent and for some nonaqueous solvents. Because of the high charge density of Al3+, solutions of aluminum salts are acidic as a result of hydrolysis. 

In this connection, water, an amphoteric solvent, can act as an acid (monoprotic, with, say, NH, as a base) ... 

The solubility of antibiotics, including CTC-HC1, was reported by Andrew and Weiss (17). CTC-HC1 is an amphoteric substance and consequently it is soluble in aqueous acid and base. However, it can rapidly degrade in these solvents. Its solubility in water is about 8 mg/ml and in methanol about 17 mg/ml. In higher molecular weight alcohols, the solubility of CTC-HC1 is considerably less than in methanol. For practical purposes, it is insoluble in many common solvents such as the aliphatic hydrocarbons, benzene, ether, and chloroform. It is readily soluble in pyridine and to the extent of about 5 mg/ml in formamide. Pyridine is an undesirable solvent because of its basicity, and formamide is not desirable because of the difficulty in obtaining and maintaining it as a stable solvent. 

The species Y is also probably non-existent in most of the enzyme catalysed reactions involving only one substrate. In acidic or basic reactions, Y and W do, however, play roles. In acid catalysed reactions, where C is an acid, transfer of proton to S takes place giving Y as a conjugate base of C. W is a basic or amphoteric substance which accepts a proton from X. In base catalysis, Y is a conjugate acid to the base C while W transfers a proton to X and may be the solvent or another acidic substance. With regard to the stability of the intermediate complex X, the two possibilities, which may be considered, are ... 

The amphoteric character of water (i.e., the ability to act either as an acid or as a base) makes water so special. While this renders the use of water as a solvent in acid-or base-sensitive reactions problematic, the possibility to have the solvent as a reactant in acid- or base-initiated reactions is often desirable. These qualities led chemists to rediscover water as a solvent in organic chemistry. Unfortunately, from a chemical point of view, not all transformations are feasible in aqueous solvent systems. Many reagents decompose when brought into contact with water while many others are insoluble. Consequently, it is not surprising that water has not been a very popular solvent in organic chemistry in the past, but this picture is changing rapidly. 

It is very instructive to compare the kinetics and plausible mechanisms of reactions catalyzed by the same or related catalyst(s) in aqueous and non-aqueous systems. A catalyst which is sufficiently soluble both in aqueous and in organic solvents (a rather rare situation) can be used in both environments without chemical modifications which could alter its catalytic properties. Even then there may be important differences in the rate and selectivity of a catalytic reaction on going from an organic to an aqueous phase. TTie most important characteristics of water in this context are the following polarity, capability of hydrogen bonding, and self-ionization (amphoteric acid-base nature). 

Quinolone carboxylic acid antibacterials are synthetic compounds whose basic nuclear structure includes a quinolone ring and a carboxylic acid group. Fluoroquinolones are second-generation quinolones that contain in their molecule a fluorine and a piperazine ring. Quinolones are amphoteric compounds slightly soluble in polar solvents such as water, and insoluble in nonpolar solvents such as benzene and hexane. Most of these drugs are fluorescent and are quite stable in aqueous solution toward light, except miloxacin, which is reported to be unstable. 

Tetracycline antibiotics are closely related derivatives of the polycyclic naphtha-cenecarboxamide. They are amphoteric compounds with characteristic dissociation constants corresponding to the acidic hydroxyl group at position 3 (pK about 3.3), die dimethylamino group at position 4 (pK, about 7.5), and the hydroxyl group at position 12 (pK about 9.4). In aqueous solutions of pH 4-7, tetracyclines exist as dipolar ions, but as the pH increases to 8-9 marked dissociation of the dimethylamine cation occurs. They are soluble in acids, bases, and alcohols but are quite insoluble in organic solvents such as chloroform. Their ultraviolet spectra show strong absorption at around 270 and 360 nm in neutral and acidic solutions. Tetracyclines are readily transformed into fluorescent products in the presence of metal ions or under alkaline conditions. 

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