Solubility in nonpolar solvents

Critical micelle concentration (Section 19 5) Concentration above which substances such as salts of fatty acids aggre gate to form micelles in aqueous solution Crown ether (Section 16 4) A cyclic polyether that via lon-dipole attractive forces forms stable complexes with metal 10ns Such complexes along with their accompany mg anion are soluble in nonpolar solvents C terminus (Section 27 7) The amino acid at the end of a pep tide or protein chain that has its carboxyl group intact—that IS in which the carboxyl group is not part of a peptide bond Cumulated diene (Section 10 5) Diene of the type C=C=C in which a single carbon atom participates in double bonds with two others... 

Liquid sulfur dioxide expands by ca 10% when warmed from 20 to 60°C under pressure. Pure liquid sulfur dioxide is a poor conductor of electricity, but high conductivity solutions of some salts in sulfur dioxide can be made (216). Liquid sulfur dioxide is only slightly miscible with water. The gas is soluble to the extent of 36 volumes pet volume of water at 20°C, but it is very soluble (several hundred volumes per volume of solvent) in a number of organic solvents, eg, acetone, other ketones, and formic acid. Sulfur dioxide is less soluble in nonpolar solvents (215,217,218). The use of sulfur dioxide as a solvent and reaction medium has been reviewed (216,219). 

Hydrophobic substances are soluble in nonpolar solvents, whereas their solubiUty in water is very limited. Many of these substances are also soluble in fats and Hpids and are also called hpophile compounds. Such substances have a tendency to avoid contact with water and to associate with a nonpolar, nonaqueous environment, such as a surface, eg, an organic particle, a particle containing organic material, or the lipid-containing biomass of an organism. 

Bromine is soluble in nonpolar solvents and in certain polar solvents such as alcohol and sulfuric acid. It is miscible with alcohol, ether, carbon disulfide, and many halogenated solvents. Bromine reacts with some of these solvents under certain conditions. 

Cyanamide is a weak acid with a very high solubility in water. It is completely soluble at 43°C, and has a minimum solubiUty (eutectic) at — 15°C. It is highly soluble in polar organic solvents, such as the lower alcohols, esters, and ketones, and less soluble in nonpolar solvents (4). 

Alkenes — Also known as olefins, and denoted as C H2 the compounds are unsaturated hydrocarbons with a single carbon-to-carbon double bond per molecule. The alkenes are very similar to the alkanes in boiling point, specific gravity, and other physical characteristics. Like alkanes, alkenes are at most only weakly polar. Alkenes are insoluble in water but quite soluble in nonpolar solvents like benzene. Because alkenes are mostly insoluble liquids that are lighter than water and flammable as well, water is not used to suppress fires involving these materials. Because of the double bond, alkenes are more reactive than alkanes. 

Solvent Effects on the Rate of Substitution by the S/s/2 Mechanism. Polar- solvents are required in typical bimolecular- substitutions because ionic substances, such as the sodium and potassium salts cited earlier in Table 8.1, are not sufficiently soluble in nonpolar-solvents to give a high enough concentration of the nucleophile to allow the reaction to occur at a rapid rate. Other than the requirement that the solvent be polar- enough to dissolve ionic compounds, however, the effect of solvent polarity on the rate of Sn2 reactions is small. What is most imporiant is whether or not the polar- solvent is protic or aprotic. 

Chemists and biochemists find it convenient to divide the principal organic substances present in cells into four main groups carbohydrates, proteins, nucleic acids, and lipids. Structural differences separate carbohydrates from proteins, and both of these are structurally distinct from nucleic acids. Lipids, on the other hand, are characterized by a physical property, their solubility in nonpolar solvents, rather than by their structure. In this chapter we have examined lipid molecules that share a common biosynthetic origin in that all their carbons are derived from acetic acid (acetate). The form in which acetate occurs in many of these processes is a thioester called acetyl coenzyme A. 

Crown ether (Section 16.4) A cyclic polyether that, via ion-dipole attractive forces, forms stable complexes with metal ions. Such complexes, along with their accompanying anion, are soluble in nonpolar solvents. 

As a matter of fact, the main advantage in comparison with HPLC is the reduction of solvent consumption, which is limited to the organic modifiers, and that will be nonexistent when no modifier is used. Usually, one of the drawbacks of HPLC applied at large scale is that the product must be recovered from dilute solution and the solvent recycled in order to make the process less expensive. In that sense, SFC can be advantageous because it requires fewer manipulations of the sample after the chromatographic process. This facilitates recovery of the products after the separation. Although SFC is usually superior to HPLC with respect to enantioselectivity, efficiency and time of analysis [136], its use is limited to compounds which are soluble in nonpolar solvents (carbon dioxide, CO,). This represents a major drawback, as many of the chemical and pharmaceutical products of interest are relatively polar. 

Insoluble in water but soluble in nonpolar solvents such as CCl4 or benzene. Iodine is typical of most molecular substances it is only slightly soluble in water (0.0013 mol/L at 25°C), much more soluble in benzene (0.48 mol/L). A few molecular substances, including ethyl alcohol, are very soluble in water. As you will see later in this section, such substances have intermolecular forces similar to those in water. 

In Figure 8-1 we show the chemical structure of m-LPPP. The increase in conjugation and the reduction of geometrical defects was the main motivation to incorporate a poly(/ -phenylene)(PPP) backbone into a ladder polymer structure [21]. Due to the side groups attached to the PPP main chain excellent solubility in nonpolar solvents is achieved. This is the prerequisite for producing polymer films of high optical quality. A detailed presentation of the synthesis, sample preparation,... 

Lipids have the common property of being relatively insoluble in water (hydrophobic) but soluble in nonpolar solvents. Amphipathic lipids also contain one or more polar groups, making them suitable as constituents of membranes at lipidiwater interfaces. 

Nonpolar solids are usually soluble in nonpolar solvents. 

The molecule, cw-5-pentacosene, C25H50 or CH3(CH2)3CH=CH(CH2)i8CH3, is a fairly high molecular weight non-polar compound. It should be a solid at room temperature, insoluble in water, and soluble in nonpolar solvents. 

The tertiary and quaternary amine bases are viscous liquids at room temperature and infinitely soluble in nonpolar solvents, but only slightly soluble in water. The solubility of the ion-pair RNH L in organic solvents depends on the chain length and on the counterion, LT the solubility of TLA HCl in wet benzene is 0.7 M, in cyclohexane 0.08 M, in CHCI3 1.2 M, and in CCI4 0.7 M. Nitrate and perchlorate salts are less soluble, as are lower molecular weight amines. 

Alcohols with three or fewer carbons atoms are miscible in water in all proportions. The solubility of alcohols in water decreases with increasing number of carbon atoms, so that alcohols with more than six carbon atoms are nearly insoluble. As the number of carbon atoms increases, the solubility in nonpolar solvents increases. 

Apart from the increased catalytic efficiency, this structure design produced two positive side effects. In contrast to monofunctional (thio)ureas, which exhibit low solubility in nonpolar solvents due to intermolecular hydrogen-bonding association, tertiary amine thioureas of type 12 revealed intramolecular hydrogen bonding between the amine group and the amide protons making these (thio)ureas soluble in nonpolar reaction media such as toluene. The analysis of the X-ray crystal-... 

Like dissolves like, and this is true with both polymers and smaller molecules. Thus linear amorphous polymers with nonpolar groups are typically soluble in nonpolar solvents with solubility parameter values within 1.8 H of that of the polymer. Thus polyisobutylene (PIB) is soluble in hot lubricating oils, and small amounts of high-molecular-weight PIB are used as viscosity improvers. 

C atom. Both are soluble in nonpolar solvents and insoluble in water, except that lower-molecular-weight alkenes are slightly more water-soluble because of attraction between the it bond and H,0. 

The solubility of molecules can be explained on the basis of the polarity of molecules. Polar, e.g. water, and nonpolar, e.g. benzene, solvents do not mix. In general, like dissolves like i.e., materials with similar polarity are soluble in each other. A polar solvent, e.g. water, has partial charges that can interact with the partial charges on a polar compound, e.g. sodium chloride (NaCl). As nonpolar compounds have no net charge, polar solvents are not attracted to them. Alkanes are nonpolar molecules, and are insoluble in polar solvent, e.g. water, and soluble in nonpolar solvent, e.g. petroleum ether. The hydrogen bonding and other nonbonding interactions between molecules are described in Chapter 2. 

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