Physical properties of amides

To name an amide, follow the steps on the next page. The Sample Problem that follows illustrates how to use these steps. Later, Table 1.14 describes some physical properties of amides. 

Polarity of functional group Because the nitrogen atom attracts electrons more strongly than carbon or hydrogen atoms, the C-N and N-H bonds are polar. As a result, the physical properties of amides are similar to the physical properties of carboxylic acids. 

Physical Properties of Amides Earlier in this chapter we connected the structure of amides to their reactivity in nucleophilic acyl substitution by emphasizing the interaction of the nitrogen lone pair with the carbonyl group. 

Physical Properties of Amides Earlier in this chapter (see Section 19.2) we noted several of the ways in which electron donation from nitrogen to the carbonyl group affects various structural features of amides. To review, the hybridization of nitrogen in amides is sp, and the bonds to nitrogen lie in the same plane. The CN bond is shorter in amides, and... 

Some of the physical properties of fatty acid nitriles are Hsted in Table 14 (see also Carboxylic acids). Eatty acid nitriles are produced as intermediates for a large variety of amines and amides. Estimated U.S. production capacity (1980) was >140, 000 t/yr. Eatty acid nitriles are produced from the corresponding acids by a catalytic reaction with ammonia in the Hquid phase. They have Httie use other than as intermediates but could have some utility as surfactants (qv), mst inhibitors, and plastici2ers (qv). 

The bulk physical properties of the polymers of the 2-cyanoacryhc esters appear in Table 2. AH of these polymers are soluble in /V-methy1pyrro1idinone, /V,/V-dimethy1foTm amide, and nitromethane. The adhesive bonding properties of typical formulated adhesives are Hsted in Table 3. 

Tables 1 and 2 Hst the important physical properties of formamide. Form amide is more highly hydrogen bonded than water at temperatures below 80°C but the degree of molecular association decreases rapidly with increa sing temperature. Because of its high dielectric constant, formamide is an excellent ionizing solvent for many inorganic salts and also for peptides, proteias (eg, keratin), polysaccharides (eg, cellulose [9004-34-6] starch [9005-25-8]) and resias.

Selected physical properties of various methacrylate esters, amides, and derivatives are given in Tables 1—4. Tables 3 and 4 describe more commercially available methacrylic acid derivatives. A2eotrope data for MMA are shown in Table 5 (8). The solubiUty of MMA in water at 25°C is 1.5%. Water solubiUty of longer alkyl methacrylates ranges from slight to insoluble. Some functionalized esters such as 2-dimethylaniinoethyl methacrylate are miscible and/or hydrolyze. The solubiUty of 2-hydroxypropyl methacrylate in water at 25°C is 13%. Vapor—Hquid equiUbrium (VLE) data have been pubHshed on methanol, methyl methacrylate, and methacrylic acid pairs (9), as have solubiUty data for this ternary system (10). VLE data are also available for methyl methacrylate, methacrylic acid, methyl a-hydroxyisobutyrate, methanol, and water, which are the critical components obtained in the commercially important acetone cyanohydrin route to methyl methacrylate (11). 

Derivatives. The dual functionaUty of trimellitic anhydride makes it possible to react either the anhydride group, the acid group, or both. Derivatives of trimellitic anhydride include ester, acid esters, acid chloride, amides, and amide—imides (136). Trimellitate esters are the most important derivatives, and physical properties of more significant esters are Hsted in Table 34. 

Many of the physical properties of fatty acid amides have been explained on the basis of the tautomeric stmctures ... 

The compounds Ln(C5H5)2Cl also have been made only with the lanthanides above samarium (772). These compounds are stable in the absence of air and moisture, sublime near 200 °C, are insoluble in non-polar solvents, and exhibit room temperature magnetic moments near the free ion values (772, 113). The chloride ion may be replaced by a variety of anions including methoxide, phenoxide, amide and carboxylate. Some of these derivatives are considerably more air-stable than the chloride — the phenoxide is reported to be stable for days in dry air. Despite their apparent stability, little is known about the physical properties of these materials. The methyl-substituted cyclopentadiene complexes are much more soluble in non-polar solvents than the unsubstituted species. Ebulliometric measurements on the bis(methylcyclopentadienyl)lanthanide(III) chlorides indicated the complexes are dimeric in non-coordinating solvents (772). A structmre analysis of the ytterbium member of this series has been completed (714). The crystal and molecular parameters of this and related complexes are compared in Table 5. 

TABLE 1. Physical Properties of Selected Polyhydroxyalkanoate Derivatives Containing Amide or Sulfonic Acid Components Prepared According to the Current Invention... 

Most local anesthetic agents consist of a lipophilic group (eg, an aromatic ring) connected by an intermediate chain via an ester or amide to an ionizable group (eg, a tertiary amine) (Table 26-1). In addition to the general physical properties of the molecules, specific stereochemical configurations are associated with differences in the potency of stereoisomers (eg, levobupivacaine, ropivacaine). Because ester links are more prone to hydrolysis than amide links, esters usually have a shorter duration of action. 

Thermal stability as measured by these ramped TGA experiments of the sort previously described are not the definitive test of a polymer s utility at elevated temperature. Rather, for a polymer to be useful at elevated temperatures, it must exhibit some significant retention of useful mechanical properties over a predetermined lifetime at the maximum temperature that will be encountered in its final end use application. While many of the bisbenzocyclobutene polymers have been reported in the literature, only a few have been studied in detail with regards to their thermal and mechanical performance at both room and elevated temperatures. Tables 7-10 show some of the preliminary mechanical data as well as some other physical properties of molded samples of polymers derived from amide monomer 32, ester monomer 40, diketone monomer 14 and polysiloxane monomer 13. The use of the term polyamide, ester etc. with these materials is not meant to imply that they are to be regarded as merely modified linear thermoplastics. Rather, these polymers are for the most part highly crosslinked thermosets. 

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