Amines and Nitriles

In water, tertiary amines form quaternary ammonium compounds, e. g. with methyl halogenides. In aqueous solution, secondary (aliphatic and aromatic) amines react with nitrous acid HONO (namely the nitrosonium ion NO ) as already mentioned (reaction 5.217) to generate nitrosamines  

As good electron donors, they are easily oxidable in solution, gaining derivates of hydroxylamine (NH2OH)  

In water, it seems that amines undergo more decomposition than in the gas phase and will be accumulated in the condensed phase. In southern Sweden, the major amines in both air and rain were trimethylamine and methylamine, but dimethylamine, diethylamine and triethylamine were also detected and individually quantified. The total amine concentration was 0.16-2.8 nmol m in air and 30-540 nM in rain (Gronberg et al. 1990). 

Amides (dimethyl formamide) were also detected in air (Howard 1990), whereas other amides have been found to be emitted in industrial processes (acetamide, acrylamide). The general fate of amines is similar to that of ammonia, i.e. reactions with OH. They do not photolyze. Because the C—H bond energy is smaller than the N—H bond, predominantly OH abstracts H from C—H (Chapter 5.7.2)  

The further fate is not explicitly known, but molecule rearrangements and/or the addition of O2, NO c and NO3 is possible. From secondary amines, azo compounds or organic hydrazines (derived from hydrazine N2H4) can be given  

The reduction of Fe(III) porphyrin hydroxides by the heterocyclic aromatic amines, pyridine, 1-methylimidazole, and derivatives takes place in toluene to give the bis-amine Fe(II) porphyrin complexes. The preliminary data suggest that the initial step is formation of a bis-amine Fe(III) complex. Electrochemical oxidation of [Os(II)(terpy)(bpy)(NH3)](PF6)2 in the presence of Et2NH or morpholine yielded bound nitrosoamine complexes, [Os(II)(terpy) (bpy)(N(0)NR2)]. The kinetics and stoichiometry of the reaction between 

A small but significant amount of ammonia is also consumed in the production of various amines and nitriles57. 

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It is also possible to prepare them from amino acids by the self-condensation reaction (3.12). The PAs (AABB) can be prepared from diamines and diacids by hydrolytic polymerization [see (3.12)]. The polyamides can also be prepared from other starting materials, such as esters, acid chlorides, isocyanates, silylated amines, and nitrils. The reactive acid chlorides are employed in the synthesis of wholly aromatic polyamides, such as poly(p-phenyleneterephthalamide) in (3.4). The molecular weight distribution (Mw/Mn) of these polymers follows the classical theory of molecular weight distribution and is nearly always in the region of 2. In some cases, such as PA-6,6, chain branching can take place and then the Mw/Mn ratio is higher. 

The nucleophiles that are used for synthetic purposes include water, alcohols, carboxylate ions, hydroperoxides, amines, and nitriles. After the addition step is complete, the mercury is usually reductively removed by sodium borohydride, the net result being the addition of hydrogen and the nucleophile to the alkene. The regio-selectivity is excellent and is in the same sense as is observed for proton-initiated additions.17... 

The thermal isomerization of higher terminal alkynes also delivered some allene, from 1-hexyne and 1-heptyne, for example, some 1,2-diene was formed [30]. With an ,/l-unsaturated unit in the alkyne 9, a photochemical isomerization to 10 was successful but delivered only a low yield and 11 as a significant side-product [31]. These reactions tolerate different functional groups alcohols, ethers or, as in 12, tertiary amines and nitriles have been used (Scheme 1.5) [32, 33],... 

The classes listed in Table 1-12 are families which exhibit the same regularity of boiling points, melting points, densities, and other properties seen in the hydrocarbon families we have already studied. Some of the families are named with characteristic suffixes while others have prefixes, or even separate words-in the names. For instance, alcohols are named with the suffix -ol. Ketones are named with the suffix -one. Amine and nitriles are named with the full suffix according to the family name. Ethers and halides usually have the full family name as a separate word, and nitro- and organometallic compounds have the prefix nitro- or the prefix corresponding to the hydrocarbon part of the organometallic molecule. 

Correlation of Qrlgoras Grigoras [25] derived a simple linear correlation to estimate V °(cm3 mol-1) for liquid compounds, including saturated, unsaturated, and aromatic hydrocarbons, alcohols, acids, esters, amines, and nitriles ... 

Bakhshi has published two articles on this subject with titles 1 - Average electric polarizabilities and magnetic susceptibilities of hydrocarbons, alcohols, ethers, aldehydes, ketones, amines and nitriles. 2- Double-zeta pseudopotential study of methyllithium, methylberyllium and dimethylberyllium. ... 

Mercuration of 1-alkenes in the presence of nucleophilic solvents such as alcohols, amines, and nitriles or in the presence of sodium azide provides convenient access to the corresponding ethers, amines, amides, " and azides. ... 

Strecker reaction The condensation of carbonyl compounds with amines and nitriles to afford a-amino nitriles. 446... 

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