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Substituent effects amino groups

The amino group activates the thiazole ring toward electrophilic centers. This point is illustrated by the rate constants of the reaction between 2-dialkylaminothiazoles (32) and methyl iodide in nitromethane at 25 C (Scheme 23) (158). The steric effects of substituents on nitrogen are... [Pg.32]

Regarding the substituent effect on reactivity of groups in positions 4 and 5 there is little information in the literature. The reactivity of halogen in position 5 seems to be increased when an amino group is present in position 2. Substitution products are easily obtained using neutral nucleophiles such as thiourea, thiophenols, and mercaptans (52-59). [Pg.572]

Historically, the discovery of one effective herbicide has led quickly to the preparation and screening of a family of imitative chemicals (3). Herbicide developers have traditionally used combinations of experience, art-based approaches, and intuitive appHcations of classical stmcture—activity relationships to imitate, increase, or make more selective the activity of the parent compound. This trial-and-error process depends on the costs and availabiUties of appropriate starting materials, ease of synthesis of usually inactive intermediates, and alterations of parent compound chemical properties by stepwise addition of substituents that have been effective in the development of other pesticides, eg, halogens or substituted amino groups. The reason a particular imitative compound works is seldom understood, and other pesticidal appHcations are not readily predictable. Novices in this traditional, quite random, process requite several years of training and experience in order to function productively. [Pg.39]

Ultraviolet. Benzene has a series of relatively low intensity absorption bands in the region of 230 to 270 nm. When there is a substituent on the ring with nonbonding electrons, such as an amino group, there is a pronounced increase in the intensity of these bands and a shift to longer wavelength. Aniline shows an absorption band at 230 nm (e = 8600) and a secondary band at 280 nm (e = 1430). Protonation of the amino groups reduces these effects and the spectmm resembles that of the unsubstituted benzene. [Pg.232]

Whereas introducing a thiol moiety at C-7 markedly reduced the antibacterial activity relative to lincomycin (79), the 7(3)-7-deoxy-7-alkylthiolincomycins exhibited considerably enhanced antibacterial activity without apparent regard for the size of the alkyl group (80—82). A marked increase in gram-negative activity was shown when the 7(3)-substituent contained a 2- or 3-hydroxy or amino group, but this activity was insufficient to be effective in infected mice (83—85). [Pg.90]

As might be expected from a consideration of electronic effects, an amino substituent activates pyrazines, quinoxalines and phenazines to electrophilic attack, usually at positions ortho and para to the amino group thus, bromination of 2-aminopyrazine with bromine in acetic acid yields 2-amino-3,5-dibromopyrazine (Scheme 29). [Pg.177]

The effect of substituents on the reactivity of heterocyclic nuclei is broadly similar to that on benzene. Thus mem-directing groups such as methoxycarbonyl and nitro are deactivating. The effects of strongly activating groups such as amino and hydroxy are difficult to assess since simple amino compounds are unstable and hydroxy compounds exist in an alternative tautomeric form. Comparison of the rates of formylation and trifiuoroacetylation of the parent heterocycle and its 2-methyl derivative indicate the following order of sensitivity to substituent effects furan > tellurophene > selenophene = thiophene... [Pg.44]

Ring substituents can have a considerable effect on the acidity of the system. In the 1,2,4-triazole series a 3-amino group decreases the acidity to 11.1, a 3-methyl group to 10.7, whereas a 3-phenyl group Increases the acidity to 9.6, and 3,5-dlchloro substitution to 5.2 (71PMH(3)1). [Pg.51]

A mechanism has been proposed to rationalize the results shown in Figure 23. The relative proportion of the A -pyrazolines obtained by the reduction of pyrazolium salts depends on steric and electronic effects. When all the substituents are alkyl groups, the hydride ion attacks the less hindered carbon atom for example when = Bu only C-5 is attacked. The smaller deuterohydride ion is less sensitive to steric effects and consequently the reaction is less selective (73BSF288). Phenyl substituents, both on the nitrogen atom and on the carbon atoms, direct the hydride attack selectively to one carbon atom and the isolated A -pyrazoline has the C—C double bond conjugated with the phenyl (328 R or R = Ph). Open-chain compounds are always formed during the reduction of pyrazolium salts, becoming predominant in the reduction of amino substituted pyrazoliums. [Pg.243]

Notice that the MO picture gives the same qualitative picture of the substituent effects as described by resonance structures. The amino group is pictured by resonance as an electron donor which causes a buildup of electron density at the /3 carbon, whereas the formyl group is an electron acceptor which diminishes electron density at the /3 carbon. [Pg.49]

With 1-hydroxytryptophan derivatives, similar substituent effects are observed (99H2815). In order to realize better yields of 5-substituted tryptophans, car-boxy and amino groups are transformed to ester and/or amide groups, choosing the 1-methoxy moiety as a leaving group. As a result, ( )-Ab-acetyl-5-chlorotryptophan methyl ester (219, 52%) is obtained together with 220 (7%) from ( )-218 by the reaction with aqueous HCl (Scheme 32). ( )-5-Bromo-Ab-methoxycarbonyltryptophan methylamide (222, 50%) becomes readily available... [Pg.132]

The relative insensitivity of Sp to changes in electronegativity of substituents which is observed for P fluoro-compounds is also evident for penta-arylphosphoranes. Thus the placement of />ara-substituents on the phenyl rings of pentaphenylphosphorane has very little effect and Sp is -f 88 1 p.p.m. for (16 Y = H, Me, or Cl). The effect on Sp of the introduction of an amino-group in the bis-biphenylenephosphorane system (17) is similar to that of an alkyl group (see Table 3). ... [Pg.252]


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Amino effect

Amino groups substituents

Amino substituents

Groups substituents

Substituent groups

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