4107-98-6Relevant articles and documents
Substituent Effects. 7. Microscopic Dissociation Constants of 4-Amino- and 4-(Dimethylamino)benzoic Acid
Graaf, B.van de,Hoefnagel, A. J.,Wepster, B. M.
, p. 653 - 657 (1981)
The termodynamic microscopic dissociation constants of the title compounds have determined from the two macroscopic constants K1 and K2 and KA, the carboxylic acid dissociation constant of the cation.The latter were calculated by starting from the experimental value for 4-(trimethylammonio)benzoic acid using our knowledge of the substituent effects of charged substituents.In water, the zwitterion equilibrium contains 10.5percent zwitterion for 4-aminobenzoic acid and 19.4percent for 4-(dimethylamino)benzoic acid.In 50percent and 75percent ethanol the zwitterion content is very low.Extended Hine equations are applied to show the contributions of the several substituent interactions in the individual species, and to predict the percent zwitterion in other acids.Glycine is also discussed.In water, ?-4-NH2 = -0.62 and ?-4-NMe2 = -0.69; the latter value is rather different from that commonly tabulated.
Preparation method of N-alkylated derivative of primary amine compound
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Paragraph 0021; 0057, (2021/07/09)
The invention relates to a preparation method of an N-alkylated derivative of a primary amine compound. The method comprises the following steps: uniformly mixing a primary amine compound, an alcohol compound and a catalyst in a reactor, and heating to react for a period of time to generate an N-alkylated substituted tertiary amine compound; wherein the catalyst is a copper-cobalt bimetallic catalyst, and the carrier of the catalyst is Al2O3. According to the method, alcohol is adopted as an alkylating reagent and is low in price and easy to obtain, a byproduct is water, no pollution is caused to the environment, and the overall reaction atom economy is high; the catalyst is simple in preparation method, low in cost, high in reaction activity and good in structural stability; meanwhile, by using the copper-cobalt bimetallic catalyst, the use of strong base additives can be avoided, and the requirement on reaction equipment is low; and the reaction post-treatment is convenient, and the catalyst can be recycled and is environment-friendly.
N-Arylphenothiazines as strong donors for photoredox catalysis – pushing the frontiers of nucleophilic addition of alcohols to alkenes
Speck, Fabienne,Rombach, David,Wagenknecht, Hans-Achim
supporting information, p. 52 - 59 (2019/01/28)
A new range of N-phenylphenothiazine derivatives was synthesized as potential photoredox catalysts to broaden the substrate scope for the nucleophilic addition of methanol to styrenes through photoredox catalysis. These N-phenylphenothiazines differ by their electron-donating and electron-withdrawing substituents at the phenyl group, covering both, σ and π-type groups, in order to modulate their absorbance and electrochemical characteristics. Among the synthesized compounds, alkylaminylated N-phenylpheno-thiazines were identified to be highly suitable for photoredox catalysis. The dialkylamino substituents of these N-phenylpheno-thiazines shift the estimated excited state reduction potential up to ?3.0 V (vs SCE). These highly reducing properties allow the addition of methanol to α-methylstyrene as less-activated substrate for this type of reaction. Without the help of an additive, the reaction conditions were optimized to achieve a quantitative yield for the Markovnivkov-type addition product after 20 h of irradiation.
