3,3,3-Trifluoro-N `-(3-trifluoromethylphenyl)-1,2-propanediamine and its N-mono- and N,N-dicarboxyethyl derivatives: synthesis, protolytic and complexation properties / Korotaev VY,Skorik YA,Barkov AY,Kodess MI,Zapevalov AY // RUSSIAN CHEMICAL BULLETIN. - 2005. - V. 54, l. 11. - P. 2545-2549.

ISSN/EISSN:

1066-5285 / нет данных

Type:

Article

Abstract:

3,3,3-Trifluoro-N'-(3-trifloromethylphenyl)- 1,2-propanediamine (5) was synthesized by the reaction of 2-diazo-1,1,1-trifluoro-3-nitropropane or 3,3,3-trifluoro-1-nitropropene with 3-aminobenzotrifluoride followed by the reduction of the nitro group. The Michael 1,4-addition of diamine 5 to acrylic acid occurs only at the N(1) atom and affords N-mono- or N,N-dicarboxyethyl derivatives 6 and 7, depending on the reactant ratio. Protolytic equilibria 5-7 in aqueous solutions were Studied by pH-potentiometry and UV spectroscopy. Only the aliphatic amino group can be protonated in an aqueous solution, while the aromatic amino group remains Unprotonated even in 12 M HCl. The stability constants of transition metal (Cu2+, Ni2+, Zn2+) complexes with ligands 5-7 were determined by pH-potentiometric titration. The stability of the complexes and selectivity of the ligands toward Cu2+ ions increase with an increase in the number of N-carboxyethyl groups.

Author keywords:

3,3,3-trifluoro-N `-(3-trifluoromethylphenyl)-1,2-propanediamine; 3-{[}2-(3-trifluoromethylphenylamino)-3,3,3-trifluoropropylamino]propion ic acid; 3,3-{[}2-(3-trifluoromethylphenylamino)-3,3,3-triflu ACID

DOI:

10.1007/s11172-006-0153-y

Web of Science ID:

ISI:000237178200011

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV
Publisher	CONSULTANTS BUREAU/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	ACID
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	Vladislav.Korotaev@usu.ru skorik@pitt.edu nmr@ios.uran.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016 Skorik, Yury/A-8128-2008
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Number-of-Cited-References	20
Usage-Count-Since-2013	2
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	037WK