3,3,3-Trifluoro-N′-(3-trifluoromethylphenyl)-1,2-propanediamine and its N-mono-and N,N-dicarboxyethyl derivatives: synthesis, protolytic and complexation properties

被引:0
|
作者
V. Yu. Korotaev
Yu. A. Skorik
A. Yu. Barkov
M. I. Kodess
A. Ya. Zapevalov
机构
[1] A. M. Gorky Ural State University,Department of Chemistry
[2] University of Pittsburgh,I. Ya. Postovsky Institute of Organic Synthesis
[3] Ural Branch of the Russian Academy of Sciences,undefined
来源
Russian Chemical Bulletin | 2005年 / 54卷
关键词
3,3,3-trifluoro-; ′-(3-trifluoromethylphenyl)-1,2-propanediamine; 3-[2-(3-tri-fluoromethylphenylamino)-3,3,3-trifluoropropylamino]propionic acid; 3,3-[2-(3-trifluoro-methylphenylamino)-3,3,3-trifluoropropylamino]dipropionic acid; carboxyethylation; protolytic equilibria; complexation; transition metal ions; selectivity;
D O I
暂无
中图分类号
学科分类号
摘要
3,3,3-Trifluoro-N′-(3-trifluoromethylphenyl)-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.
引用
收藏
页码:2545 / 2549
页数:4
相关论文
共 50 条
  • [1] 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, 54 (11) : 2545 - 2549
  • [2] SYNTHESIS OF ISOMERIC N-BENZYL DERIVATIVES OF 1,2-PROPANEDIAMINE
    KURGANOV, A
    ZHUCHKOVA, L
    DAVANKOV, V
    LIEBIGS ANNALEN DER CHEMIE, 1980, (05): : 786 - 790
  • [3] STUDIES ON STABILITY OF MIXED COPPER(2) COMPLEXES OF ALIPHATIC DIAMINES .3. ETHYLENEDIAMINE N,N'-DIMETHYLETHYLENEDIAMINE N,N'-DIETHYLETHYLENEDIAMINE 1,2-PROPANEDIAMINE AND 1,3-PROPANEDIAMINE AS LIGANDS
    NASANEN, R
    TILUS, P
    SUOMEN KEMISTILEHTI, 1969, 42 (01): : 11 - &
  • [4] Acetone [μ-N,N′-bis(3-methoxy-2-oxido-benzylidene)-1,2-propanediamine]-trinitratocopper(II) praseodymium (III)
    Sun, Wen-Bin
    Ting, Gao
    Yan, Peng-Fei
    Li, Guang-Ming
    Hou, Guang-Feng
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : M2192 - U1535
  • [5] Synthesis and herbicidal activities of novel 3-N-substituted amino-6-methyl-4-(3-trifluoromethylphenyl)pyridazine derivatives
    Xu, Han
    Hu, Xu-Hong
    Zou, Xiao-Mao
    Liu, Bin
    Zhu, You-Quan
    Wang, Yong
    Hu, Fang-Zhong
    Yang, Hua-Zheng
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (15) : 6567 - 6572
  • [6] N-MONO AND N1N3-DIALKYLATION OF METHYL AND DODECYL UROCANATES, SYNTHESIS OF AMPHIPHILIC DERIVATIVES
    MONJE, MC
    MAWLAWI, H
    LATTES, A
    RIVIERE, M
    NEW JOURNAL OF CHEMISTRY, 1993, 17 (03) : 231 - 235
  • [7] 4-(3-Trifluoromethylphenyl)-pyrimidine-2-carbonitrile as cathepsin S inhibitors: N3, not N1 is critically important
    Cai, Jiaqiang
    Fradera, Xavier
    van Zeeland, Mario
    Dempster, Maureen
    Cameron, Kenneth S.
    Bennett, D. Jonathan
    Robinson, John
    Popplestone, Lucy
    Baugh, Mark
    Westwood, Paul
    Bruin, John
    Hamilton, William
    Kinghorn, Emma
    Long, Clive
    Uitdehaag, Joost C. M.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (15) : 4507 - 4510
  • [8] Copolymerization of 3,3,3-trifluoro-1,2-epoxypropane with N-phenylmaleimide using organozine initiators
    Ikeda, Y
    Yoshida, Y
    Ishihara, K
    MACROMOLECULAR RAPID COMMUNICATIONS, 1996, 17 (10) : 713 - 721
  • [9] A bis(acetylacetonato)uranium(IV) complex of the Schiff base N,N′-bis(3-hydroxysalicylidene)-2-methyl-1,2-propanediamine
    Salmon, L
    Thuéry, P
    Ephritikhine, M
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2003, 59 : M246 - M248
  • [10] CRYSTAL AND MOLECULAR-STRUCTURE AND SYNTHESIS OF (E)-N,N-DIMETHYL-2-TRIFLUOROMETHYL-3-(3,3,3-TRIFLUORO-2-TRIFLUOROMETHYLPROP-1-ENYLOXY)ACRYLAMIDE
    CHEKHLOV, AN
    POPOV, AV
    PUSHIN, AN
    DOKLADY AKADEMII NAUK, 1993, 331 (01) : 62 - 65