110-18-9Relevant articles and documents
Copper(I) halide complexes with N,N′-diallyl-N,N,N′,N′- tetramethylethylenediaminium (L2+). Synthesis and crystal structures of the complexes [L0.5CuCl2], [L0.5CuCl 0.72Br1.28], and [L0.5CuBr2]
Monchak,Goreshnik,Mys'Kiv
, p. 143 - 148 (2011)
The Eschweiler-Clarke reaction of ethylenediamine with formaldehyde and formic acid yielded N,N,N′,N′-tetramethylethylenediamine, which was alkylated with allyl chloride or allyl bromide to give the corresponding N,N′-diallyl-N,N,N′,N′-tetramethylethylenediaminium (L 2+) dihalides. In methanolic solutions of copper(II) halide and an appropriate ligand, ac electrochemical synthesis with copper wire electrodes afforded single crystals of Cu(I) complexes with L2+: [L 0.5CuCl2] (I), [L0.5CuCl0.72Br 1.28] (II), and [L0.5CuBr2] (III). The crystal structures of complexes I-III were determined by X-ray diffraction study. The isostructural crystals of I and II are monoclinic, space group P21/n, Z = 4. For I: a = 7.632(4) A, b = 11.318(5) A, c = 10.635(5) A, β = 98.551(7)°, V = 908.4(7) A3. For II: a = 7.7415(7) A, b = 11.4652(9) A, c = 10.7267(10) A, β = 98.351(4)°, V = 942.0(2) A3. The organic cation L 2+ acts as a bridge linking a pair of separate cuprous halide fragments Cu2X4. Although being isostoichiometric with I and II, complex III has a different structure. The crystals of III are monoclinic, space group P21/c, a = 6.519(2) A, b = 9.060(3) A, c = 16.284(6) A, β = 97.219(4)°, V = 954.2(6) A3, Z = 4. In structure III, the inorganic fragment forms infinite polymer chains (CuBr 2 - ) n . The organic and inorganic parts are held together only by electrostatic interactions. Structures I-III are stabilized by hydrogen bonds (C)H...X (2.6-2.9 A).
REACTIONS OF ZINC HYDRIDE AND MAGNESIUM HYDRIDE WITH PYRIDINE; SYNTHESIS AND CHARACTERIZATION OF 1,4-DIHYDRO-1-PYRIDYLZINC AND -MAGNESIUM COMPLEXES
Koning, A. J. De,Boersma, J.,Kerk, G. J. M. van der
, p. 159 - 172 (1980)
The synthesis and characterization of 1,4-dihydro-1-pyridylzinc and -magnesium complexes are described.Zinc hydride and magnesium hydride dissolve in and react with pyridine, and the reaction has been studied in detail in the case of zinc hydride.Evaporation of the solvent after 1-2 hours at 0 deg C yielded a product containing pyridine, a 1,4-dihydropyridyl moiety and zinc hydrogen bonds, and two alternative structures are proposed for this complex.When the reaction was carried on for a long period, a yellow precipitate began to separate after about 40 hours, andreaction was complete after 7 days.The yellow product was identified as the pyridine complex of bis(1,4-dihydro-1-pyridyl)zinc.The corresponding magnesium complex was obtained from the reaction between magnesium hydride and pyridine for 50 hours at room temperature.
Dimethyl(N,N,N′,N′-tetramethylethanediamine)palladium(II) and dimethyl[1,2-bis(dimethylphosphino)ethane]palladium(II): Syntheses, X-ray crystal structures, and thermolysis, oxidative-addition, and ligand-exchange reactions
De Graaf, Wim,Boersma, Jaap,Smeets, Wilberth J. J.,Spek, Anthony L.,Van Koten, Gerard
, p. 2907 - 2917 (1989)
PdMe2(tmeda) (2a) (tmeda = N,N,N′,N′-tetramethylethanediamine) has been prepared and characterized by means of NMR spectroscopy and X-ray crystallography. Crystals of PdMe2(tmeda) are monoclinic, space group P21/n, with un
Cleavable cationic antibacterial amphiphiles: Synthesis, mechanism of action, and cytotoxicities
Hoque, Jiaul,Akkapeddi, Padma,Yarlagadda, Venkateswarlu,Uppu, Divakara S. S. M.,Kumar, Pratik,Haldar, Jayanta
, p. 12225 - 12234 (2012)
The development of novel antimicrobial agents having high selectivity toward bacterial cells over mammalian cells is urgently required to curb the widespread emergence of infectious diseases caused by pathogenic bacteria. Toward this end, we have developed a set of cationic dimeric amphiphiles (bearing cleavable amide linkages between the headgroup and the hydrocarbon tail with different methylene spacers) that showed high antibacterial activity against human pathogenic bacteria (Escherichia coli and Staphylococcus aureus) and low cytotoxicity. The Minimum Inhibitory Concentrations (MIC) were found to be very low for the dimeric amphiphiles and were lower or comparable to the monomeric counterpart. In the case of dimeric amphiphiles, MIC was found to decrease with the increase in the spacer chain length (n = 2 to 6) and again to increase at higher spacer length (n > 6). It was found that the compound with six methylene spacers was the most active among all of the amphiphiles (MICs = 10-13 μM). By fluorescence spectroscopy, fluorescence microscopy, and field-emission scanning electron microscopy (FESEM), it was revealed that these cationic amphiphiles interact with the negatively charged bacterial cell membrane and disrupt the membrane integrity, thus killing the bacteria. All of the cationic amphiphiles showed low hemolytic activity (HC50) and high selectivity against both gram-positive and gram-negative bacteria. The most active amphiphile (n = 6) had a 10-13-fold higher HC50 than did the MIC. Also, this amphiphile did not show any cytotoxicity against mammalian cells (HeLa cells) even at a concentration above the MIC (20 μM). The critical micellar concentration (CMC) values of gemini surfactants were found to be very low (CMC = 0.30-0.11 mM) and were 10-27 times smaller than the corresponding monomeric analogue (CMC = 2.9 mM). Chemical hydrolysis and thermogravimetric analysis (TGA) proved that these amphiphiles are quite stable under both acidic and thermal conditions. Collectively, these properties make the newly synthesized amphiphiles potentially superior disinfectants and antiseptics for various biomedical and biotechnological applications.
Antibacterial and Antibiofilm Activity of Cationic Small Molecules with Spatial Positioning of Hydrophobicity: An in Vitro and in Vivo Evaluation
Hoque, Jiaul,Konai, Mohini M.,Sequeira, Shanola S.,Samaddar, Sandip,Haldar, Jayanta
, p. 10750 - 10762 (2016)
More than 80% of the bacterial infections are associated with biofilm formation. To combat infections, amphiphilic small molecules have been developed as promising antibiofilm agents. However, cytotoxicity of such molecules still remains a major problem. Herein we demonstrate a concept in which antibacterial versus cytotoxic activities of cationic small molecules are tuned by spatial positioning of hydrophobic moieties while keeping positive charges constant. Compared to the molecules with more pendent hydrophobicity from positive centers (MIC = 1-4 μg/mL and HC50 = 60-65 μg/mL), molecules with more confined hydrophobicity between two centers show similar antibacterial activity but significantly less toxicity toward human erythrocytes (MIC = 1-4 μg/mL and HC50 = 805-1242 μg/mL). Notably, the optimized molecule is shown to be nontoxic toward human cells (HEK 293) at a concentration at which it eradicates established bacterial biofilms. The molecule is also shown to eradicate preformed bacterial biofilm in vivo in a murine model of superficial skin infection.
Modulation spectroscopy. Kinetics for the self-reactions of some α-aminoalkyl radicals in solution
Marriott, Paul R.,Castelhano, Arlindo L.,Griller, David
, p. 274 - 278 (1982)
The optical spectra and reaction kinetics of some α-aminoalkyl radicals, RCHN(CH2R)2; R = H, Me, Ph, were measured in solution using the technique of modulation spectroscopy.These radicals undergo diffusion controlled self-reaction with rate constants ca. 109 M-1 s-1.When R=Ph, the absorption spectrum has a well defined maximum at 346 nm; ε = 3390 M-1 cm-1, while the spectra when R = H or Me were less intense (ε346nm ca. 500 M-1 cm-1) and tailed into the visible.These spectra are substantially red-shifted when compared with those of simple alkyl radicals, an effect which is thought to be due to the interaction between the unpaired electron and the lone pair of electrons on nitrogen.
Unusual reactivity patterns of 1,3,6,8-tetraazatricyclo-[4.4.1.1 3,8]-dodecane (TATD) towards some reducing agents: Synthesis of TMEDA
Rivera, Augusto,Rios-Motta, Jaime
, p. 1471 - 1481 (2007)
N,N,N′,N′-Tetramethylethylenediamine (TMEDA) can be synthesized by simple reduction of 1,3,6,8-tetraazatricyclo-[4.4.1.1.3,8] dodecane (TATD), an aminal cage type amine, with formic acid. The aminal can be converted to TMEDA in high yield very easily and in a very short time. We comment on the scope and limitations of the reduction of this aminal and propose a possible reaction mechanism.
Boron-nitrogen compounds. CXX. Complexes of B-triethylboroxin with ethylenediamine and derivatives thereof
Mariategui, J. Francisco,Niedenzu, Kurt
, p. 137 - 146 (1989)
B-Triethylboroxin forms colorless 1/1 molar complexes of the type (C2H5BO)3.L with L=ethylenediamine (1) and various derivatives of the latter, i.e., N,N-dimethylethylenediamine (2), N,N,N',N'-tetramethylethylenediamine (3), piperazine (4), 1,4-diazabicyclooctane (5), diethylenetriamine (6), and tris(2-aminoethyl)amine (7).The cited boroxin also forms 2/1 molar complexes, 2(C2H5BO)3.L, with L=ethylenediamine (8) and those derivatives of the latter which may be considered as symmetrical species, i.e., N,N,N',N'-tetramethylethylenediamine (9), piperazine (10), 1,4-diazabicyclooctane (11), and diethylenetriamine (12).NMR spectroscopic data suggest that the complexes are fluxional in solution at room temperature with a single nitrogen coordinating to the three boron atoms of a given boroxin ring and where, in solution, the 1/1 molar complexes of symmetrical amines appear to exchange their donor sites.There seem to be no principal differences in the complexing of (RBO)3 with R=C2H5 or C6H5.Two species of the unusual composition 3(RBO)3.2H2NCH2NH2 were also identified.
COMPLEXES OF 9-PROPYLFLUORENYL ION PAIRS WITH TERTIARY POLYAMINES IN APOLAR SOLVENTS
Helary, G.,Lefevre-Jenot, L.,Fontanille, M.,Smid, J.
, p. 139 - 146 (1981)
The complexation of tetramethylethylenediamine (TMEDA), hexamethyltriethylenetetramine (HMTT) and tetramethyltetraazacyclotetradecane (TMTCT) with ion pairs of 9-(n-propyl)fluorenyllithium (PFl-, Li+) and n-butyl-9-(n-propyl)fluorenylmagnesium (BuPFlMg) in cyclohexane was studied by optical spectroscopy.The results can be explained in terms of externally complexed tight ion pairs and ligand-separated ion pairs, the latter complexes being much less soluble.With HMTT and PFl-, Li+, the only complexes formed are (PFl-, Li+)2 HMTT (λm 357 nm) and PFl-, HMTT, Li+ (λm 383 nm).The reaction of PFl-, Li+, TMEDA with TMTCT to form the loose ion pair complex PFl-, TMTCT, Li+ has a rate constant in toluene of 250 M-1 sec-1.With the magnesium compound, the amines form only a loose ion pair complex, e.g., BuMg+, TMEDA, PFl- (λm 382 nm).
PROCESS FOR PREPARING N-SUBSTITUTED ALKANOLAMINES AND/OR N-SUBSTITUTED DIAMINES FROM GLYCOLALDEHYDE
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A process for preparing a N-substituted alkanolamine of formula (I) and/or a N-substituted diamine of formula (II) from glycolaldehyde is provided, which comprises reacting glycolaldehyde with an aminating agent of formula (III) in a solvent comprising at least one C1-C3 alkanol and/or tetrahydrofuran in the presence of hydrogen and a supported noble metal catalyst, wherein in formulas (I) - (III) : R and R', independently from each other, represent hydrogen, linear or branched C1-C20 alkyl, C3-C12 cycloalkyl, C2-C30 alkoxyalkyl, or C3-30 dialkylaminoalkyl, provided that at least one of R and R' is not hydrogen.
