52411-33-3Relevant articles and documents
Azo-azomethine dyes with N, O, S donor set of atoms and their Ni(II) complexes: Synthesis, characterization and spectral properties
Khanmohammadi, Hamid,Rezaeian, Khatereh,Amini, Mostafa M.,Ng, Seik Weng
, p. 557 - 564 (2013)
New azo-azomethine dyes, L1-L3, with N 2S2O2 donor set of atoms have been synthesized via condensation reaction of 1,2-bis(2-aminophenylthio)ethane with 5-(4-X-phenyl)-azo-salicylaldehyde (X = Cl, OMe and Me). The new dyes were characterized by IR, UV-Vis, 1H NMR and fluorescence spectroscopy as well as mass spectrometry and elemental analysis. Mononuclear nickel(II) complexes of the dyes have been also prepared. The crystal structure of [NiL1]·0.5H2O was determined by single-crystal X-ray diffraction. The thermal analysis data indicate that all prepared dyes, L1-L3, are thermally stable up to 320 C. The fluorescence behavior of the prepared complexes have been also investigated and compared to those of L1-L3.
SYNTHESIS OF MACROHETEROCYCLES, ANALOGS OF DIBENZO-CROWN COMPOUNDS. 1. 15-MEMBERED OXATHIADIAMINES
Formanovski, A. A.,Murakhovskaya, A. S.
, p. 225 - 229 (1985)
Macrocyclic diamides have been synthesized by the condensation of 1,4-bis(2-aminophenyl)-1,4-dioxa(dithia)butanes with the diacid chlorides of glutaric, diglycolic, and thiodiglycolic acids under conditions of high dilution.Subsequent reduction with diborane led to the corresponding macrocyclic diamine containing atoms of oxygen and (or) sulfur.Structural assignments were made using data of mass spectrometry and IR, PMR, and 13C NMR spectra.
Development of a scaleable synthesis for 1,2-bis(2-aminophenylthio)ethane (APO-Link) used in the production of bismaleimide resin
Densmore, Crystal G.,Wheeler, Hilary,Cohenour, Rebecca,Robison, Thomas W.,Hasam, Dawud,Cordova, Blossom J.,Stark, Peter C.,Fuller, Edward N.,Cook, Charles J.,Weber, Holly A.
, p. 996 - 1003 (2007)
The diamine reagent 1,2-bis(2-aminophenylthio)ethane is no longer commercially available but is still required for the synthesis of the bismaleimide resin, APO-BMI, used in syntactic foams. In this work, we examined the hydrolysis of benzothiazole followed by reaction with dichloroethane or dibromoethane. The deprotonation of 2-aminothiophenoI followed by reaction with dibromoethane was also investigated and later optimized for scale-up by scrutinizing all aspects of the reaction conditions, work-up, and recrystallization. On bench-scale, the optimized procedure consistently produced a 75-80% overall yield of finely divided, high purity product (>95%). The material was also produced on both a 100 Ib scale and a 200 Ib scale using the optimized process, giving high quality material in excellent yield.
NSSN-Type Group 4 Metal Complexes in the Ring-Opening Polymerization of l -Lactide
Impemba, Salvatore,Roviello, Giuseppina,Milione, Stefano,Capacchione, Carmine
, p. 7561 - 7572 (2021)
A new class of zirconium and hafnium complexes coordinated by linear dianonic tetradentate NSSN ligands is reported. The ligands feature two amide functions coupled with two thioether groups linked by a central flexible ethane bridge and two lateral rigid phenylene bridges and differ for the substituents on the aniline nitrogen atoms, i.e., isopropyl, cyclohexyl, or mesityl substituents: NSSN-iPr, NSSN-Cy, or NSSN-Mes. They were prepared by reacting 2-aminothiophenol with dibromoethane to afford the NSSN ligands without substituents on the aniline nitrogen atoms, which were subsequently alkylated through a reductive amination of acetone or cyclohexanone or palladium-catalyzed cross-coupling reaction with mesityl bromide. The corresponding zirconium and hafnium complexes 1-5 were obtained through a transamination reaction between the neutral ligands and Zr(NMe2)4 or Hf(NMe2)4 [(NSSN-iPr)Zr(NMe2)2 (1), (NSSN-Cy)Zr(NMe2)2 (2), (NSSN-Mes)Zr(NMe2)2 (3), (NSSN-iPr)Hf(NMe2)2 (4), and (NSSN-Cy)Hf(NMe2)2 (5)]. They were characterized in solution by NMR spectroscopy and in solid state by X-ray diffraction analysis (except for 3). All complexes present an octahedral coordination geometry with a fac-fac ligand wrapping and a cis relationship between the other two monodentate ligands. The catalytic performances of 1-5 in the ring-opening polymerization of cyclic esters were investigated. Complex 1 was the most active: its polymerization activity was superior to those generally displayed by zirconium complexes featuring OSSO ligands and compared well with those of the most active group 4 complexes operating in a toluene solution.
Synthesis and characterization of a thioether Schiff base ligand and its metal complexes and crystal structure determination of the nickel(II) complex
Dehghani-Firouzabadi, Ahmad Ali,Kargar, Hadi,Eslaminejad, Safie,Notash, Behrouz
, p. 4345 - 4354 (2015)
Reactions of 1,2-di(o-aminophenylthio)ethane with 3-ethoxy-2-hydroxybenzaldehyde yield the new hexadentate N2S2O2 donor thioether Schiff base 1,2-bis(2-((2-(thio)phenylimino)methyl)-6-ethoxyphenol)ethane (H2L). Ni(II), Zn(II), Cd(II), and Hg(II) complexes of this ligand were prepared. Of these complexes, [NiL]·2H2O has been structurally characterized by X-ray crystallography. The coordination geometry around Ni(II) was described as octahedral. Zn(II), Cd(II), and Hg(II) complexes and the Schiff base ligand have been characterized by CHN analyses, molar conductivity, UV-vis, FT-IR, 1H, and 13C NMR spectroscopy.
Metal induced enhancement of fluorescence and modulation of two-photon absorption cross-section with a donor-acceptor-acceptor-donor receptor
Das, Sanjib,Nag, Amit,Sadhu, Kalyan K.,Goswami, Debabrata,Bharadwaj, Parimal K.
, p. 4969 - 4977 (2007)
A metal ion sensing fluorophore L that exhibits a large two-photon absorption cross-section has been synthesized in good yields. The influences of different metal ion inputs, on the one- and two-photon spectroscopic properties of L, have been investigated. The ligand itself does not show any fluorescence although in presence of a metal ion like Zn(II), Cd(II), Mg(II) or Ca(II), a ～25 time enhancement of fluorescence is observed. The ligand with symmetrical "donor-acceptor-acceptor-donor" characteristics exhibits a large two-photon absorption cross-section measured by femtosecond open-aperture Z-scan technique at 880 nm. However, presence of any of the above metal ions lowers its two-photon absorption cross-section (δ) to different extents at 880 nm. Theoretical calculation carried out in DFT formalism on the ligand and its Zn(II) complex corroborate experimental results.
In Vitro Antimicrobial and in Vivo Molluscicidal Potentialities of Fe(III), Co(II) and Ni(II) Complexes Incorporating Symmetrical Tetradentate Schiff bases (N2O2)
Alosaimi, Amal M.,Mannoubi, Ines El,Zabin, Sami A.
, p. 373 - 384 (2020/07/23)
This paper aimed at synthesizing symmetrical Schiff base ligands derived from the primary amine 1,2-bis(2-aminophenylthio)ethane condensed with 7-formyl-8-hydroxyquinoline and 2-hydroxy-1-naphthaldehyde. The synthesised ligands were used for preparing metal complexes with the iron triad metals. The symmetrical tetradentate (N2O2) Schiff base ligands SL1 and SL2 forms mononuclear complexes with square planar geometry in case of Co(II) and Ni(II) complexes, while an octahedral geometry was obtained for the Fe(III) complexes. The molar conductance quantification showed that the complexes were non-ionic. In vitro antimicrobial potential examination of the free ligands indicated weak activity and the corresponding complexes showed enhanced activity. Moreover, the In vivo molluscicidal potential of the tested chemicals showed good activity against the tested land snails. Ligands showed activity at concentration of 1000 ppm while their metal complexes show activity at concentration of 500 ppm. The highest activity (LC50) of complexes was shown at concentration of 5000 ppm.
Photocatalytic and electrocatalytic hydrogen production using nickel complexes supported by hemilabile and non-innocent ligands
Inoue, Satoshi,Yan, Yin-Nan,Yamanishi, Katsunori,Kataoka, Yusuke,Kawamoto, Tatsuya
supporting information, p. 2829 - 2832 (2020/03/19)
Nickel complexes with non-innocent ligands generated by one-electron reduction of octahedral Schiff base nickel(ii) complexes with hemilabile ligands exhibited excellent catalytic activities of over 5000 TONs through a metal-ligand cooperation mechanism for hydrogen evolution from water under visible light irradiation.
Bis(2-cyanoacetamides): Versatile precursors for bis(dihydropyridine-3,5-dicarbonitriles)
Sanad, Sherif M.H.,Elwahy, Ahmed H.M.,Abdelhamid, Ismail A.
, p. 39 - 49 (2018/10/26)
Bis(6-amino-1,2-dihydropyridine-3,5-dicarbonitriles) containing thioether linkages are prepared via the condensation of bis(cyanoacetamides) with α-substituted cinnamonitriles in the presence of piperidine. The target compounds can also be obtained via a three-component reaction of bis(cyanoacetamides) with two equivalents of both aldehydes and malononitrile in ethanol containing piperidine as a base.
Zinc oxide catalyzed solvent-free mechanochemical route for C-S bond construction: A sustainable process
Md. Khaja Mohinuddin,Gangi Reddy
, p. 1207 - 1214 (2017/12/07)
A zinc oxide catalyzed solvent-free mechanochemical process has been developed for the rapid construction of C-S bonds by using a nucleophilic substitution reaction (SN2 mechanism) that involves a variety of thiols and phenacyl/ benzyl/alkyl bromides. Notable advantages of this method in-clude its broad substrate scope, clean reaction profile, safety, scalability, high product yields at ambient conditions, and the recyclability of the catalyst. Furthermore, the prepared compounds are valuable building blocks for the synthesis of various biologically active molecules.
