7545-59-7Relevant articles and documents
Corrosion inhibition performance of newly synthesized 5-alkoxymethyl-8-hydroxyquinoline derivatives for carbon steel in 1 M HCl solution: Experimental, DFT and Monte Carlo simulation studies
El Faydy,Touir,Ebn Touhami,Zarrouk,Jama,Lakhrissi,Olasunkanmi,Ebenso,Bentiss
, p. 20167 - 20187 (2018/08/16)
Three new organic compounds primarily based on 8-hydroxyquinoline have been successfully synthesized and characterized via different spectroscopic methods (FTIR, 1H, and 13C NMR). The synthesized compounds, namely 5-propoxymethyl-8-hydroxyquinoline (PMHQ), 5-methoxymethyl-8-hydroxyquinoline (MMHQ) and 5-hydroxymethyl-8-hydroxyquinoline (HMHQ), were evaluated as corrosion inhibitors for carbon steel in 1 M HCl solution using electrochemical impedance spectroscopy, potentiodynamic polarization and weight loss measurements at 298 K. Electrochemical measurements confirmed that the newly synthesized 5-alkoxymethyl-8-hydroxyquinoline derivatives are mixed type corrosion inhibitors and confirmed maximum protection efficiencies of 94, 89 and 81% for PMHQ, MMHQ, and HMHQ, respectively, at the optimum concentration of 10-3 M. The EIS spectra confirmed a slightly depressed semi-circle profile with a single time constant in Bode diagrams for the three organic compounds over the whole concentration and temperature ranges studied. The adsorption of PMHQ, MMHQ, and HMHQ on the carbon steel surface followed the Langmuir adsorption isotherm. In addition, the kinetic and thermodynamic parameters for carbon steel corrosion and inhibitor adsorption, respectively, were determined and discussed. Scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS) analyses supported the formation of a protective film on carbon steel in the presence of PMHQ, MMHQ, and HMHQ. Density functional theory calculations (DFT) showed that the effectiveness of the inhibitive actions of the studied compounds correlates well with their electron donating ability, whilst Monte Carlo simulations revealed that the extent and favourability of adsorption of inhibitor molecules on the carbon steel surface establish their corrosion inhibition performances.
Intermolecular interactions in the solid state structures of neutral and N-protonated 5-alkoxymethyl-8-hydroxyquinolines
Schulze, Mathias M.,B?hme, Uwe,Schwarzer, Anke,Weber, Edwin
, p. 307 - 319 (2016/12/18)
A series of five different alkoxymethyl substituted derivatives of 8-hydroxyquinoline was synthesised both in protonated (1a-1e) and neutral (2a-2e) form. The alkoxymethyl groups are MeO (1a, 2a), EtO (1b, 2b), n-PrO (1c, 2c), iso-PrO (1d, 2d), n-BuO (1e, 2e). The compounds were characterised by single crystal X-ray diffraction and spectroscopic methods. Hirshfeld surface analysis was performed to analyse the crystal packing quantitatively. Topological analysis of the electron density distribution delivers information about the strength of the hydrogen bonds. The overall results reveal a main difference between the charged (1a-1d) and uncharged (2a-2e) compounds in the orientation of the hydroxyl group resulting in a different cyclic dimer formation. In both cases the structures are dominated by hydrogen bonding (1a-1d: O[sbnd]H?Cl, N[sbnd]H?Cl and 2a-2e: O[sbnd]H?N). Furthermore, all crystal structures show π involved interactions though taking only a minor part in the packing of the molecules.
Microwave assisted synthesis of a small library of substituted N, N ′-Bis((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ethers
Farruggia, Giovanna,Iotti, Stefano,Lombardo, Marco,Marraccini, Chiara,Petruzziello, Diego,Prodi, Luca,Sgarzi, Massimo,Trombini, Claudio,Zaccheroni, Nelsi
supporting information; experimental part, p. 6275 - 6278 (2010/12/19)
Figure presented. N,N′-Bis-((8-hydroxy-7-quinolinyl)methyl)-1,10- diaza-18-crown-6 ether 1a and its analogue 1c are known as fluorescent sensors of magnesium in living cells. With the aim to investigate the effects of the substitution pattern on the photophysical properties of ligands 1 and their metal complexes, we developed an efficient microwaves enhanced one-pot Mannich reaction to double-armed diaza-crown ligands 1 carrying a variety of substituents. This new protocol is characterized by shorter reaction times, enhanced yields, and improved product purities with respect to the use of conventional conductive heating.
