New strategy of synthesis, characterization, theoretical study and inhibition effect on mild steel corrosion in acidic solution

We report two new different synthesis strategies of an eco-friendly organic dye 3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl diacetate. These methods were based on the reaction of fluorescein with acetic anhydride under different experimental conditions. The synthesized heterocyclic system obtained with excellent yield was characterized by FT-IR, 1 H N.M.R., 13 C N.M.R., and mass spectrometry. This reaction has also been studied theoretically using Gaussian 09 based on the DFT method at B3LYP/6-31G (d, p). The results obtained are in good correlation with those obtained experimentally. The inhibition behavior of the synthetic product has been studied using absorbance difference measurement, the percentage of inhibition efficiency attains 90% at 10 -4 M of NAR3 inhibitor. The surface analysis of mild steel was investigated using scanning electron microscopy (S.E.M.) and Energy Dispersive X-ray (E.D.X.) methods and show the adsorption behavior of inhibitor on the surface of mild steel.

[1]  Kaixian Chen,et al.  Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of N-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1H)-One Scaffolds , 2020, Molecules.

[2]  M. Baroncini,et al.  Photo- and Redox-Driven Artificial Molecular Motors. , 2020, Chemical reviews.

[3]  K. Alzoubi,et al.  Synthesis, Characterization, Antimicrobial Activity, and Genotoxicity Assessment of Two Heterocyclic Compounds Containing 1,2,3-Selena- or 1,2,3-Thiadiazole Rings , 2019, Molecules.

[4]  A. Singh,et al.  Experimental, theoretical, and surface study for corrosion inhibition of mild steel in 1 M HCl by using synthetic anti-biotic derivatives , 2019, Ionics.

[5]  R. Singh,et al.  Medicinal chemistry of indole derivatives: Current to future therapeutic prospectives. , 2019, Bioorganic chemistry.

[6]  N. Arshad,et al.  Furan and Phenyl Substituted Triazolothiadiazine Derivatives as Copper Corrosion Inhibitors: Electrochemical and DFT Studies , 2019, Protection of Metals and Physical Chemistry of Surfaces.

[7]  M. Polz-Dacewicz,et al.  The influence of some promising fused azaisocytosine‐containing congeners on zebrafish (Danio rerio) embryos/larvae and their antihaemolytic, antitumour and antiviral activities , 2019, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[8]  D. Spinelli,et al.  Synthesis and antimicrobial activity of new derivatives of pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidine and new heterocyclic systems , 2019, Synthetic Communications.

[9]  Ezeibe A.U.  Thermodynamics Study of Inhibitory Action of Lignin Extract from Gmelina arborea on the Corrosion of Mild Steel in Dilute Hydrochloric Acid , 2019 .

[10]  M. Taleb,et al.  A Review on the Assessment of Imidazo[1,2-a]pyridines As Corrosion Inhibitor of Metals , 2018, Journal of Bio- and Tribo-Corrosion.

[11]  M. Taleb,et al.  Corrosion Resistance of Mild Steel Coated with Orgainc Material Containing Pyrazol Moiety , 2018, Coatings.

[12]  O. Silakari,et al.  Triazoles: Multidimensional 5-Membered Nucleus for Designing Multitargeting Agents , 2018 .

[13]  D. Spinelli,et al.  Synthesis and antimicrobial activity of new amino derivatives of pyrano , 2018 .

[14]  D. Spinelli,et al.  Synthesis and antimicrobial activity of new amino derivatives of pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidine. , 2018, Anais da Academia Brasileira de Ciências.

[15]  P. Diana,et al.  An overview on the recent developments of 1,2,4-triazine derivatives as anticancer compounds. , 2017, European journal of medicinal chemistry.

[16]  J. F. Stoddart,et al.  Introducing Stable Radicals into Molecular Machines , 2017, ACS central science.

[17]  J. Frère,et al.  1,2,4‐Triazole‐3‐thione Compounds as Inhibitors of Dizinc Metallo‐β‐lactamases , 2017, ChemMedChem.

[18]  S. Chafaa,et al.  Synthesis, antibacterial screening and DFT studies of series of α-amino-phosphonates derivatives from aminophenols , 2017 .

[19]  Z. Deng,et al.  Synthesis and biological evaluation of salinomycin triazole analogues as anticancer agents. , 2017, European journal of medicinal chemistry.

[20]  K. M. Fazili,et al.  Synthesis and biological evaluation of novel 3-O-tethered triazoles of diosgenin as potent antiproliferative agents , 2017, Steroids.

[21]  S. Sirakanyan,et al.  Synthesis and Anticonvulsant Activity of 7(8)-Amino Derivatives of Condensed Thieno[3,2-d]Pyrimidines , 2016, Pharmaceutical Chemistry Journal.

[22]  M. H. Franz,et al.  Novel 1,2,4-oxadiazoles and trifluoromethylpyridines related to natural products: synthesis, structural analysis and investigation of their antitumor activity , 2016 .

[23]  A. Foroumadi,et al.  The importance of triazole scaffold in the development of anticonvulsant agents. , 2016, European journal of medicinal chemistry.

[24]  Sundus Erbas-Cakmak,et al.  Artificial Molecular Machines , 2015, Chemical reviews.

[25]  E. Mabrouk,et al.  Synthesis of new racemic α-heterocyclic α,α-diaminoesters and α-aminoester carboxylic , 2013 .

[26]  J. F. Stoddart,et al.  Radically enhanced molecular switches. , 2012, Journal of the American Chemical Society.

[27]  L. Domingo,et al.  The nucleophilicity N index in organic chemistry. , 2011, Organic & biomolecular chemistry.

[28]  R. Kharb,et al.  Pharmacological significance of triazole scaffold , 2011, Journal of enzyme inhibition and medicinal chemistry.

[29]  E. Ebenso,et al.  Titanium (IV) Oxide as Corrosion Inhibitor for Aluminium and Mild Steel in Acidic Medium , 2010, International Journal of Electrochemical Science.

[30]  A. Alami,et al.  One-pot regioselective synthesis of n-benzoyl 2-amino-3,4-dihydro-3-oxo-2h-1,4-benzothiazines , 2010 .

[31]  David M. Shackleford,et al.  Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice. , 2009, Journal of medicinal chemistry.

[32]  L. Domingo,et al.  A condensed-to-atom nucleophilicity index. An application to the director effects on the electrophilic aromatic substitutions , 2009 .

[33]  M. Choudhary,et al.  Syntheses, urease inhibition, and antimicrobial studies of some chiral 3-substituted-4-amino-5-thioxo-1H,4H-1,2,4-triazoles. , 2008, Medicinal chemistry (Shariqah (United Arab Emirates)).

[34]  A. Alami,et al.  Synthesis and Thermal Isomerization of Carboxylic and Phosphonic α-Aminoesters Substituted With a Triazole Ring , 2007 .

[35]  M. Cǎproiu,et al.  Synthesis of New Active o-Nitrophenyl Carbamates , 2005 .

[36]  Markus Sauer,et al.  Spectroscopic study and evaluation of red-absorbing fluorescent dyes. , 2003, Bioconjugate chemistry.

[37]  J P McNamee,et al.  Photophysical Properties of Fluorescent DNA-dyes Bound to Single- and Double-stranded DNA in Aqueous Buffered Solution¶ , 2001, Photochemistry and photobiology.

[38]  Ming-Der Chen,et al.  Synthesis and Antibacterial Activity of some Heterocyclic β-Enamino Ester Derivatives with 1,2,3-triazole , 2000 .

[39]  F. E. Jorge,et al.  Accurate universal Gaussian basis set for all atoms of the Periodic Table , 1998 .

[40]  Paul M. S. Monk,et al.  The Viologens: Physicochemical Properties, Synthesis and Applications of the Salts of 4,4'-Bipyridine , 1998 .