Reactions of 2‐(diformylmethylidene)‐3,3‐dimethylindole with hydrazides: Synthesis of new pyrazolylindolenine derivatives—the unprecedented one‐pot pyrazole–thiadiazole double annulation

Khaledi, Hamid; Ali, Hapipah Mohd; Thomas, Noel F.; Ng, Seik Weng

doi:10.1002/jhet.575

Cited by 5 publications

(2 citation statements)

References 21 publications

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“…Beberapa penelitian telah dilakukan kajian terhadap sifat anti korosi turunan senyawa pirazolindol [11][12][13][14]. Pirazolindol adalah senyawa heterosiklik aromatik yang memiliki cincin pirol dan cincin indol.…”

Section: Pendahuluanunclassified

Optimasi Sifat Inhibitor Korosi Senyawa Thiaamida-Pirazolindol Berdasarkan Teori Fungsional Kerapatan

Hamdiani¹,

Arduha²,

Purwoko³

et al. 2016

J. Pijar MIPA

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Abstrak. Sifat inhibitor korosi senyawa turunan thiaamida-pirazolindol (TP) telah dikaji menggunakan teori fungsional kerapatan pada tingkatan teori B3LYP/6-31G(d). Pengaruh gugus substitusi pendonor dan penarik elektron (NH2, SH, CHCH2, CH3, OH, CHO, COOH, F, NO2) terhadap efisiensi anti korosi senyawa thiaamidapirazolindol juga dihitung. Parameter kuantum untuk senyawa anti korosi seperti energi orbital (EHOMO dan ELUMO), potensial ionisasi (I), afinitas elektron (A) dan elektronegativitas (χ) memiliki hubungan yang linier dengan efisiensi anti korosi (IE%) senyawa turunan thiaamida-pirazolindol. Gugus pendonor elektron meningkatkan nilai IE%. Urutan kenaikan IE% adalah NO2 < CHO < COOH < F < CHCH2 < OH < CH3 < NH2. Penambahan gugus pendonor elektron amina (NH2) meningkatkan IE% hingga 98,76 % dibandingkan IE% thiaamida-pirazolindol murni 90,80 %. Penambahan gugus penarik elektron menurunkan IE% hingga mencapai 82,82 %. Kajian teoritis ini akan berkontribusi besar dalam mendesain dan sintesis senyawa inhibitor organik dengan efisiensi inhibitor tinggi.Kata kunci: inhibitor korosi, teori fungsional kerapatan, thiaamida-pirazolindol Abstract. Corrosion inhibitor properties of thiamide pyrazolindole and its derivatives has been elucidated by means of density functional theory (DFT) at B3LYP/6-31G(d) level of theory. Effect of electron donating and withdrawing groups such as NH2, SH, CHCH2, CH3, OH, CHO, COOH, F and NO2 on the corrosion inhibitor of thiamide pyrazolindole derivatives also have been studied. The quantum chemical parameters such as the frontier orbital energies (EHOMO), ionization potential (I), electron affinity (A) and electronegativity (χ) are closely related to the corrosion inhibition efficiency (IE%) of thiamide pyrazolindole derivatives. The presence of electron donating groups increases IE% values meanwhile electron withdrawing groups reduce IE% values. The enhancement of IE% follows NO2 < CHO < COOH < SH < F < CH3 < CHCH2 < OH < NH2. Electron donating NH2 group gives 98,76 % of IE%, pure thiamide pyrazolindol IE% = 90,80 %. In contrast, electron withdrawing NO2 group gives IE% only 82,82 %. This theoretical study would have a significant contribution in designing high-efficiency organic corrosion inhibitors.

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Section: Pendahuluanunclassified

Optimasi Sifat Inhibitor Korosi Senyawa Thiaamida-Pirazolindol Berdasarkan Teori Fungsional Kerapatan

Hamdiani¹,

Arduha²,

Purwoko³

et al. 2016

J. Pijar MIPA

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“…We have recently reported the synthesis and the structures of new pyrazolylindolenine compounds which are 4-(3,3-dimethyl-3 H -indol-2-yl)-pyrazole-1-carbothioamide (InPzTAm), 4-(3,3-dimethyl-3 H -indol-2-yl)-1 H -pyrazole-1-carbothiohydrazi (InPzTH) and 3, 3-dimethyl-2-(1-phenyl-1 H -pyrazol-4-yl)-3 H -indole (InPzPh) [11]. The corrosion inhibition properties of these compounds on copper surface in hydrochloric acid media are investigated using electrochemical impedance spectroscopy (EIS), open circuit potential (OCP), and field emission scanning electron microscopy (FESEM) techniques.…”

Section: Introductionmentioning

confidence: 99%

Corrosion inhibition properties of pyrazolylindolenine compounds on copper surface in acidic media

Ebadi

Basirun

Khaledi

et al. 2012

Chemistry Central Journal

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BackgroundThe corrosion inhibition performance of pyrazolylindolenine compounds, namely 4-(3,3-dimethyl-3H-indol-2-yl)-pyrazole-1-carbothioamide (InPzTAm), 4-(3,3-dimethyl-3H-indol-2-yl)-1H-pyrazole-1-carbothiohydrazide (InPzTH) and 3,3-dimethyl-2-(1-phenyl-1H-pyrazol-4-yl)-3H-indole (InPzPh),) on copper in 1M HCl solution is investigated by electrochemical impedance spectroscopy (EIS), open circuit potential (OCP) and linear scan voltammetry (LSV) techniques.ResultsThe results show that the corrosion rate of copper is diminished by the compounds with the inhibition strength in the order of: InPzTAm> InPzTH > InPzPh. The corrosion inhibition efficiencies for the three inhibitors are 94.0, 91.4 and 79.3, for InPzTAm, InPzTH and InPzPh respectively with the same inhibitor concentration (2 mM).ConclusionFrom the EIS, OCP and LSV results it was concluded that pyrazolylindolenine compounds with S-atom (with an amine group) have illustrated better corrosion inhibition performance compared to hydrazine and phenyl group.

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ChemInform Abstract: Reactions of 2‐(Diformylmethylidene)‐3,3‐dimethylindole with Hydrazides: Synthesis of New Pyrazolylindolenine Derivatives — The Unprecedented One‐Pot Pyrazole—Thiadiazole Double Annulation.

et al. 2011

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Reactions of 2‐(diformylmethylidene)‐3,3‐dimethylindole with hydrazides: Synthesis of new pyrazolylindolenine derivatives—the unprecedented one‐pot pyrazole–thiadiazole double annulation

Cited by 5 publications

References 21 publications

Optimasi Sifat Inhibitor Korosi Senyawa Thiaamida-Pirazolindol Berdasarkan Teori Fungsional Kerapatan

Optimasi Sifat Inhibitor Korosi Senyawa Thiaamida-Pirazolindol Berdasarkan Teori Fungsional Kerapatan

Corrosion inhibition properties of pyrazolylindolenine compounds on copper surface in acidic media

ChemInform Abstract: Reactions of 2‐(Diformylmethylidene)‐3,3‐dimethylindole with Hydrazides: Synthesis of New Pyrazolylindolenine Derivatives — The Unprecedented One‐Pot Pyrazole—Thiadiazole Double Annulation.

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