Synthesis and Keto‐Enol Tautomerism in N‐(2‐Hydroxy‐1‐Naphthylidene)Anils

Ünver, Hüseyin; Polat, Kamran; Uçar, Mustafa; Zengin, Dursun

doi:10.1081/sl-120024579

Cited by 25 publications

(16 citation statements)

References 23 publications

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“…In addition the characteristic broad band at the 3100 -3000 cm -1 region corresponding to the intra-molecular hydrogen bonding and the bands between the 1700 -1600 cm -1 region due to C=N and C=O stretching 23 were found to disappear. The principal mass spectral peaks observed were as follows: The molecular ion peaks corresponding to the dimerized product were observed in the MS spectra of all compounds.…”

Section: Controlled-potential Preparative Electrolyses and Mechanism mentioning

confidence: 93%

“…23 These compounds are listed in Table 1. The given melting points, relate to a reversible, true melting process.…”

Section: Reagentsmentioning

confidence: 99%

“…23 This study is concerned with an examination of their electrochemical behaviors. The synthesized Schiff bases were examined by the cyclic voltammetric, chronoamperometric and coulometric methods and the electroreduction products were investigated by using spectroscopic methods in order to determine the electrochemical mechanism.…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical Reduction of 1-{[(4-Halophenyl)imino]methyl}-2-naphthols in Aprotic Media

et al. 2004

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The electrochemical reduction of 1-{[(4-halophenyl)imino]methyl}-2-naphthols on graphite electrodes was studied using cyclic voltammetry, chronoamperometry, constant-potential coulometry and preparative constant-potential electrolysis techniques. The data revealed that the reduction on graphite was irreversible and followed an EC mechanism. The diffusion coefficients and the number of electrons transferred were determined using the chronoamperometric Cottrell slope and the ultramicro disc Pt-electrode steady-state current. The number of electrons was also determined by bulk electrolysis. The compounds were subjected to constant-potential preparative electrolysis and the electrolysis products were purified and identified by spectroscopic methods. Based on these findings, a mechanism for the electro-reduction process is proposed.

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Section: Controlled-potential Preparative Electrolyses and Mechanism mentioning

confidence: 93%

“…23 These compounds are listed in Table 1. The given melting points, relate to a reversible, true melting process.…”

Section: Reagentsmentioning

confidence: 99%

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Electrochemical Reduction of 1-{[(4-Halophenyl)imino]methyl}-2-naphthols in Aprotic Media

et al. 2004

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“…The low melting point of 3 may be explained by keto-enol tautomerism. A large number of Schiff bases was structurally determined so far, revealing that crystal structures of compounds of this class were dominated by the O-H···N (enol-imino) tautomeric form [44,45]. Some of Schiff bases exhibit the N-H···O tautomers [46][47][48][49][50][51] and their common feature is the presence of a hydroxyl [46,[49][50][51] or a nitro group [47,48] at the N-phenyl ring or the phenyl ring of parent aldehyde.…”

Section: Melting Pointsmentioning

confidence: 99%

<b>Synthesis, spectral characterizations and antimicrobial activity of some Schiff bases of 4-chloro-2-aminophenol</b>

Çınarli¹,

Gürbüz²,

Tavman³

et al. 2011

Bull. Chem. Soc. Eth.

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ABSTRACT ABSTRACT. A series of 4-chloro-2-[(arylmethylidene)amino]phenols (1-11) including methoxy group were synthesized using appropriate synthetic route. The structures of the Schiff bases were characterized by FT-IR, UV-Vis, ESI-MS, 1 H and 13 C-NMR spectroscopic techniques and analytical methods. A relation is observed between melting points and existence of intramolecular hydrogen bonding. IR spectra of the compounds including and not including hydrogen bonding were compared. The compounds 2 and 4 show the characteristic UV bands attributed to the NH-forms. According to the 1 H-NMR spectral data the compound 2 has the strongest intramolecular hydrogen bonding and the compound 6 shows two isomeric structure. On the other hand, antibacterial and antifungal activities of the compounds were investigated. Most of the compounds show selective activity toward S. epidermidis and C. albicans. KEY WORDS KEY WORDS KEY WORDS

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“…Schiff bases have a wide range of applications in the fields of coordination chemistry, biochemistry, pharmacy, nanotechnology, optical devices and textiles [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. In particular, the ortho-hydroxy class of Schiff bases has been attractive for physicists and chemists for many years because of its interesting photochromic and thermochromic features in the solid state.…”

Section: Introductionmentioning

confidence: 99%

Crystal structure, spectral characterization, molecular modeling studies and structural effects of the proton transfer process for (E)-5-methoxy-2-[(3,4-dimethylphenylimino) methyl]phenol

Kırca

Tarı

Kaştaş

et al. 2017

Maced. J. Chem. Chem. Eng.

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The main purpose of this study is to characterize a new organic material, (E)-5-methoxy-2-[(3,4-dimethylphenylimino)methyl]phenol, which was synthesized and grown as a single crystal. The molecular structure and spectroscopic properties of the ortho-hydroxy Schiff base compound were determined by X-ray diffraction analysis, Fourier-transform infrared (FT-IR), ultraviolet-visible (UV-Vis) and nuclear magnetic resonance (NMR) spectroscopy techniques, experimentally and computationally with density functional theory (DFT) calculations. X-ray and UV-Vis studies show that the compound exists in an OH tautomeric form in the solid and solvent media. The gas phase geometry optimizations of two possible forms of the title compound, resulting from the prototropic tautomerism, were obtained using DFT calculations at the B3LYP/6-311G+(d,p) level of theory. A relaxed potential energy surface (PES) scan was performed based on the optimized geometry of the OH tautomeric form by varying the redundant internal coordinate, the O-H bond distance. According to the PES scan process, the molecular geometry is strongly affected by the intramolecular proton transfer. The calculated first hyperpolarizability indicates that the compound could be a good material for non-linear optical applications.Keywords: Schiff base; prototropic tautomerism; intramolecular proton transfer; NLO; DFT КРИСТАЛНА СТРУКТУРА, СПЕКТРАЛНА КАРАКТЕРИЗАЦИЈА, СТУДИИ ЗА МОЛЕКУСКО МОДЕЛИРАЊЕ И СТРУКТУРНИ ЕФЕКТИ ОД ПРОЦЕСОТ НА ПРОТОН ТРАНСФЕР ЗА (E)-5-МЕТОКСИ-2-[(3,4-ДИМЕТИЛФЕНИЛИМИНО)МЕТИЛ]ФЕНОЛГлавна цел на ова истражување е да се карактеризира нов органски материјал, (E)-5-метокси-2-[(3,4-диметилфенилимино)метил]фенол, што беше синтетизиран и израснат како монокристал. Молекулската структура и спекторскопските својства на орто-хидрокси Шифовата база беа определени експериментално со помош на рендгенска дифракциска анализа, Фуриеова трансформна инфрацрвена спектроскопија (FTIR), ултравиолетова спектроскопија (UV-Vis) и нуклеарно-магнетна спектроскопска анализа и пресметковно со помош на теоријата на густината на функционалот (DFT). Испитувањата со рендгенската дифракција и UV-Vis покажуваат дека соединението постои во OH тавтомерна форма во цврста состојба и во раствор. Геометриската оптимизација во гасна фаза на двете можни форми на наведеното соединение кои се резултат на прототропен тавтомеризам беа добиени со пресметки според DFT на нивото на теоријата B3LYP/6-311G+(d,p). Скенирањето на површината на релаксираната потенцијална енергија (PES) беше изведено врз оптимизираната геометрија на ОН тавтомерната форма со менување на редундантната внатрешна координата, должината на О-Н врската. Според скенот на процесот на РЕЅ, молекулската геометрија е под силно влијание на интрамолекулскиот B. K. Kırca, G. Ö. Tarı, Ç. A. Kaştaş, M. Odabaşoğlu, O. Büyükgüngö Maced. J. Chem. Chem. Eng. 36 (1), xx-xx (2017) 266 трансфер на протони. Пресметаната прва хиперполаризабилност укажува дека соединението би било добар материјал за нелинеарни оптички апликации.Клучни зборови: Шиф...

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Synthesis and Keto‐Enol Tautomerism in N‐(2‐Hydroxy‐1‐Naphthylidene)Anils

Cited by 25 publications

References 23 publications

Electrochemical Reduction of 1-{[(4-Halophenyl)imino]methyl}-2-naphthols in Aprotic Media

Electrochemical Reduction of 1-{[(4-Halophenyl)imino]methyl}-2-naphthols in Aprotic Media

<b>Synthesis, spectral characterizations and antimicrobial activity of some Schiff bases of 4-chloro-2-aminophenol</b>

Crystal structure, spectral characterization, molecular modeling studies and structural effects of the proton transfer process for (E)-5-methoxy-2-[(3,4-dimethylphenylimino) methyl]phenol

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