Conformational Analysis, Infrared, and Fluorescence Spectra of 1-Phenyl-1,2-propandione 1-oxime and Related Tautomers: Experimental and Theoretical Study

Bekhradnia, Ahmadreza; Arshadi, Sattar

doi:10.1007/s00706-007-0657-7

Cited by 13 publications

(3 citation statements)

References 24 publications

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“…In addition, strong characteristic absorption due to NO stretching vibration is observed at 999 cm −1 and calculated at 1000 cm −1 , which consists of 62% NO stretching and 16% bending of CH aliph. [54,55,56,58]. A substantial change is also observed in the NO stretching; the NO absorptions occurred at 1218 cm −1 (calcd.…”

Section: Resultsmentioning

confidence: 98%

“…It can be seen that the experiment has a better correlation with the calculations. In the IR spectra of nppeieoH, the O–H stretching vibration of the oxime was calculated at 3659 cm −1 , while observed at 3258 cm −1 [54,55,56]. The deviation between the experimental and calculated values seems to be significant for the hydroxyl group frequencies with a difference of 401 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Spectroscopic, Structural and Quantum Chemical Studies of a New Imine Oxime and Its Palladium(II) Complex: Hydrolysis Mechanism

2016

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Abstract:In this work, we report synthesis, crystallographic, spectroscopic and quantum chemical studies of a new imine oxime, namely (4-nitro-phenyl)-(1-phenyl-ethylimino)-acetaldehyde oxime (nppeieoH). Spectroscopic and X-ray diffraction studies showed that nppeieoH is hydrolyzed in aqueous solution, forming nitroisonitrosoacetophenone (ninap) and the hydrolysis product binds to Pd(II) to yield [Pd(nppeieo)(ninap)]. The mechanism of the hydrolysis reaction has been theoretically investigated in detail, using density functional theory (DFT) with the B3LYP method. The vibrational and the electronic spectra of nppeieoH and its Pd(II) complex, the HOMO and LUMO analysis, Mulliken atomic charges and molecular electrostatic potential were also performed. The predicted nonlinear optical properties of both compounds are higher than those of urea.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Synthesis, Spectroscopic, Structural and Quantum Chemical Studies of a New Imine Oxime and Its Palladium(II) Complex: Hydrolysis Mechanism

2016

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“…The reactivity of the oxime group and its metal coordination capability have been studied experimentally and well documented in the literature . Isomerization reaction mechanisms and spectroscopic studies of some oximes were also performed theoretically . Schiff bases are well‐known compounds and are commonly used in industrial and biological area as a reaction intermediate.…”

Section: Introductionmentioning

confidence: 99%

Density Functional Study of the Reaction Mechanism of Two Oxiimine Alcohol Formations and Their Novel Rearrangements

Kaya

2016

Helvetica Chimica Acta

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In this study, the reaction mechanisms of isonitrosoacetophenone (inapH) with ethanolamine (ea) and 1‐phenylethanolamine (pea) have been investigated theoretically using B3LYP/6‐311G(d,p) method to explain why the formation and unexpected rearrangement products occur or not occur. While the reaction between isonitrosoacetophenone (inapH) with ethanolamine gives oximine alcohol (Ib), the reaction of 1‐phenylethanolamine with inapH results in the formation of oximine alcohol with a different substituent (Ia) and amido alcohol (IIa), which is the unexpected rearrangement product. The rearrangement driving forces of compounds from Ia to IIa are calculated as ca. 28 and 23 kJ/mol in the gas and EtOH phases, respectively. These driving forces have been calculated ca. 46 and 45 kJ/mol for the rearrangement of compound Ib to obtain IIb in the same phases, respectively. This high driving force shows that the compound IIb cannot be obtained from rearrangement of compound Ib as described experimentally in the literature. In addition, as the DFT functionals poorly describe dispersion effects, dispersion correction for reaction heat and free‐energy barrier was estimated using the wB97X‐D/6‐311G(d,p). In general, the relative free energies of all molecules calculated from wB97XD method are lower than performed from B3LYP level. The changes of thermodynamic properties for all molecules with temperature ranging from 100 to 500 K have been obtained using the statistical thermodynamic method.

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New Insights on the Mechanism of Thermal Cleavage of Unsaturated Bicyclic Diaziridines: A DFT Study

et al. 2011

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A DFT calculations are carried out at UB3LYP/6-311＋＋G (3df, 2p) levels of theory to study electrocyclic thermal cleavage of four (R) derivatives of unsaturated bicyclic diaziridines, 1 X-R , to produce corresponding (Z) and (E) azomethine imides (2 X-Z , 2 X-E , 3 X-Z and 3 X-E ), where X＝H, Me, t-Bu and Ph. Cleavage of 1 X-R series to form the most stable 3 X-Z product, (path 2) is found the favored procedure because of delocalized negative charge on five atoms and lower steric effect in related transition state. According to IRC calculations in paths 1 and 2, C 6 -N 1 bond is cleaved before the rate determinating step (transition state). The stability of unsaturated bicyclic diaziridines and their corresponding (Z) and (E) azomethine imides is in the following order in gas phase and chloroform, tetrahydrofuran, and acetone solvents: 3 X-Z ＜3 X-E ＜2 X-Z ＜2 X-E ＜1 X-R ＜1 X-S .

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Conformational Analysis, Infrared, and Fluorescence Spectra of 1-Phenyl-1,2-propandione 1-oxime and Related Tautomers: Experimental and Theoretical Study

Cited by 13 publications

References 24 publications

Synthesis, Spectroscopic, Structural and Quantum Chemical Studies of a New Imine Oxime and Its Palladium(II) Complex: Hydrolysis Mechanism

Synthesis, Spectroscopic, Structural and Quantum Chemical Studies of a New Imine Oxime and Its Palladium(II) Complex: Hydrolysis Mechanism

Density Functional Study of the Reaction Mechanism of Two Oxiimine Alcohol Formations and Their Novel Rearrangements

New Insights on the Mechanism of Thermal Cleavage of Unsaturated Bicyclic Diaziridines: A DFT Study

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