X-ray, DFT, FTIR and NMR structural study of 2,3-dihydro-2-(R-phenylacylidene)-1,3,3-trimethyl-1H-indole

Vázquez‐Vuelvas, Oscar F.; Hernández-Madrigal, Julia V.; Gaviño, Rubén; Tlenkopatchev, Mikhail A.; Morales‐Morales, David; Germán-Acacio, Juan Manuel; Gómez‐Sandoval, Zeferino; Garcías-Morales, Cesar; Ariza‐Castolo, Armando; Pineda-Contreras, Armando

doi:10.1016/j.molstruc.2010.12.001

Cited by 21 publications

(5 citation statements)

References 31 publications

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“…The ν(CN) band was found at 2071 cm −1 and is indicative of nitrogen coordination in complex 1 rather than sulphur coordination to Co(II) ion (terminal N-bonded) [32]. Bands related to the phen ligand were observed at 1638, 1592, 1541 and 1511 cm −1 , as reported by others [33,34]. Similar bands were found at lower frequencies in free ligand.…”

Section: Ft-ir Spectrasupporting

confidence: 75%

Synthesis, Crystal Structures and Magnetic Properties of Mononuclear High-Spin Cobalt(II) Complex

Muddassir

Song

2020

Crystals

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A new four-coordinated high-spin Co(II) complex was synthesized through the reactions of Co(NSC)2 with bathocuproine, by the diffusion method, resulting in an infinite one-dimension chain. Both static and dynamic magnetic properties were measured. The magnetic properties investigation shows that the single CoII ion properties dominate the magnetic behavior in the complex. Despite the presence of a four-coordinated single CoII ion, no SMM properties were exhibited by the complex.

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Section: Ft-ir Spectrasupporting

confidence: 75%

Synthesis, Crystal Structures and Magnetic Properties of Mononuclear High-Spin Cobalt(II) Complex

Muddassir

Song

2020

Crystals

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“…Among these bonds, N–CO is found to have the lowest values of 1.406 Å in 8 and 9 , which is a direct consequence of the electron‐withdrawing tendency of the electronegative oxygen atom. The C1–N28 bond distance (1.424 Å) in 8 and C2–N13 bond distance (1.423 Å) in 9 are consistent with the X‐ray structure of indole derivatives reported earlier . However, in indole, this bond distance is shorter, 1.37 Å, indicating that substituent has an impact on the geometry of the indole moiety .…”

Section: Resultssupporting

confidence: 88%

Palladium‐catalyzed cyclization of 2‐alkynyl‐N‐ethanoyl anilines to indoles: synthesis, structural, spectroscopic, and mechanistic study

Hoque

Halim²,

Sarwar

et al. 2015

J of Physical Organic Chem

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This study reports a facial regio‐selective synthesis of 2‐alkyl‐N‐ethanoyl indoles from substituted‐N‐ethanoyl anilines employing palladium (II) chloride, which acts as a cyclization catalyst. The mechanistic trait of palladium‐based cyclization is also explored by employing density functional theory. In a two‐step mechanism, the palladium, which attaches to the ethylene carbons, promotes the proton transfer and cyclization. The gas‐phase barrier height of the first transition state is 37 kcal/mol, indicating the rate‐determining step of this reaction. Incorporating acetonitrile through the solvation model on density solvation model reduces the barrier height to 31 kcal/mol. In the presence of solvent, the electron‐releasing (–CH3) group has a greater influence on the reduction of the barrier height compared with the electron‐withdrawing group (–Cl). These results further confirm that solvent plays an important role on palladium‐catalyzed proton transfer and cyclization. For unveiling structural, spectroscopic, and photophysical properties, experimental and computational studies are also performed. Thermodynamic analysis discloses that these reactions are exothermic. The highest occupied molecular orbitallowest unoccupied molecular orbital gap (4.9–5.0 eV) confirms that these compounds are more chemically reactive than indole. The calculated UV–Vis spectra by time‐dependent density functional theory exhibit strong peaks at 290, 246, and 232 nm, in good agreement with the experimental results. Moreover, experimental and computed 1H and 13C NMR chemical shifts of the indole derivatives are well correlated. Copyright © 2015 John Wiley & Sons, Ltd.

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“…Quantum chemical calculations are considered powerful tools to verify spectral data including the prediction of 1 H and 13 C NMR chemical shifts [14][15][16], UV-Visible absorption bands [17][18][19] and X-ray structure parameters [20,21]. Reported studies proved that to predict the excited states of some natural compounds, the use of B3LYP and PBE0 hybrid functionals are appropriate to estimate the excited state energies [22][23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, quantum chemical calculations and anticancer activity of a Schiff base NNOO chelate ligand and Pd(II) complex

et al. 2020

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This paper reports the synthesis, characterization, anticancer screening and quantum chemical calculation of a tetradentate Schiff base 2,2'-((1E,1'E)-((2,2-dimethylpropane-1,3-diyl)bis-(azanylylidene))bis(methanylylidene))bis(4-fluorophenol) (L2F) and its Pd (II) complex (PdL2F). The compounds were characterized via UV-Visible, NMR, IR spectroscopy and single crystal x-ray diffraction. Density Functional Theory (DFT) and time-dependent DFT calculations in gas and solvent phases were carried out using B3LYP, B3P86, CAM-B3LYP and PBE0 hybrid functionals combined with LanL2DZ basis set. Complexation of L2F to form PdL2F was observed to cause a bathochromic shift of the maximum absorption bands of nπ* from 327 to 410 nm; an upfield shift for δ (HC = N) from 8.30 to 7.96 ppm and a decreased wavenumber for ν(C = N) from 1637 to 1616 cm-1. Overall, the UV-Vis, NMR and IR spectral data are relatively well reproduced through DFT and TD-DFT methods. L2F and PdL2F showed IC 50 of 90.00 and 4.10 μg/mL, respectively, against human colorectal carcinoma (HCT116) cell lines, signifying increased anticancer activity upon complexation with Pd (II).

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X-ray, DFT, FTIR and NMR structural study of 2,3-dihydro-2-(R-phenylacylidene)-1,3,3-trimethyl-1H-indole

Cited by 21 publications

References 31 publications

Synthesis, Crystal Structures and Magnetic Properties of Mononuclear High-Spin Cobalt(II) Complex

Synthesis, Crystal Structures and Magnetic Properties of Mononuclear High-Spin Cobalt(II) Complex

Palladium‐catalyzed cyclization of 2‐alkynyl‐N‐ethanoyl anilines to indoles: synthesis, structural, spectroscopic, and mechanistic study

Synthesis, characterization, quantum chemical calculations and anticancer activity of a Schiff base NNOO chelate ligand and Pd(II) complex

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