Vibrational spectra, molecular structure, natural bond orbital, first order hyperpolarizability, TD-DFT and thermodynamic analysis of 4-amino-3-hydroxy-1-naphthalenesulfonic acid by DFT approach

Sebastian, S.; Sylvestre, S.; Sundaraganesan, N.; Ayyapan, S.; Oudayakumar, K.; Karthikeyan, B.

doi:10.1016/j.saa.2013.01.041

Cited by 36 publications

(6 citation statements)

References 35 publications

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“…3(2), 130-149, (2014) This may be due to the conjugation with ring π system. NH 2 scissoring vibrations give rise to a band in the region 1620 ± 20 cm -1 and rocking vibration in the range 1195 ± 90 cm -1 (Sebastian et al 2013). In our study, the frequency observed at 1548 (APC) and 1608 cm -1 (MAPC) in IR spectrum were due to scissoring vibrations.…”

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confidence: 54%

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The spectroscopic investigation of 3-amino-2-pyrazinecarboxylicacid and methyl-3-amino-2-pyrazinecarboxylate - A Comparative Study

2014

J. Environ. Nanotechnol.

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The FTIR and FT-Raman spectra of 3-amino-2-pyrazine carboxylic acid (APC) and methyl-3-amino-2pyrazine carboxylate (MAPC) have been recorded in the region 4000-400 cm -1 and 3500-100 cm -1 respectively. The optimized geometry, frequency and intensity of the vibrational bands of the compounds were obtained by the density functional theory using 6-311++G(d,p) basis set. The harmonic vibrational frequencies were calculated and the scaled values have been compared with experimental FTIR and FT-Raman spectra. The observed and the calculated frequencies are found to be in good agreement. A detailed interpretation of the infrared and Raman spectra were also reported based on potential energy distribution (PED). 1 H and 13 C NMR spectra were recorded and its corresponding nuclear magnetic resonance chemical shifts of the molecule were also calculated using the gauge independent atomic orbital (GIAO) method. UV-Visible spectrum of these compounds was recorded and the electronic properties HOMO and LUMO energies were measured by TD-DFT approach. The calculated HOMO and LUMO energies show that charge transfer occurs within the molecule. Furthermore, molecular electrostatic potential was performed. Molecular stability and bond strength were investigated by applying the natural bond orbital analysis (NBO).of this structural feature is that the lone pair of electron on nitrogen atom is not associated with the ring and is available for protonation (Krishnakumar and Prabavathi, 2009).Hence, the spectroscopic investigation of 3-amino-2-pyrazine carboxylicacid (APC) and methyl-3-amino-2-pyrazine carboxylate (MAPC) have been carried out and will be helpful in understanding various structural and spectral characteristics of these compounds. EXPERIMENTAL DETAILSThe fine polycrystalline sample of APC and MAPC were obtained from Lancaster chemical company, UK, and used as such for the spectral measurements. The room temperature FTIR spectrum of the compounds were measured in the region 4000-400 cm -1 at a resolution of ±1cm -1 , using a BRUKER IFS-66V vacuum Fourier transform spectrometer equipped with a mercuryc admium telluride (MCT) detector, a KBr beam splitter and globar source. The FT-Raman spectrum was recorded on a BRUKER IFS-66V model interferometer equipped with an FRA-106 FT-Raman accessory. The spectrum was recorded in the 4000-50 cm -1 Stokes region using the 1064 nm line of a Nd :YAG laser for the excitation operating at 200mW power. The reported wave numbers are expected to be accurate within to ±1 cm -1 .

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confidence: 54%

“…The NH 2 group has two N-H stretching vibrations, such as symmetric and antisymmetric stretching modes. The NH 2 asymmetric stretching vibrations give rise to a strong band in the region 3390 ± 60 cm -1 and the symmetric NH 2 stretching is observed as weak band in the region 3210 ± 60 cm -1 (Sebastian et al 2013).…”

Section: Nh 2 Vibrations Of Apc and Mapcmentioning

confidence: 96%

The spectroscopic investigation of 3-amino-2-pyrazinecarboxylicacid and methyl-3-amino-2-pyrazinecarboxylate - A Comparative Study

2014

J. Environ. Nanotechnol.

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“…There were neither the SH stretching vibration band observable at around 2600 cm −1 nor the C═S stretching vibration band observable at 1260 cm −1 ; instead new bands were observed in the region 1100–1300 cm −1 , characteristic of the fundamental vibrational mode of the sulfonate in the crystalline state . The new bands in the region 1218–1249 cm −l were assigned tentatively to the stretching modes of SO 2 . The bands at 1025 and 1249 cm −l were attributable to symmetric and asymmetric modes, respectively, of the sulfonate in 1 .…”

Section: Resultsmentioning

confidence: 89%

Structural studies and cytotoxic activity of a new dinuclear coordination compound of palladium(II)–2,2′:6′,2″‐terpyridine with rigid dianionic 1,2,4‐triazole‐3‐sulfonate linker

Büyükekşi

Erkısa

Şengül

et al. 2018

Applied Organom Chemis

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A new dinuclear coordination compound of palladium(II), [Pd2(terpy)2(μ‐tas‐N1,N4)]SO4⋅11H2O (1), was synthesized by tethering a doubly deprotonated 1,2,4‐triazole‐3‐sulfonate (tas) linker generated in situ via oxidation of 1,2,4‐triazole‐3‐thione (tat) under the synthetic conditions. X‐ray diffraction analysis reveals that tat molecules adopt the thione form in the solid state, and are combined in infinite chains by symmetrically related classical intermolecular hydrogen bonds N1─H1⋅⋅⋅S1, N3─H3⋅⋅⋅N2 to give rise to R22(7) pattern in one‐dimensional chains along the b‐axis propagating along the a‐axis. Further short contacts through lone pairs of N2⋅⋅⋅S1 on the rings between the adjacent chains along the a‐axis lead to a two‐dimensional network structure. Compound 1 was characterized using infrared, 1H NMR and UV–visible spectroscopies, electrospray ionization mass spectrometry and X‐ray crystallography. The crystal structure determination of 1 reveals that the Pd(II) ions are coordinated with four nitrogen atoms: three from terpy and one from tas acting as an end‐to‐end (μ‐1,4) bridging ligand. The Pd(II) ions in 1 adopt a distorted square planar geometry. The anti‐growth effect of 1 was tested on colorectal cancer (HCT‐15), non‐small‐cell lung cancer (A549), prostate cancer (PC‐3) and cervical cancer (HeLa) cell lines using sulforhodamine B viability assay. The cytotoxic effect was further confirmed using adenosine triphosphate viability assay. Compound 1 shows a promising cytotoxic activity in the diverse cancer cell models in vitro (p <0.0001).

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“…The C-H in-plane bending vibrations were calculated at 1057, 1069, 1096, 1107, 1165, 1216, 1278 cm −1 , respectively based on PED results. Generally, the stretching vibrations of C-C bands occur in the range 1430-1625 cm −1 in the aromatic ring [53] . This band was observed at 1506, 1557 cm −1 in FTIR and 1509, 1560, 1582 cm −1 in FTRaman and that it was well coherent with the simulated data at 1504, 1548, 1554, 1577 and 1580 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, X-ray crystal structure, IR and Raman spectroscopic analysis, quantum chemical computational and molecular docking studies on hydrazone-pyridine compound: As an insight into the inhibitor capacity of main protease of SARS-CoV2

Topal

Zorlu

Karapınar

2021

Journal of Molecular Structure

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The characterization and synthesis of 3-chloro-2-{(2E)-2-[1-(4-chlorophenyl)ethylidene]hydrazinyl}pyridine (CCPEHP) was investigated in our study. Mass and UV-visible spectra were recorded in chloroform solvent. The CCPEHP molecule containing pyridine and chlorophenyl rings and hydrazone group crystallized in the triclinic system and P-1 space group. FTRaman and FTIR spectra were performed in the solid state. The optimized geometry of CCPEHP was computed by DFT/B3LYP method with 6-311G (d, p) and 6-31G (d, p) levels. The computed vibrational analysis, electronic absorption spectrum, electronic properties, molecular electrostatic potential, natural bond orbitals analysis and other calculated structural parameters were determined by using the DFT/B3LYP/6-31G (d, p) basis set. The correlation of fundamental modes of the compound and the complete vibrational assignments analysis were studied. The strong and weak contacts were identified by using Hirshfeld surface analysis. The molecular modeling results showed that CCPEHP structure strongly binds to COVID-19 main protease by relative binding affinity of -6.4 kcal/mol.

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Vibrational spectra, molecular structure, natural bond orbital, first order hyperpolarizability, TD-DFT and thermodynamic analysis of 4-amino-3-hydroxy-1-naphthalenesulfonic acid by DFT approach

Cited by 36 publications

References 35 publications

The spectroscopic investigation of 3-amino-2-pyrazinecarboxylicacid and methyl-3-amino-2-pyrazinecarboxylate - A Comparative Study

The spectroscopic investigation of 3-amino-2-pyrazinecarboxylicacid and methyl-3-amino-2-pyrazinecarboxylate - A Comparative Study

Structural studies and cytotoxic activity of a new dinuclear coordination compound of palladium(II)–2,2′:6′,2″‐terpyridine with rigid dianionic 1,2,4‐triazole‐3‐sulfonate linker

Synthesis, X-ray crystal structure, IR and Raman spectroscopic analysis, quantum chemical computational and molecular docking studies on hydrazone-pyridine compound: As an insight into the inhibitor capacity of main protease of SARS-CoV2

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