Spectral studies of 2-pyrazoline derivatives: Structural elucidation through single crystal XRD and DFT calculations

Chinnaraja, D.; Rajalakshmi, R.; Srinivasan, T.; Velmurugan, D.; Jayabharathi, Jayaraman

doi:10.1016/j.saa.2013.12.032

Cited by 4 publications

(12 citation statements)

References 9 publications

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“…The reaction seemed to be started by first addition of active hydrogen of 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one to the ethylenic double bond of compound i. Ammonia was added to the nitrile group in ii to give iii which looses a molecule of water to give iv, which in turn was converted to the final product by auto-oxidation. The IR spectrum of compounds (1)(2)(3)(4)(5) shows the characteristic band at 3412-3442 cm −1 due to presence -NH 2 group and at 2218-2242 cm −1 attributed to the CN group. IR spectra shows sharp peek at 1234-1245 cm −1 due presence of C=N stretch which is conform to formation of quinoline.…”

Section: Resultsmentioning

confidence: 99%

“…3a, 4, 5, 6 and 7a, polarity of solvent has a little effect on the absorption maxima. All the compounds (1-5) are red-shifts with increasing solvent polarity (dye1 shifted 17 nm, dye 2 shifted 12 nm, dye 3 shifted 15 nm, dye 4 shifted 12 and dye 5 sifted 12 nm on going from n-Hexane to DMSO) indicating some polar character of isoquinoline dues (1)(2)(3)(4)(5) in the ground state. These features indicate a strongly allowed π-π* transition with charge transfer characters.…”

Section: Resultsmentioning

confidence: 99%

“…General Method for the Synthesis of Benzoquinoline Derivatives (1)(2)(3)(4)(5) A one-pot mixture of the appropriate aldehyde (0.011 mol), 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one (2 g, 0.011 mol), malononitrile (0.74 g, 0.011 mol) and ammonium acetate (6.78 g, 0.088 mol) in absolute ethanol (25 mL) was refluxed for 6 h [22]. The reaction mixture was allowed to cool, and the resulting precipitate was filtered, washed with water, dried and recrystallized from ethanol and chloroform.…”

Section: Apparatusmentioning

confidence: 99%

“…Nitrogen containing heterocyclic compounds such as pyrazoline, pyrazole qnoxaline quinoline, pyrimidene are compounds that have been studied for a considerable period of time for their biological properties [1]. Quinoline derivatives are one of the most applicable compounds in the filed of the medical chemistry [2].…”

Section: Introductionmentioning

confidence: 99%

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One Pot Synthesis, Photophysical and X-ray Studies of Novel Highly Fluorescent Isoquinoline Derivatives with Higher Antibacterial Efficacy Based on the In-vitro and Density Functional Theory

et al. 2015

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Series of cyano substituted isoquinoline dyes were synthesized by one-pot multicomponent reactions (MCRs) of aldehydes, malononitrile, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one and ammonium acetate. Results obtained from spectroscopic (FT-IR, (1)H-NMR, (13)C-NMR, EI-MS) and elemental analysis of synthesized compounds was in agreement with their chemical structures. Structure of the compound was further conformed by X-ray crystallographic. UV-vis and fluorescence spectroscopy measurements provided that all compounds are good absorbent and fluorescent. Fluorescence polarity study demonstrated that these compounds were sensitive to the polarity of the microenvironment provided by different solvents. In addition, spectroscopic and physicochemical parameters, including electronic absorption, extenction coefficient, Stokes shift, oscillator strength transition dipole moment and fluorescence quantum yield were investigated in order to explore the analytical potential of synthesized compounds. The anti-bacterial activity of these compounds were first studied in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria. The minimum inhibitory concentration was then determined with the reference of standard drug chloramphenicol. The results displayed that compound 3 was better inhibitors of both types of the bacteria (Gram-positive and Gram-negative) than chloramphenicol. Furthermore, quantum chemistry calculations using DFT/6-31-G* level of theory confirm the results. Dipole moment and frontier molecular orbitals were also investigated.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Apparatusmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

One Pot Synthesis, Photophysical and X-ray Studies of Novel Highly Fluorescent Isoquinoline Derivatives with Higher Antibacterial Efficacy Based on the In-vitro and Density Functional Theory

et al. 2015

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“…Moreover, the synthesis of fluorophores with desirable properties based on a pyrazoline skeleton is of considerable interest in fluorescent materials research [5][6][7][8]. A lot of work has been focused on the synthesis, crystal structure, optical properties and quantum chemical calculations of novel pyrazoline derivatives [9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Study on the Reactivity of Amino Acid Chemosensor, NPFNP, with Ethanol: Structural Elucidation through Single Crystal XRD and DFT Calculations

Varghese

Al‐Busafi

Suliman

et al. 2017

SQU Journal for Science

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ABSTRACT:A novel ethoxy derivative of an amino acid chemosensor, 3-naphthyl-1-phenyl-5-(2ʹ-fluoro-5ʹ-nitrophenyl)-2-pyrazoline (NPFNP), has been synthesized and characterized by different spectroscopic methods. A single crystal of the ethoxy derivative, 3-naphthyl-1-phenyl-5-(2ʹ-ethoxy-5ʹ-nitrophenyl)-2-pyrazoline NPENP, has been obtained and characterized. The structure holds interest as it carries biologically active pyrazoline as a central ring attaching to electron donating and withdrawing substituents. The major motivation for this work was to gain detailed insight into the structural parameters of this compound for investigating the influence of crystal packing and geometrical dimensions on optical properties. Time-dependent DFT calculations have been employed for comparing the XRD data with theoretical parameters. The results show that the DFT method at B3LYP/6-31G level can well reproduce the structure of the title compound.Keywords: Pyrazoline; UV absorption; Crystal structure; Chemosensor; TD-DFT. ‫األمينيه‬ ‫األحماض‬ ‫كاشف‬ ‫تفاعل‬ ‫دراسة‬

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Comparative DFT Computational Studies with Experimental Investigations for Novel Synthesized Fluorescent Pyrazoline Derivatives

Salim¹,

Girgis²,

Basta³

et al. 2018

J Fluoresc

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A novel series of pyrazoline derivatives were synthesized and their spectral properties were characterized via FT-IR, H, andC NMR. The electronic transitions and fluorescence properties were tracked via UV-Vis and emission spectrometry. The density functional theory (DFT) calculations have been also computed to get spot onto the geometry, electronic transitions and spectroscopic properties theoretically that has been compared with the encountered experimental ones. Moreover, the dipole moment, optimized energy, HOMO - LUMO energies and band gaps were calculated for novel candidates pyrazoline derivatives with highly fluorescence quantum yield.

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Spectral studies of 2-pyrazoline derivatives: Structural elucidation through single crystal XRD and DFT calculations

Cited by 4 publications

References 9 publications

One Pot Synthesis, Photophysical and X-ray Studies of Novel Highly Fluorescent Isoquinoline Derivatives with Higher Antibacterial Efficacy Based on the In-vitro and Density Functional Theory

One Pot Synthesis, Photophysical and X-ray Studies of Novel Highly Fluorescent Isoquinoline Derivatives with Higher Antibacterial Efficacy Based on the In-vitro and Density Functional Theory

Study on the Reactivity of Amino Acid Chemosensor, NPFNP, with Ethanol: Structural Elucidation through Single Crystal XRD and DFT Calculations

Comparative DFT Computational Studies with Experimental Investigations for Novel Synthesized Fluorescent Pyrazoline Derivatives

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