Detailed analytical studies of 1,2,4-triazole derivatized quinoline
Open Access
- 31 December 2019
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 10 (4), 281-294
- https://doi.org/10.5155/eurjchem.10.4.281-294.1844
Abstract
The present study describes, the X-ray single crystal analysis of 4-((2-chloro-6-methoxyquinolin-3-yl)methyl)-2-phenyl-2H-1,2,4-triazol-3(4H)-one (TMQ). The crystal data for C19H15ClN4O2: monoclinic, space group P21/n (no. 14), a = 7.3314(15) Å, b = 12.459(3) Å, c = 18.948(4) Å, β = 98.322(9)°, V = 1712.5(6) Å3, Z = 4, T = 296.15 K, μ(MoKα) = 0.245 mm-1, Dcalc = 1.423 g/cm3, 5082 reflections measured (3.926° ≤ 2Θ ≤ 38.556°), 1428 unique (Rint = 0.0545, Rsigma = 0.0574) which were used in all calculations. The final R1 was 0.0423 (I >2σ(I)) and wR2 was 0.1145 (all data). The Density functional theory optimized molecular geometries in TMQ agree closely with those obtained from crystallographic studies. The Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energy levels and energy gap were calculated by experimental (UV absorption & Cyclic voltammetry) and theoretical studies in two different solvents. The natural bond orbital analysis was performed to understand the molecular interaction on the basis of stability of molecule arising from hyper-conjugative interaction and charge delocalization. Hirshfeld surface and their related fingerprint plots enabled the identification of significant intermolecular interaction. The molecular electrostatic potential analysis provides the visual image of the chemically active sites and comparable reaction of atoms.Keywords
This publication has 40 references indexed in Scilit:
- Tautomerism aspect of thione-thiol combined with spectral investigation of some 4-amino-5-methyl-1,2,4-triazole-3-thione Schiff's basesJournal of Molecular Structure, 2017
- Asymmetric Induction in Hydroacylation by Cooperative Iminium Ion–Transition-Metal CatalysisOrganic Letters, 2016
- An efficient quinoline-based fluorescence sensor for zinc(II) and its application in live-cell imagingSensors and Actuators B: Chemical, 2016
- Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activityOrganic & Biomolecular Chemistry, 2016
- Synergistic anti-malarial action of cryptolepine and artemisininsMalaria Journal, 2016
- The Self‐Assembly of Anticancer Camptothecin–Dipeptide Nanotubes: A Minimalistic and High Drug Loading Approach to Increased EfficacyChemistry – A European Journal, 2014
- Pharmacophore modeling, 3DQSAR, and docking-based design of polysubstituted quinolines derivatives as inhibitors of phosphodiesterase 4, and preliminary evaluation of their anti-asthmatic potentialMedicinal Chemistry Research, 2014
- Quinoline-Based AntifungalsCurrent Medicinal Chemistry, 2010
- An Effective Fluorescent Chemosensor for Mercury IonsJournal of the American Chemical Society, 2000
- In vitro activity of Bay 09867, a new quinoline derivative, compared with those of other antimicrobial agentsAntimicrobial Agents and Chemotherapy, 1983