Detailed analytical studies of 1,2,4-triazole derivatized quinoline

Shilpa Mallappa Somagond; Manjunath Ningappa Wari; Saba Kauser Jaweed Shaikh; Sanjeev Ramchandra Inamdar; Madan Kumar Shankar; Dasappa Jagadeesh Prasad; Ravindra Ramappa Kamble

doi:10.5155/eurjchem.10.4.281-294.1844

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Published: Dec 31, 2019

DOI: https://doi.org/10.5155/eurjchem.10.4.281-294.1844

Keywords:

UV absorption, Hirshfeld surface, Cyclic voltammetry, Single crystal structure, Natural bond orbital (NBO), Time Dependent-Density Functional Theory

Section

Research Article

Issue

Vol. 10 No. 4 (2019): December 2019

Dates

Received 2019-03-07
Accepted 2019-07-30
Published 2019-12-31

Shilpa Mallappa Somagond

Department of Chemistry, Karnatak University, Dharwad, Karnataka 580003, India

http://orcid.org/0000-0002-0481-3426

Manjunath Ningappa Wari

Department of Physics, Karnatak University Dharwad, Karnataka 580003, India

http://orcid.org/0000-0003-0342-1284

Saba Kauser Jaweed Shaikh

Department of Chemistry, Karnatak University, Dharwad, Karnataka 580003, India

http://orcid.org/0000-0001-8839-9498

Sanjeev Ramchandra Inamdar

Department of Physics, Karnatak University Dharwad, Karnataka 580003, India

http://orcid.org/0000-0003-3398-4897

Madan Kumar Shankar

Department of Science and Technology, PURSE Laboratory, Mangalore University, Mangalagangothri, Karnataka 574199, India

http://orcid.org/0000-0002-7944-1081

Dasappa Jagadeesh Prasad

Department of Chemistry, Mangalore University, Konaje, Mangalore, Karnataka 574199, India

http://orcid.org/0000-0003-1333-028X

Ravindra Ramappa Kamble

Department of Chemistry, Karnatak University, Dharwad, Karnataka 580003, India

http://orcid.org/0000-0002-0384-655X

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 (R_int = 0.0545, R_sigma = 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.

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Somagond, S. M.; Wari, M. N.; Shaikh, S. K. J.; Inamdar, S. R.; Shankar, M. K.; Prasad, D. J.; Kamble, R. R. Detailed Analytical Studies of 1,2,4-Triazole Derivatized Quinoline. Eur. J. Chem. 2019, 10, 281-294.

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Supporting Agencies

UGC UPE FAR-I “Antitumor activity, An Integrated Approach” vide F. No. 14-3/2012 (NS/PE), University Grants commission (UGC), New Delhi, India.

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