Synthesis, crystal structure, spectral analysis, dft studies and antimicrobial activity of ethyl 6-(4-(Ethoxycarbonyl)-1h-1,2,3-triazol-1-yl)pyridine-3-carboxylate. | [Journal of Chemical Society of Pakistan • 2017]

Author(s):

1. Muhammad Naeem Ahmed: Department of Chemistry, The University of Azad Jammu and Kashmir,Muzaffarabad,Pakistan

2. Khawaja Ansar Yasin: Department of Chemistry, The University of Azad Jammu and Kashmir,Muzaffarabad,Pakistan

3. Raja Ansar Hussain Khan: Department of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad, Pakistan.

4. Tariq Mahmood: Department of Chemistry, COMSATS Institute of Information Technology,University Road, Tobe Camp, Abbottabad,Pakistan

5. Khurshid Ayub: Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, Abbottabad, Pakistan

6. Dilshad Malik: Department of Chemistry, University of Zululand, Private bag X1001, Kwa-Dlangezwa, South Africa.

7. Muhammad Hafeez: Department of Chemistry, The University of Azad Jammu and Kashmir, Muzaffaraba, Pakistan.

8. Abdul Majeed Khan: Research Laboratory of Bioenergy, Department of Chemistry, Federal Urdu University, Gulshan-e-Iqbal Campus, University Road, Karachi, Pakistan.

9. M. Nawaz Tahir: Department of Physics, University of Sargodha, Pakistan.

Abstract:

Ethyl-6-(4-(ethoxycarbonyl)-1H-1,2,3-triazol-1-yl)pyridine-3-carboxylate (1), was synthesized via click reaction between ethyl tetrazolo[1,5-a]pyridine-6-carboxylate and ethyl propiolate in tetrahydrofuran (THF) in the presence of catalytic amount of a copper acetate. The structure was confirmed by single-crystal X-ray diffraction, NMR, FT-IR and MS. The compound crystallizes in the triclinic system, space group P¯1 with a = 4.9122 (5), b = s9.5891 (11), c = 15.4851 (18)Å, a = 92.371 (5), ß = 90.015 (4), ? = 101.722 (5) Z = 2 and V (Å3) = 713.55 (14). Packing diagram indicates that there is dimeric interaction between two units via N(2)···H(7). The crystal structure of the title compound 1 is stabilized by several nonboding interactions. Space filling model also revealed C-H···p and the p-p interactions in the molecule. Theoretical investigations were executed by using the Gaussian 09 software to enable comparison with X-ray structure as well as spectroscopic results, and to further probe the structural properties. The molecular electrostatic potential (MEP) analysis gave the idea about chemical reactivity and the Mulliken charge analysis gave quantitative estimate of the charges on the atoms. Frontier molecular orbitals analysis (electronic properties) was used to find the energy gap between the HOMO and the LUMO. The target compound was screened against three different bacterial strains like S. typhimurium, M. luteus and B. bronchiseptica as well as three different fungal strains i.e Aspergilus niger, Mucor specie and Aspergilus flavus. Moderate activities have been displayed by the target compound against tested strains.

Page(s): 640-649

DOI: DOI not available

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 39, Issue: 4, Year: 2017

Keywords:

XRay , click chemistry , 4Disubstituted triazole , Density functional theory DFT

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