European Journal of Chemistry

Synthesis, crystal structure elucidation, Hirshfeld surface analysis, 3D energy frameworks and DFT studies of 2-(4-fluorophenoxy) acetic acid

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Published: Sep 30, 2021
DOI: https://doi.org/10.5155/eurjchem.12.3.304-313.2099
Keywords:
DFT, MEP, HOMO-LUMO, Crystal structure, Phenoxyacetic acid, Hirshfeld surface analysis
Section
Research Article
Issue
Vol. 12 No. 3 (2021): September 2021
Dates
Received 2021-01-30
Accepted 2021-08-07
Published 2021-09-30
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Akhileshwari Prabhuswamy
Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
https://orcid.org/0000-0003-0716-3542
Yasser Hussein Eissa Mohammed
Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysuru 570 006, India
https://orcid.org/0000-0003-1086-7292
Fares Hezam Al-Ostoot
Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysuru 570 006, India
https://orcid.org/0000-0003-4571-6419
Geetha Doddanahalli Venkatesh
Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
https://orcid.org/0000-0001-8628-8794
Sridhar Mandayam Anandalwar
Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
https://orcid.org/0000-0002-3065-3630
Shaukath Ara Khanum
Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysuru 570 006, India
https://orcid.org/0000-0003-1713-4489
Lokanath Neratur Krishnappagowda
Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
https://orcid.org/0000-0003-2773-2247

Abstract

The compound 2-(4-fluorophenoxy) acetic acid was synthesized by refluxing, 4-fluoro-phenol as a starting material with ethyl chloroacetate in acetone as solvent. The compound crystallizes in the monoclinic crystal system with the space group P21/c. Crystal data for C8H7FO3, a = 13.3087(17) Å, b = 4.9912(6) Å, c = 11.6018(15) Å, β = 104.171(4)°, V = 747.21(16) Å3, Z = 4, T = 293(2) K, μ(CuKα) = 1.142 mm-1, Dcalc = 1.512 g/cm3, 8759 reflections measured (13.72° ≤ 2Θ ≤ 130.62°), 1246 unique (Rint = 0.0528) which were used in all calculations. The final R1 was 0.0458 (>2sigma(I)) and wR2 was 0.1313 (all data). The structure was stabilized by C-H···O and C-H···Cg interactions. The intermolecular interactions in the crystal were studied using Hirshfeld surface analysis. 3D energy frameworks were computed to visualize the packing modes. DFT calculations were performed. The FMOs were studied to estimate the kinetic stability and reactivity of the molecule. The MEP surface was generated to investigate the charge distribution and chemical reactive sites in the molecule.


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Prabhuswamy, A.; Mohammed, Y. H. E.; Al-Ostoot, F. H.; Venkatesh, G. D.; Anandalwar, S. M.; Khanum, S. A.; Krishnappagowda, L. N. Synthesis, Crystal Structure Elucidation, Hirshfeld Surface Analysis, 3D Energy Frameworks and DFT Studies of 2-(4-Fluorophenoxy) Acetic Acid. Eur. J. Chem. 2021, 12, 304-313.

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