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Communication

Activation–Deactivation of Inter-Peptide Bond in Fluoro-N-(2-hydroxy-5-methyl phenyl)benzamide Isomers, Induced by the Position of the Halogen Atom in the Benzene Ring

1
Department of Chemistry, Universidad del Valle, Santiago de Cali A.A. 25360, Colombia
2
Laboratorio de Química Supramolecular y Fotobiología, Departamento de Química Física, Escuela de Química, Facultad de Química y de Farmacia, Pontificia Universidad Católica de Chile, Vicuña Mackenna, Macul, Santiago 4860, Chile
3
Instituto de Física, Universidade Federal do Rio de Janeiro, Rio de Janeiro CEP. 21941-909, Brazil
4
Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos CEP. 13566-590, Brazil
5
WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK
*
Author to whom correspondence should be addressed.
Academic Editor: René T. Boeré
Molbank 2022, 2022(3), M1416; https://doi.org/10.3390/M1416
Received: 25 June 2022 / Revised: 22 July 2022 / Accepted: 27 July 2022 / Published: 29 July 2022
(This article belongs to the Section Structure Determination)
The synthesis and XRD characterization at 295 K of three isomers, X-fluoro-N-(2-hydroxy-5-methyl phenyl) benzamide: (o-FPhB), (m-FPhB), and (p-FPhB), are presented. o-FPhB and m-FPhB show high structural affinity concerning molecular and packing structures. The planarity of the C1-C7(O1)-N1-C8 peptide bond in o-FPhB, and m-FPhB confers high stability, favoring its tendency to acquire a resonant structure in the peptide segment and in the molecule. For p-FPhB, a stereochemical gate opens, leading to the activation of N-H∙∙∙∙O interpeptide bonds, defining its supramolecular properties. Active participation of the halogen in the assembly of the structures is observed, forming intramolecular rings and molecule chains during crystal growth. The o-FPhB and m-FPhB form parallel sheets that develop hydrogen C-H···Cg, halogen C-F···Cg, or C=O···Cg interactions. Theoretical evaluations of the properties performed by the DFT/B3LYP/(6-311G(d,p) showed good agreement with the experimental values. The IR analysis reaffirms the presence of N-H, C=O, O-H, C-F, and C-H. In the UV-Vis, an increase in the energetic stability, O···H interactions, and electrostatic potential in the NH region reaffirm the disposition of p-FPhB for the formation of the N-H···O interpeptide bond. A molecular docking on the benzamides involving protein receptors showed similar behavior for all three isomers. View Full-Text
Keywords: crystal structure; fluorobenzamide; Hirshfeld surface; MEP; molecular docking crystal structure; fluorobenzamide; Hirshfeld surface; MEP; molecular docking
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MDPI and ACS Style

Moreno-Fuquen, R.; Mariño-Ocampo, N.; Tenorio, J.C.; Ellena, J.; Kennedy, A.R. Activation–Deactivation of Inter-Peptide Bond in Fluoro-N-(2-hydroxy-5-methyl phenyl)benzamide Isomers, Induced by the Position of the Halogen Atom in the Benzene Ring. Molbank 2022, 2022, M1416. https://doi.org/10.3390/M1416

AMA Style

Moreno-Fuquen R, Mariño-Ocampo N, Tenorio JC, Ellena J, Kennedy AR. Activation–Deactivation of Inter-Peptide Bond in Fluoro-N-(2-hydroxy-5-methyl phenyl)benzamide Isomers, Induced by the Position of the Halogen Atom in the Benzene Ring. Molbank. 2022; 2022(3):M1416. https://doi.org/10.3390/M1416

Chicago/Turabian Style

Moreno-Fuquen, Rodolfo, Nory Mariño-Ocampo, Juan Carlos Tenorio, Javier Ellena, and Alan R. Kennedy. 2022. "Activation–Deactivation of Inter-Peptide Bond in Fluoro-N-(2-hydroxy-5-methyl phenyl)benzamide Isomers, Induced by the Position of the Halogen Atom in the Benzene Ring" Molbank 2022, no. 3: M1416. https://doi.org/10.3390/M1416

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