Home Physical Sciences A computational study of the conformational stability, vibrational spectra, and thermochemical properties of 2,6-dichlorobenzamide, 2-(trifluoromethyl)benzamide, 2-(trifluoromethyl)benzoic acid, and 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid
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A computational study of the conformational stability, vibrational spectra, and thermochemical properties of 2,6-dichlorobenzamide, 2-(trifluoromethyl)benzamide, 2-(trifluoromethyl)benzoic acid, and 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid

  • Wilfred Espinosa Manrique ORCID logo , María Paula Badenes ORCID logo EMAIL logo and María Eugenia Tucceri ORCID logo EMAIL logo
Published/Copyright: September 18, 2023
Zeitschrift für Physikalische Chemie
From the journal Zeitschrift für Physikalische Chemie Volume 237 Issue 10

Abstract

2,6-Dichlorobenzamide (BAM), 2-(trifluoromethyl)benzamide (TBAM), 2-(trifluoromethyl)benzoic acid (TBA), and 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid (PCA) are degradation by-products of fluopicolide and fluopyram fungicides. In this work, a detailed theoretical study of their different molecular, spectroscopic and thermochemical properties was carried out with different formulations of the density functional theory and high-level model chemistries. The mean values of −146.0 ± 6.3, −763.2 ± 6.3, −949.0 ± 6.3, and −919.4 ± 6.3 kJ mol−1 for the standard enthalpies of formation of BAM, TBAM, TBA and PCA, respectively, were derived for the first time at the G3MP2//DFT and G4MP2//DFT levels of theory (DFT = B3LYP, BMK, and B98). Additionally, a good agreement between formation enthalpies derived from isodesmic reaction approach and from Benson’s group additivity method was obtained.

Keywords: fluorinated pesticide; chlorinated pesticide; fungicide; degradation by-products; quantum-chemical calculations; 2,6-dichlorobenzamide, 2-(trifluoromethyl)benzamide, 2-(trifluoromethyl)benzoic acid, 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid
Corresponding authors: María Paula Badenes and María Eugenia Tucceri, Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, CCT La Plata-CONICET, Casilla de Correo 16, Sucursal 4, (1900) La Plata, Argentina, E-mail: (M.P. Badenes), (M.E. Tucceri)

  1. Research ethics: Not applicable.

  2. Author contributions: The authors have accepted responsibility for the entire content of this manuscript and approved its submission. Contribution of each author: Wilfred Espinosa Manrique: Theoretical calculations. Formal analysis. María Paula Badenes: Conceptualization. Formal analysis. Writing – Original Draft. Writing-Review and Editing. Project administration. María Eugenia Tucceri: Conceptualization. Formal analysis. Writing – Original Draft. Writing-Review and Editing. Project administration.

  3. Competing interests: The authors state no conflict of interest.

  4. Research funding: This work was supported by the Universidad Nacional de La Plata (11/X842, 11/X919); the Consejo Nacional de Investigaciones Científicas y Tócnicas CONICET (PUE 22920170100100CO); and the Agencia Nacional de Promoción Científica y Tecnológica (PICT 2018-2523, PICT 2018-3738). W. E. M. thanks CONICET for his doctoral fellowship.

  5. Data availability: The raw data can be obtained on request from the corresponding author.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/zpch-2023-0204).

Received: 2022-12-29
Accepted: 2023-08-21
Published Online: 2023-09-18
Published in Print: 2023-10-26

© 2023 Walter de Gruyter GmbH, Berlin/Boston

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https://doi.org/10.1515/zpch-2023-0204
Keywords for this article
fluorinated pesticide; chlorinated pesticide; fungicide; degradation by-products; quantum-chemical calculations; 2,6-dichlorobenzamide, 2-(trifluoromethyl)benzamide, 2-(trifluoromethyl)benzoic acid, 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid

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