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Analysis of institutional authors

Bernús, MiguelAuthorGuasch, MarcAuthorBesora, MariaCorresponding AuthorCarbo, Jorge JCorresponding AuthorBoutureira, OmarCorresponding Author

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February 26, 2025
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Article

Impact of Fluorine Pattern on Lipophilicity and Acid-Base Properties of 2-(Thiofluoroalkyl)pyridines: Insights from Experiments and Statistical Modeling

Publicated to: Journal Of Medicinal Chemistry. 68 (4): 4787-4800 - 2025-02-17 68(4), DOI: 10.1021/acs.jmedchem.4c03045

Authors:

Bernús, M; Núñez, GD; Hartley, WC; Guasch, M; Mestre, J; Besora, M; Carbó, JJ; Boutureira, O
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Affiliations

Univ Rovira i Virgili, Dept Quim Analit & Quim Organ, Tarragona 43007, Spain - Author
Univ Rovira i Virgili, Dept Quim Fis & Inorgan, Tarragona 43007, Spain - Author

Abstract

Lipophilicity and acid-base properties are two key aspects of the optimization of a compound in drug discovery. Using 19F NMR, we experimentally determined the log D 7.4 of a wide array of 2-thiofluoroalkyl (SRF) and 2-sulfonyl fluoroalkyl (SO2RF) substituted pyridines and the pK a values of their protonated counterparts. Statistical modeling based on constitutional and DFT descriptors provided further insights into the structure-property relationship, explaining the experimental observations and predicting log D 7.4 values. Our results highlight the influence of fluorination topology in SRF fragments and demonstrate the dual effect of fluorine on molecular polarity, increasing the hydrophobic surface and the polarity of the sulfur moiety. By analyzing methyl- and ethyl-derived fragments, we found a gradient in log D 7.4 values influenced by the oxidation state of the sulfur atom and fluorination pattern. Our findings emphasize the context-dependent impact of fluorination and offer insights to better understand the impact of thiofluoroalkyl chains on these physicochemical properties.
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Keywords

Ab-initioAryChemistryContinuumDensity functional theoryDerivativesFluorineHalogenationHydrophobic and hydrophilic interactionsMagnetic resonance spectroscopyModels, statisticalMolecular structureMolecular-orbital methodsMotifsNonnucleosidePyridinesThiolsTrifluoromethylthiolation

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Journal Of Medicinal Chemistry due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2025, it was in position 7/72, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Medicinal. Notably, the journal is positioned above the 90th percentile.

Independientemente del impacto esperado determinado por el canal de difusión, es importante destacar el impacto real observado de la propia aportación.

Según las diferentes agencias de indexación, el número de citas acumuladas por esta publicación hasta la fecha 2026-01-20:

  • WoS: 5
  • Scopus: 4
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Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2026-01-20:

  • The use, from an academic perspective evidenced by the Altmetric agency indicator referring to aggregations made by the personal bibliographic manager Mendeley, gives us a total of: 9.
  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 9 (PlumX).

With a more dissemination-oriented intent and targeting more general audiences, we can observe other more global scores such as:

  • The Total Score from Altmetric: 7.
  • The number of mentions on the social network X (formerly Twitter): 14 (Altmetric).

It is essential to present evidence supporting full alignment with institutional principles and guidelines on Open Science and the Conservation and Dissemination of Intellectual Heritage. A clear example of this is:

  • The work has been submitted to a journal whose editorial policy allows open Open Access publication.
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Leadership analysis of institutional authors

There is a significant leadership presence as some of the institution’s authors appear as the first or last signer, detailed as follows: First Author (Bernús Pérez, Miguel) and Last Author (Boutureira Martín, Omar).

the authors responsible for correspondence tasks have been Besora Bonet, Maria, Carbó Martin, Jorge Juan and Boutureira Martín, Omar.

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Awards linked to the item

We thank the Spanish Government-MICIU, the National Agency of Investigation-AEI/10.13039/501100011033, "ERDF A way of making Europe", and the European Union NextGenerationEU/PRTR (PID2020-120584RB-I00 and PID2023-153360NB-I00 to O.B., PID2021-128128NB-I00 to J.J.C., CNS2022-136079 to M.B., FPU Fellowship; FPU19/01969 to M.B., and FPI Fellowship; PRE2019-087804 to G.D.N.), AGAUR for 2023 INV-2 00033, 200033ID12 to W.C.H., and the Generalitat de Catalunya for the grant 2021SGR00110 to G.D.N., M.B., and J.J.C.
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