Overcoming the ring tension: computational approaches to stereochemical assignments and geometrical insights in small heterocycles

In this study, we evaluate the performance of the DP4+ and MM-DP4+ methods on molecules featuring small heterocyclic rings. A dataset of 71 molecules containing three- and four-membered heterocycles, known for their stereochemical assignment challenges, was analyzed. We compared molecular geometries...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Luciano, Ezequiel R., Amichetti, Milagros, Sarotti, Ariel M., Zanardi, María M.
Formato: Artículo
Lenguaje:Inglés
Publicado: The Royal Society of Chemistry 2025
Materias:
QUIMICA COMPUTACIONAL
COMPUESTOS HETEROCICLICOS
ESTRUCTURA MOLECULAR
Acceso en línea:https://repositorio.uca.edu.ar/handle/123456789/19994
Aporte de:
Repositorio Institucional de la Universidad Católica Argentina (UCA) de Universidad Católica Argentina
id I33-R139-123456789-19994
record_format dspace
spelling I33-R139-123456789-199942025-07-04T05:02:06Z Overcoming the ring tension: computational approaches to stereochemical assignments and geometrical insights in small heterocycles Luciano, Ezequiel R. Amichetti, Milagros Sarotti, Ariel M. Zanardi, María M. QUIMICA COMPUTACIONAL COMPUESTOS HETEROCICLICOS ESTRUCTURA MOLECULAR In this study, we evaluate the performance of the DP4+ and MM-DP4+ methods on molecules featuring small heterocyclic rings. A dataset of 71 molecules containing three- and four-membered heterocycles, known for their stereochemical assignment challenges, was analyzed. We compared molecular geometries optimized at different computational levels, including MMFF and B3LYP/6-31G*, to assess deviations in key geometric parameters relative to the heterocycle structures. Furthermore, the geometric properties of these molecules were investigated using various force fields to evaluate their differences. Our aim was to assess the reliability of B3LYP/6-31G* in comparison with more accurate methods and to elucidate how different force fields influence in geometric precision. 2025-07-03T17:31:17Z 2025-07-03T17:31:17Z 2025 Artículo https://repositorio.uca.edu.ar/handle/123456789/19994 10.1039/d4ob01959h eng Atribución-NoComercial-CompartirIgual 4.0 Internacional http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf The Royal Society of Chemistry Organic & Biomolecular Chemistry. 10, 2025.
institution Universidad Católica Argentina
institution_str I-33
repository_str R-139
collection Repositorio Institucional de la Universidad Católica Argentina (UCA)
language Inglés
topic QUIMICA COMPUTACIONAL
COMPUESTOS HETEROCICLICOS
ESTRUCTURA MOLECULAR
spellingShingle QUIMICA COMPUTACIONAL
COMPUESTOS HETEROCICLICOS
ESTRUCTURA MOLECULAR
Luciano, Ezequiel R.
Amichetti, Milagros
Sarotti, Ariel M.
Zanardi, María M.
Overcoming the ring tension: computational approaches to stereochemical assignments and geometrical insights in small heterocycles
topic_facet QUIMICA COMPUTACIONAL
COMPUESTOS HETEROCICLICOS
ESTRUCTURA MOLECULAR
description In this study, we evaluate the performance of the DP4+ and MM-DP4+ methods on molecules featuring small heterocyclic rings. A dataset of 71 molecules containing three- and four-membered heterocycles, known for their stereochemical assignment challenges, was analyzed. We compared molecular geometries optimized at different computational levels, including MMFF and B3LYP/6-31G*, to assess deviations in key geometric parameters relative to the heterocycle structures. Furthermore, the geometric properties of these molecules were investigated using various force fields to evaluate their differences. Our aim was to assess the reliability of B3LYP/6-31G* in comparison with more accurate methods and to elucidate how different force fields influence in geometric precision.
format Artículo
author Luciano, Ezequiel R.
Amichetti, Milagros
Sarotti, Ariel M.
Zanardi, María M.
author_facet Luciano, Ezequiel R.
Amichetti, Milagros
Sarotti, Ariel M.
Zanardi, María M.
author_sort Luciano, Ezequiel R.
title Overcoming the ring tension: computational approaches to stereochemical assignments and geometrical insights in small heterocycles
title_short Overcoming the ring tension: computational approaches to stereochemical assignments and geometrical insights in small heterocycles
title_full Overcoming the ring tension: computational approaches to stereochemical assignments and geometrical insights in small heterocycles
title_fullStr Overcoming the ring tension: computational approaches to stereochemical assignments and geometrical insights in small heterocycles
title_full_unstemmed Overcoming the ring tension: computational approaches to stereochemical assignments and geometrical insights in small heterocycles
title_sort overcoming the ring tension: computational approaches to stereochemical assignments and geometrical insights in small heterocycles
publisher The Royal Society of Chemistry
publishDate 2025
url https://repositorio.uca.edu.ar/handle/123456789/19994
work_keys_str_mv AT lucianoezequielr overcomingtheringtensioncomputationalapproachestostereochemicalassignmentsandgeometricalinsightsinsmallheterocycles
AT amichettimilagros overcomingtheringtensioncomputationalapproachestostereochemicalassignmentsandgeometricalinsightsinsmallheterocycles
AT sarottiarielm overcomingtheringtensioncomputationalapproachestostereochemicalassignmentsandgeometricalinsightsinsmallheterocycles
AT zanardimariam overcomingtheringtensioncomputationalapproachestostereochemicalassignmentsandgeometricalinsightsinsmallheterocycles
_version_ 1845297941725577216

Ejemplares similares