Revisiting the rearrangement of Dewar thiophenes

Sara Gómez; Edison Osorio; Eugenia Dzib; Rafael Islas; Albeiro Restrepo; Gabriel Merino

doi:10.3390/molecules25020284

Revisiting the rearrangement of Dewar thiophenes

Sara Gómez, Edison Osorio, Eugenia Dzib, Rafael Islas, Albeiro Restrepo, Gabriel Merino

Producción científica: Contribución a una revista › Artículo › revisión exhaustiva

10 Citas (Scopus)

Resumen

The mechanism for the walk rearrangement in Dewar thiophenes has been clarified theoretically by studying the evolution of chemical bonds along the intrinsic reaction coordinates. Substituent effects on the overall mechanism are assessed by using combinations of the ring (R = H, CF₃) and traveling (X = S, S = O, and CH₂) groups. The origins of fluxionality in the S-oxide of perfluorotetramethyl Dewar thiophene are uncovered in this work. Dewar rearrangements are chemical processes that occur with a high degree of synchronicity. These changes are directly related to the activation energy.

Idioma original	Inglés
Número de artículo	284
Publicación	Molecules
Volumen	25
N.º	2
DOI	https://doi.org/10.3390/molecules25020284
Estado	Publicada - 1 ene. 2020

Áreas temáticas de ASJC Scopus

Química analítica
Química (miscelánea)
Medicina molecular
Ciencias farmacéuticas
Descubrimiento de medicamentos
Química física y teórica
Química orgánica

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abstract = "The mechanism for the walk rearrangement in Dewar thiophenes has been clarified theoretically by studying the evolution of chemical bonds along the intrinsic reaction coordinates. Substituent effects on the overall mechanism are assessed by using combinations of the ring (R = H, CF3) and traveling (X = S, S = O, and CH2) groups. The origins of fluxionality in the S-oxide of perfluorotetramethyl Dewar thiophene are uncovered in this work. Dewar rearrangements are chemical processes that occur with a high degree of synchronicity. These changes are directly related to the activation energy.",

keywords = "Dewar thiophenes, Fluxionality, One-electron bonds, Reaction mechanisms",

author = "Sara G{\'o}mez and Edison Osorio and Eugenia Dzib and Rafael Islas and Albeiro Restrepo and Gabriel Merino",

note = "Funding Information: Funding: Partial financial support for this project granted by Universidad de Antioquia via “Estrategia para la sostenibilidad” is acknowledged. This work was funded in Mexico by Conacyt (Grant CB-2015-252356). ED thanks Conacyt for her PhD fellowship. Publisher Copyright: {\textcopyright} 2020 by the authors.",

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doi = "10.3390/molecules25020284",

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AU - Gómez, Sara

AU - Osorio, Edison

AU - Dzib, Eugenia

AU - Islas, Rafael

AU - Restrepo, Albeiro

AU - Merino, Gabriel

N1 - Funding Information: Funding: Partial financial support for this project granted by Universidad de Antioquia via “Estrategia para la sostenibilidad” is acknowledged. This work was funded in Mexico by Conacyt (Grant CB-2015-252356). ED thanks Conacyt for her PhD fellowship. Publisher Copyright: © 2020 by the authors.

PY - 2020/1/1

Y1 - 2020/1/1

N2 - The mechanism for the walk rearrangement in Dewar thiophenes has been clarified theoretically by studying the evolution of chemical bonds along the intrinsic reaction coordinates. Substituent effects on the overall mechanism are assessed by using combinations of the ring (R = H, CF3) and traveling (X = S, S = O, and CH2) groups. The origins of fluxionality in the S-oxide of perfluorotetramethyl Dewar thiophene are uncovered in this work. Dewar rearrangements are chemical processes that occur with a high degree of synchronicity. These changes are directly related to the activation energy.

AB - The mechanism for the walk rearrangement in Dewar thiophenes has been clarified theoretically by studying the evolution of chemical bonds along the intrinsic reaction coordinates. Substituent effects on the overall mechanism are assessed by using combinations of the ring (R = H, CF3) and traveling (X = S, S = O, and CH2) groups. The origins of fluxionality in the S-oxide of perfluorotetramethyl Dewar thiophene are uncovered in this work. Dewar rearrangements are chemical processes that occur with a high degree of synchronicity. These changes are directly related to the activation energy.

KW - Dewar thiophenes

KW - Fluxionality

KW - One-electron bonds

KW - Reaction mechanisms

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JO - Molecules

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Revisiting the rearrangement of Dewar thiophenes

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