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Introduction
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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

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El oxirano tiatiónico.

Peter R Schreiner1, Hans Peter Reisenauer, Jaroslaw Romanski

  • 1Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany. prs@org.chemie.uni-giessen.de

Journal of the American Chemical Society
|May 11, 2010
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores sintetizaron la esquiva molécula de oxatiiranos madre de la sulfina utilizando la fotoquímica. Este avance proporciona información sobre las reacciones de transferencia de azufre y la estabilidad de los compuestos que contienen azufre.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • La fotoquímica es la fotoquímica.
  • Química computacional es la química computacional.

Sus antecedentes:

  • Los heterociclos que contienen azufre son cruciales en varias reacciones químicas.
  • El oxatiirano progenitor ha sido una molécula largamente buscada pero no caracterizada.
  • Comprender la estabilidad y la reactividad de estos compuestos es clave para avanzar en la química del azufre.

Objetivo del estudio:

  • Para lograr la primera síntesis de la madre oxatiiran.
  • Para caracterizar la estructura y la estabilidad del oxatiiran.
  • Para comparar la estabilidad del oxatiiran con su análogo de oxígeno, el dioxiran.

Principales métodos:

  • Reorganización fotoquímica de la sulfina mediante el uso de la luz (lambda = 313 +/- 10 nm).
  • Aislamiento y caracterización en una matriz de argón (Ar) a temperaturas criogénicas (11 K).
  • Química computacional de alto nivel (CCSD(T) /cc-pVTZ) para el análisis de frecuencias vibratorias.

Principales resultados:

  • Preparación y caracterización exitosas del oxatiiran de origen.
  • La excelente concordancia entre las frecuencias vibratorias experimentales y las computadas confirmó la estructura.
  • El oxatiiran es menos estable que la sulfina en aproximadamente 10 kcal mol ((-1).

Conclusiones:

  • La síntesis de oxatiirane proporciona un nuevo bloque de construcción para la química del azufre.
  • La relativa inestabilidad en comparación con la sulfina se atribuye a los efectos electrónicos.
  • Los oxatiiranos son probablemente importantes intermediarios en las reacciones de transferencia de azufre.