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Studies on the Configurational Stability of Tropolone-Ketone-, Ester-, and Aldehyde-Based Chiral Axes.
Baucom, John-Charles; Agyemang, Nana B; Trelles, Theresa; Gallicchio, Emilio; Murelli, Ryan P.
Afiliación
  • Baucom JC; Department of Chemistry and Biochemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, United States.
  • Agyemang NB; PhD Program in Chemistry, The Graduate Center of the City University of New York, New York, New York 10016, United States.
  • Trelles T; Department of Chemistry and Biochemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, United States.
  • Gallicchio E; PhD Program in Chemistry, The Graduate Center of the City University of New York, New York, New York 10016, United States.
  • Murelli RP; Department of Chemistry and Biochemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, United States.
J Org Chem ; 89(1): 541-552, 2024 Jan 05.
Article en En | MEDLINE | ID: mdl-38133833
ABSTRACT
Recent studies have revealed that tropolone-amide aryl C-C(O) rotational barriers are dramatically higher than those of analogous benzamide-based systems, and as a result, they have an increased likelihood of displaying high configurational stability. Studies on other tropolone-based chiral axes are important to assess the generality of this phenomenon. Herein, we describe a series of studies on the rotational barriers of tropolone-ketone, tropolone-ester, and tropolone-aldehyde chiral axes. These studies are complemented with computational modeling of the dynamics of these and analogous benzenoid variants to illuminate the impact that tropolone may have on aryl-C(O) configurational stability.

Texto completo: 1 Bases de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2024 Tipo del documento: Article País de afiliación: Estados Unidos

Texto completo: 1 Bases de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2024 Tipo del documento: Article País de afiliación: Estados Unidos