Abstract

SOTO-SUAREZ, Fátima M.; DUARTE-ALANIZ, Víctor; QUIJANO-QUINONES, Ramiro F.  and  CUEVAS, Gabriel. The Inversion Process of 1,3-cyclohexanedione. J. Mex. Chem. Soc [online]. 2021, vol.65, n.3, pp.424-434.  Epub Feb 14, 2022. ISSN 1870-249X.  https://doi.org/10.29356/jmcs.v65i3.1521.

The inversion process of 1,3-cyclohexanedione was studied to know the energy associated with the chair-chair interconversion. 1,3-cyclohexanedione has a conformational inversion energy of 1.87 kcal/mol evaluated at M06-2x/6-311++G(2d,2p) level of theory. The global process combines inversion and topomerization originated by boat-boat interconversion that includes only two trajectories to the inversion transition state but no six-like cyclohexane, or four-like oxane and thiane. The process includes two different twisted boats associated with a boat transition state. A global scheme is proposed to represent this conformational equilibrium.

Keywords : Inversion; topomerization; 1,3-cyclohanedione; conformational analysis; transition state.

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