In 2018,de Velasco, Diego Antonio Ocampo Gutierrez; Su, Aoze; Zhai, Luhan; Kinoshita, Satowa; Otani, Yuko; Ohwada, Tomohiko published 《Unexpected resistance to base-catalyzed hydrolysis of nitrogen pyramidal amides based on the 7-azabicyclic[2.2.1]heptane scaffold》.Molecules published the findings.COA of Formula: C6H13NO The information in the text is summarized as follows:
Non-planar amides are usually transitional structures, that are involved in amide bond rotation and inversion of the nitrogen atom, but some ground-min. non-planar amides have been reported. Non-planar amides are generally sensitive to water or other nucleophiles, so that the amide bond is readily cleaved. In this article, examine the reactivity profile of the base-catalyzed hydrolysis of 7-azabicyclo[2.2.1]heptane amides I (R = H, Cl, NO2), which show pyramidalization of the amide nitrogen atom, and we compare the kinetics of the base-catalyzed hydrolysis of the benzamides of 7-azabicyclo[2.2.1]heptane and related monocyclic compounds Unexpectedly, non-planar amides based on the 7-azabicyclo[2.2.1]heptane scaffold were found to be resistant to base-catalyzed hydrolysis. The calculated Gibbs free energies were consistent with this exptl. finding. The contribution of thermal corrections (entropy term, -TΔS†) was large; the entropy term (ΔS†) took a large neg. value, indicating significant order in the transition structure, which includes solvating water mols. In addition to this study using trans-4-Aminocyclohexanol, there are many other studies that have used trans-4-Aminocyclohexanol(cas: 27489-62-9COA of Formula: C6H13NO) was used in this study.
trans-4-Aminocyclohexanol(cas: 27489-62-9) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.COA of Formula: C6H13NO
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