Please use this identifier to cite or link to this item: https://repositorio.uca.edu.ar/handle/123456789/9025
Título : On the effect of intramolecular H-bonding in the configurational assessment of polyhydroxylated compounds with computational methods : The hyacinthacines case
Autor : Zanardi, María Marta 
Sortino, Maximiliano A. 
Sarotti, Ariel M. 
Palabras clave : ISOMEROSMETODO COMPUTACIONALQUIMICA
Fecha de publicación : 2019
Editorial : Elsevier
Cita : Zanardi, M. M., Sortino, M. A., Sarotti, A. M. On the effect of intramolecular H-bonding in the configurational assessment of polyhydroxylated compounds with computational methods : The hyacinthacines case [en línea]. Carbohydrate Research. 2019, 474. doy: https://doi.org/10.1016/j.carres.2019.01.011. Disponible en: https://repositorio.uca.edu.ar/handle/123456789/9025
Resumen : Abstract: Hyacinthacines are important members of the pyrrolizidine family, with several compounds having ambiguous, revised or unverified structures. Herein we thoroughly explored the performance DP4 and DP4+ for the in silico stereoassignment of hyacinthacines A1, A2 and five synthetic isomers. The results suggested that the quality of the predictions strongly depended on the conformational landscape provided by DFT energies, with five compounds correctly assigned. In the two cases incorrectly classified we found that the source of the problem was conformational in nature, with spurious conformations being considerably over-stabilized by intramolecular H-bondings. We showed that neglecting such shapes resulted in a noteworthy improvement, with all compounds correctly assigned in high confidence (>99.9%).
URI : https://repositorio.uca.edu.ar/handle/123456789/9025
ISSN : 0008-6215
Disciplina: QUIMICA
DOI: https://doi.org/10.1016/j.carres.2019.01.011
Derechos: Acceso abierto. 2 años de embargo
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