Author/Authors :
Martínez-Cabrera, Miguel A. Universidad Nacional de Asunción - Facultad de Ciencias Exactas y Naturales - Departamento de Biología - Área Química Orgánica de los Productos Naturales-LAREV, San Lorenzo Campus - UNA, Paraguay , Macías, Mario A. Department of Chemistry - Universidad de los Andes, Colombia , Ferreira, Francisco Cryssmat-Lab/DETEMA - Facultad de Química - Universidad de la República, Uruguay , Pandolfi, Enrique Laboratorio de Síntesis Orgánica, DQO - Facultad de Química - Universidad de la República, Uruguay , Barúa, Javier Universidad Nacional de Asunción - Facultad de Ciencias Químicas - San Lorenzo Campus-UNA, Paraguay , Suescun, Leopoldo Cryssmat-Lab/DETEMA - Facultad de Química - Universidad de la República, Uruguay
Abstract :
Lapachol acetate [systematic name: 3-(3-methylbut-2-enyl)-1,4-dioxonaphthalen-2-yl acetate], C17H16O4, was prepared using a modified high-yield procedure and its crystal structure is reported for the first time 80 years after its first synthesis. The full spectroscopic characterization of the molecule is reported. The molecular conformation shows little difference with other lapachol derivatives and lapachol itself. The packing is directed by intermolecular π–π and C—H⋯O interactions, as described by Hirshfeld surface analysis. The former interactions make the largest contributions to the total packing energy in a ratio of 2:1 with respect to the latter.
Keywords :
crystal structure , naphthoquinone , lapachol acetate , synthesis , Hirshfeld analysis
