Synthesis of fluorinated derivatives of thymol and carvacrol and study of their physico-chemical properties

• Grant number: 19/03855-3
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: April 01, 2019
• End date: January 31, 2021
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Rodrigo Antonio Cormanich
• Grantee: Bruno de Almeida Piscelli
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated research grant: 18/03910-1 - Physicochemical studies of fluorinated organic compounds: experimental and theoretical approaches, AP.JP

Abstract

It is intended to make the fluorination by means of simple methodologies in organic synthesis, obtaining diazonium salts at different positions of the benzene ring for later fluorination of them. The physic-chemical properties of thymol and carvacrol are expected to be considerably different after inclusion of the fluorine atoms, which may present properties of interest to areas such as medicinal chemistry and agrochemicals. For physic-chemical studies of the compounds, it is intended to use 1H and 19F NMR. In addition, theoretical calculations of electronic structure, using Functional Density Theory ("DFT") and/or ab initio, with several basis sets available in commercial software packages such as GAUSSIAN-09, may be used for comparison and elucidation of experimental results.

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

PISCELLI, BRUNO A.; SANDERS, WILLIAM; YU, CIHANG; AL MAHARIK, NAWAF; LEBL, THOMAS; CORMANICH, RODRIGO A.; O'HAGAN, DAVID. Fluorine-Induced Pseudo-Anomeric Effects in Methoxycyclohexanes through Electrostatic 1,3-Diaxial Interactions. CHEMISTRY-A EUROPEAN JOURNAL, v. 26, n. 52, AUG 2020. (18/03910-1, 19/05028-7, 19/03855-3)

CLARK, JOSHUA L.; TAYLOR, ALARIC; GEDDIS, AILSA; NEYYAPPADATH, RIFAHATH M.; PISCELLI, BRUNO A.; YU, CIHANG; CORDES, DAVID B.; SLAWIN, ALEXANDRA M. Z.; CORMANICH, RODRIGO A.; GULDIN, STEFAN; et al. Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs. CHEMICAL SCIENCE, v. 12, n. 28, p. 9712-9719, JUL 28 2021. (18/03910-1, 19/03855-3)

PISCELLI, BRUNO A.; O'HAGAN, DAVID; CORMANICH, RODRIGO A.. The contribution of non-classical CHaxMIDLINE HORIZONTAL ELLIPSISOC hydrogen bonds to the anomeric effect in fluoro and oxa-methoxycyclohexanes. Physical Chemistry Chemical Physics, v. 23, n. 10, p. 5845-5851, MAR 14 2021. (18/03910-1, 19/03855-3, 19/05028-7)