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Computational chemistry in studies of the reactivity of oxazolines: combining theory and experiment

Grant number: 17/04819-5
Support type:Scholarships in Brazil - Scientific Initiation
Effective date (Start): September 01, 2017
Effective date (End): December 31, 2018
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Ricardo Vessecchi Lourenço
Grantee:Letícia da Silva Borges
Home Institution: Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto (FFCLRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
Associated research grant:14/50265-3 - Distribution and metabolism of natural and synthetic xenobiotics: from the comprehension of reactional process to tissue imaging generation, AP.BTA.TEM

Abstract

Oxazolines have attracted attention due to their versatility as carboxylic acid protecting groups, chiral auxiliaries, and ligands for asymmetric catalysis. 2-oxazoline derivatives have been widely studied because is interesting from a chemical viewpoint, due to their reactivity and potential biological activities. Mass spectrometry analysis can contribute to understand the reactivity and to develop new methods to characterize these compounds. In this context, computational chemistry has been successfully employed in mass spectrometry fragmentation analysis. Thus, in this work, some 2-oxazoline derivatives will be studied through computational thermochemical parameters using DFT calculations, and the reactivity of these compounds will be compared to mass spectra obtained from ESI-MS/MS experiments. The main purpose of this work is studying the variations at geometry, topology, and thermochemical after protonation and deprotonation using QTAIM and computational thermochemistry. An interesting discussion on the reactivity in terms of proton interaction and gas-phase chemistry must be done in order to establish the protonation sites from MEP, atomic charges and frontiers orbitals (AU)