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

• Grant number: 17/04819-5
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: September 01, 2017
• End date: December 31, 2018
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Physical-Chemistry
• Principal Investigator: Ricardo Vessecchi Lourenço
• Grantee: Letícia da Silva Borges
• Host 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)

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)

BORGES, LETICIA DA SILVA; CARVALHO BATISTA, JOAO HENRIQUE; BOZZINI, LEANDRO; LOURENCO JR, CELSO DONIZETE; LOPES, NORBERTO PEPORINE; CLOSOSKI, GIULIANO CESAR; VESSECCHI, RICARDO. Are benzoylium and nitrilium ions produced from substituted 2-arene-2-oxazolines during mass spectrometry? A study based on density functional theory calculations, quantum theory of atoms in molecules, and electrospray ionization tandem mass spectrometry. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, v. 37, n. 4, p. 11-pg., 2023-02-28. (17/04819-5, 09/51812-0, 09/08281-3, 14/50265-3, 20/02207-5, 18/14150-8, 14/23604-1)