Mechanistic characterization of organometallic reactions by nonconventional sampling techniques in mass spectrometry

• Grant number: 20/08894-4
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• Start date: November 01, 2020
• End date: August 31, 2026
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Physical-Chemistry
• Principal Investigator: Thiago Carita Correra
• Grantee: Guilherme Obeid
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• Associated research grant: 14/15962-5 - Reaction mechanism of asymmetric catalysts by mass spectrometry and gas-phase vibrational ion spectroscopy, AP.JP
• Associated scholarship(s): 23/03008-4 - Evaluation of reaction intermediates by gas phase spectroscopy and ion mobility, BE.EP.DD

Abstract

This study aims to evaluate reaction mechanisms mediated by organometallic catalysts, especially the reactions based on Ti and Pd catalysts. These reactions are not only relevant for organic synthesis and widely used in industrial pathways, but also allow experimental techniques to be developed for their evaluation by mass spectrometry, allowing the nature of the chemical species involved in the reactions, especially reaction intermediates, to be characterizedTo evaluate these reactions and to allow the nature of the chemical species to be characterized unequivocally, alternative ways to sample and to promote chemical reactions need to be developed allowing the use of tandem mass spectrometry techniques, like ion vibrational spectroscopy IRMPD that was recently developed in our group.To overcome the challenges imposed by these reactions, like the solvent incompatibility and high reactivity of the reactants, unconventional experimental techniques will be explored, including the use of multiple sprays and desorption electrospray ionization sources (DESI) so the reactions may be promoted in a convenient and controlled way. Therefore, this project consists in a first part where the necessary experimental techniques will be implemented in the mass spectrometer available in our research group, including the tests and validation of these techniques, comparing our results to literature. In a second part, the Sharpless epoxidation and the aminopaladation reaction step, relevant for diverse Pd mediated processes, will be evaluated. (AU)

Scientific publications

(4)

(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)

OBEID, GUILHERME; MORAES, GUSTAVO O.; PENNA, TATIANA C.; SCHENBERG, LEONARDO A.; DUCATI, LUCAS C.; CORRERA, THIAGO C.. Solvation effects on glyphosate protonation and deprotonation states evaluated by mass spectrometry and explicit solvation simulations. Journal of Chemical Physics, v. 158, n. 5, p. 12-pg., 2023-02-07. (20/10246-0, 19/12808-9, 17/20262-0, 17/17750-3, 15/08539-1, 19/18727-0, 19/25634-9, 20/08894-4, 21/06726-0, 14/15962-5)

ESTEVES, LARISSA CERRATO; MACHADO, CAROLINE OLIVEIRA; PIRES GONCALVES, LETICIA CHRISTINA; CAVALCANTE, VICTOR FERNANDES; OBEID, GUILHERME; CORRERA, THIAGO CARITA; BASTOS, ERICK LEITE. Structural Effects on the Antioxidant Properties of Amino Acid Betaxanthins. ANTIOXIDANTS, v. 11, n. 11, p. 19-pg., 2022-11-01. (21/06726-0, 20/08894-4, 19/25634-9, 15/24760-0, 19/15412-9)

RIBEIRO, FRANCISCO WANDERSON MOREIRA; MATSUSHIMA, JULLYANE EMI; OBEID, GUILHERME; VINHATO, ELISANGELA; RODRIGUES, ALESSANDRO; CORRERA, THIAGO CARITA. Mechanistic Investigation of an Organocatalytic Bromocyclization of O-Allyl Carbamates. CHEMCATCHEM, v. 17, n. 8, p. 10-pg., 2025-03-16. (19/25634-9, 21/06726-0, 17/18485-1, 14/15962-5, 15/08539-1, 23/01180-4, 20/08894-4, 22/00498-8, 16/21676-0)

FERNANDES, ANDRE S.; OBEID, GUILHERME; LAURENO, TIAGO J. N.; CORRERA, THIAGO C.. Protonated and Sodiated Cyclophosphamide Fragmentation Pathways Evaluation by Infrared Multiple Photon Dissociation Spectroscopy. Journal of Physical Chemistry A, v. N/A, p. 10-pg., 2023-06-07. (15/08539-1, 19/25634-9, 20/08894-4, 21/06726-0, 14/15962-5)