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Reaction mechanism of asymmetric catalysts by mass spectrometry and gas-phase vibrational ion spectroscopy

Grant number: 14/15962-5
Support Opportunities:Research Grants - Young Investigators Grants
Duration: May 01, 2015 - June 30, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Physical-Chemistry
Principal Investigator:Thiago Carita Correra
Grantee:Thiago Carita Correra
Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
Associated researchers:Jose Manuel Riveros Nigra
Associated grant(s):21/06726-0 - Investigation of reactive intermediates in complex chemical and biochemical processes, AP.JP2
15/08539-1 - Multi-User Equipment approved in grant 2014/15962-5: ion trap mass spectrometer modified to perform infrared vibrational spectroscopy (IRMPD), AP.EMU
Associated scholarship(s):20/08894-4 - Mechanistic characterization of organometallic reactions by nonconventional sampling techniques in mass spectrometry, BP.DD
19/22047-5 - Mechanistic evaluation of carbodiimides by mass spectrometry, BP.MS
19/12808-9 - Glyphosate protonation and metal coordination sites, BP.IC
+ associated scholarships 17/20262-0 - Unraveling electrochemical reaction intermediates by mass spectrometry coupled to ion vibrational spectroscopy, BP.PD
17/22441-0 - Ion trap mass spectrometer modified to perform infrared vibrational spectroscopy, BP.TT
17/18485-1 - Mechanistic studies of haloamination reactions promoted by metallic and organic catalysts, BP.DR
16/19698-6 - Instrumental development for mechanistic studies, BP.MS
15/11769-9 - Isolation of Sharpless reaction intermediates epoxidation and characterization of these species by theoretical calculations, BP.IC - associated scholarships


This project intends to evaluate the reaction mechanisms of catalysts both in condensed and in the gas phase experimentally, by the use of mass spectrometry techniques like reaction intermediate fishing and vibrational ion spectroscopy (IRMPD), which is unprecedented in Brazil.IRMPD spectroscopy consists on the evaluation of ion dissociation in the gas phase promoted by a tunable infrared radiation, which is proportional to the absorption of energy at a given wavelength. The infrared spectrum obtained by this technique can be used to evaluate the conformational equilibrium and connectivity of ions, tasks that cannot be carried out by ordinary mass to charge ratio (m/z) measurements.The target systems of this proposal will be: i) the metal center catalysts, of which the Sharpless chiral reaction mediated by titanium alkoxides and chiral tartrates will be the first system to be evaluated, ii) the coordination of metal and model ligands, allowing the evaluation of the pre-catalyst assembly and activation in solution and, iii) the evaluation of organocatalysts and their reaction intermediates, like the iminium based MacMillan's imidazolidinones.Instrumentation design also plays an important role in this project, once the infrared ion spectroscopy in the gas phase is not available in commercial instruments and is, in fact, a novel technique in BrazilThis project will be supported by varied theoretical calculation methodologies, allowing the evaluation of conformer stabilities and reaction energy landscapes, giving a detailed picture of the systems in the molecular level.This proposal aims to elucidate the reaction mechanism of diverse catalysts by the synergic use of a novel technique and theoretical calculations, not only allowing the description of important reactions mechanism for widespread catalysts, but also helping in the development of new reactions and catalysts. (AU)

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Scientific publications (18)
(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)
PENNA, TATIANA C.; CERVI, GUSTAVO; RODRIGUES-OLIVEIRA, ANDRE F.; YAMADA, BRUNO D.; LIMA, RAFAEL Z. C.; MENEGON, JAIR J.; BASTOS, ERICK L.; CORRERA, THIAGO C.. Development of a photoinduced fragmentation ion trap for infrared multiple photon dissociation spectroscopy. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, . (14/15962-5, 15/08539-1, 16/19698-6, 19/06391-8, 17/20262-0, 18/20592-3)
PRINCIVAL, CLEVERSON R.; ARCHILHA, MARCOS V. L. R.; DOS SANTOS, ALCINDO A.; FRANCO, MAURICIO P.; BRAGA, ATAUALPA A. C.; RODRIGUES-OLIVEIRA, ANDRE F.; CORRERA, THIAGO C.; CUNHA, RODRIGO L. O. R.; COMASSETO, JOAO V.. Stability Study of Hypervalent Tellurium Compounds in Aqueous Solutions. ACS OMEGA, v. 2, n. 8, p. 4431-4439, . (14/15962-5, 15/08539-1)
CORRERA, THIAGO C.; FERNANDES, ANDRE S.; RIVEROS, JOSE M.. Dynamic/Thermochemical Balance Drives Unusual Alkyl/F Exchange Reactions in Siloxides and Analogs. Journal of Physical Chemistry A, v. 120, n. 10, p. 1644-1651, . (14/15962-5)
TRIPODI, GUILHERME L.; CORRERA, THIAGO C.; ANGOLINI, CELIO F. F.; FERREIRA, BRUNO R. V.; MAITRE, PHILIPPE; EBERLIN, MARCOS N.; ROITHOVA, JANA. The Intermediates in Lewis Acid Catalysis with Lanthanide Triflates. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2019, n. 22, p. 3560-3566, . (14/15962-5, 15/08539-1)
RODRIGUES-OLIVEIRA, ANDRE F.; RIBEIRO, FRANCISCO W. M.; CERVI, GUSTAVO; CORRERA, THIAGO C.. Evaluation of Common Theoretical Methods for Predicting Infrared Multiphotonic Dissociation Vibrational Spectra of Intramolecular Hydrogen-Bonded Ions. ACS OMEGA, v. 3, n. 8, p. 9075-9085, . (14/15962-5, 17/18485-1, 16/19698-6, 15/08539-1)
FERNANDES, ANDRE SANTOS; MAITRE, PHILIPPE; CORRERA, THIAGO CARITA. Evaluation of the Katsuki-Sharpless Epoxidation Precatalysts by ESI-FTMS, CID, and IRMPD Spectroscopy. Journal of Physical Chemistry A, v. 123, n. 5, p. 1022-1029, . (15/11769-9, 14/15962-5, 15/08539-1)
RODRIGUES-OLIVEIRA, ANDRE F.; BATISTA, PATRICK R.; DUCATI, LUCAS C.; CORRERA, THIAGO C.. Analyzing the N-H+center dot center dot center dot pi interactions of protonated tryptophan and phenylalkylamines using QTAIM, NCl, and NBO. THEORETICAL CHEMISTRY ACCOUNTS, v. 139, n. 8, . (19/25634-9, 14/15962-5, 15/08539-1, 18/07308-4)
MASSON, MARIA ANGELICA C.; KARPFENSTEIN, RENAN; DE OLIVEIRA-SILVA, DIOGO; TEULER, JEAN-MARIE; ARCHIREL, PIERRE; MAITRE, PHILIPPE; CORRERA, THIAGO C.. Evaluation of Ca2+ Binding Sites in Tacrolimus by Infrared Multiple Photon Dissociation Spectroscopy. Journal of Physical Chemistry B, v. 122, n. 43, p. 9860-9868, . (15/08539-1, 14/15962-5)
BARBEIRO, CRISTIANE S.; VASCONCELOS, STANLEY N. S.; ZUKERMAN-SCHPECTOR, JULIO; CARACELLI, IGNEZ; PIMENTA, DANIEL C.; RODRIGUES, ANA CLARA B.; FERNANDES, ANDRE S.; CORRERA, THIAGO C.; BASTOS, ERICK L.; STEFANI, HELIO A.. Chlorinated 2-hydroxynaphthalenoxazolines: Synthesis, Reaction Mechanism and Fluorescence Properties. CHEMISTRYSELECT, v. 1, n. 18, p. 5647-5652, . (13/17960-7, 14/15962-5, 15/11769-9)
PAPA SPADAFORA, BRUNA; MOREIRA RIBEIRO, FRANCISCO WANDERSON; MATSUSHIMA, JULLYANE EMI; ARIGA, ELAINE MIHO; OMARI, ISAAC; SOARES, PRISCILA MACHADO ARRUDA; DE OLIVEIRA-SILVA, DIOGO; VINHATO, ELISANGELA; MCINDOE, J. SCOTT; CARITA CORRERA, THIAGO; et al. Regio- and diastereoselective Pd-catalyzed aminochlorocyclization of allylic carbamates: scope, derivatization, and mechanism. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 19, n. 25, . (19/16026-5, 16/21676-0, 15/08539-1, 16/17328-7, 17/18485-1, 14/15962-5, 19/25634-9)
BATISTA, PATRICK R.; PENNA, TATIANA C.; DUCATI, LUCAS C.; CORRERA, THIAGO C.. p-Aminobenzoic acid protonation dynamics in an evaporating droplet by ab initio molecular dynamics. Physical Chemistry Chemical Physics, v. 23, n. 35, . (17/20262-0, 20/10246-0, 19/25634-9, 18/07308-4, 15/08539-1, 14/15962-5)
ESTEVES, LARISSA C.; PINHEIRO, AMANDA C.; PIOLI, RENAN M.; PENNA, TATIANA C.; BAADER, WILHELM J.; CORRERA, THIAGO C.; BASTOS, ERICK L.. Revisiting the Mechanism of Hydrolysis of Betanin. Photochemistry and Photobiology, v. 94, n. 5, p. 853-864, . (15/18474-4, 14/22136-4, 15/08539-1, 14/15962-5, 16/21445-9)
RIBEIRO, FRANCISCO W. M.; RODRIGUES-OLIVEIRA, ANDRE F.; CORRERA, THIAGO C.. Benzoxazine Formation Mechanism Evaluation by Direct Observation of Reaction Intermediates. Journal of Physical Chemistry A, v. 123, n. 38, p. 8179-8187, . (14/15962-5, 15/08539-1, 17/18485-1)
SOUZA, DIEGO H. P.; GUIMARAES, ROBSON R.; CORRERA, THIAGO C.; ZAMARION, VITOR M.. Investigation of the photocatalytic activity of titanium dioxide films under visible light measured by electrospray mass spectrometry. NEW JOURNAL OF CHEMISTRY, v. 42, n. 22, p. 18259-18268, . (17/09469-2, 14/15962-5, 15/08539-1, 16/18354-1)
CORRERA, THIAGO CARITA; FERNANDES, ANDRE SANTOS; REGINATO, MARCELO MOTA; DUCATI, LUCAS COLUCCI; BERDEN, GIEL; OOMENS, JOS. Probing the geometry reorganization from solution to gas-phase in putrescine derivatives by IRMPD, H-1-NMR and theoretical calculations. Physical Chemistry Chemical Physics, v. 19, n. 35, p. 24330-24340, . (15/08541-6, 15/11769-9, 15/08539-1, 14/21930-9, 14/15962-5)
DE OLIVEIRA, ISADORA M.; VASCONCELOS, STANLEY S. N.; BARBEIRO, CRISTIANE S.; CORRERA, THIAGO C.; SHAMIM, ANWAR; PIMENTA, DANIEL C.; CARACELLI, IGNEZ; ZUKERMAN-SCHPECTOR, JULIO; STEFANI, HELIO A.; MANARIN, FLAVIA. Ytterbium(III)-catalyzed three-component reactions: synthesis of 4-organoselenium-quinolines. NEW JOURNAL OF CHEMISTRY, v. 41, n. 18, p. 9884-9888, . (13/17960-7, 12/00424-2, 14/15962-5, 16/04289-3)
TATIANA C. PENNA; THIAGO C. CORRERA. TÉCNICAS AVANÇADAS PARA A DIFERENCIAÇÃO DE ISÔMEROS POR ESPECTROMETRIA DE MASSAS. Química Nova, v. 43, n. 8, p. 1125-1137, . (15/08539-1, 14/15962-5, 17/20262-0)

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