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Computational chemistry: a tool to studies of mass spectrometry, reactivity and fragmentation/reaction mechanisms of organic compounds

Abstract

In recent years, the gas-phase chemistry has been the subject of numerous scientific papers and has climbed prominence due to two main events. The development of computational models, improvement of existing ones and advances in data processing, allowing obtaining thermochemical quantities with high accuracy. and the development of current mass spectrometry analysis (MS), which allowed the ionization of molecules, sequential analysis and ion-molecule reaction. The combination between these events has become a useful tool for the growth of many areas of modern chemistry, which further contributes to the understanding of phenomena, per hour, unknown. The computational chemistry in combination with mass spectrometry allows comprises several chemical events which may occur during the ionization and dissociation of a particular compound, through appropriated descriptors, for instance, gas-phase basicity, proton affinities, electron affinities and proton transfers. A provides a quantitative understanding of the structural and energy variations of the ions formed during the possible ionization of the sample, and also the possible pathways of dissociation of ions formed by collision-induced dissociation (CID), thus the indicative of intermediates and transition states. The current project aims developed through the application of current mass spectrometry techniques, such as electrospray ionization (ESI) in combination with computational chemistry for understanding of the reactivity of organic molecules in the gas phase and its mechanisms of fragmentation, thus interpreting their spectra MS/MS by combination with energy, geometric and topological data, which will contribute to the expansion of the results described in the literature and its application by non-specialists and users of different ionization techniques. Nevertheless, the results will be combined with pka values obtained from computational methods in order to suggest the reactivity of compounds in solution. (AU)

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Scientific publications (20)
(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)
BOZZINI, LEANDRO A.; BATISTA, JOAO H. C.; DE MELLO, MURILO B. M.; VESSECCHI, RICARDO; CLOSOSKI, GIULIANO C.. Selective functionalization of cyano-phenyl-2-oxazolines using TMPMgCl center dot LiCl. Tetrahedron Letters, v. 58, n. 44, p. 4186-4190, . (11/12589-3, 14/23604-1, 15/12811-9)
DA SILVA-JUNIOR, E. A.; PALUDO, C. R.; GOUVEA, D. R.; KATO, M. J.; FURTADO, N. A. J. C.; LOPES, N. P.; VESSECCHI, R.; PUPO, M. T.. Gas-phase fragmentation of protonated piplartine and its fungal metabolites using tandem mass spectrometry and computational chemistry. Journal of Mass Spectrometry, v. 52, n. 8, p. 517-525, . (11/01404-2, 09/51812-0, 14/23604-1)
GUARATINI, T.; FEITOSA, L. G. P.; SILVA, D. B.; LOPES, N. P.; LOPES, J. L. C.; VESSECCHI, R.. Gas-phase dissociation study of erythrinian alkaloids by electrospray ionization mass spectrometry and computational methods. Journal of Mass Spectrometry, v. 52, n. 9, p. 571-579, . (14/50265-3, 14/23604-1, 11/13281-2)
MURIE, VALTER E.; NISHIMURA, RODOLFO H. V.; ROLIM, LARISSA A.; VESSECCHI, RICARDO; LOPES, NORBERTO P.; CLOSOSKI, GIULIANO C.. Base-Controlled Regioselective Functionalization of Chloro-Substituted Quinolines. Journal of Organic Chemistry, v. 83, n. 2, p. 871-880, . (15/01466-9, 14/23604-1, 15/12811-9, 15/21364-6)
VESSECCHI, RICARDO; BORGES, LETICIA DA SILVA; EMERY, FLAVIO DA SILVA; LOPES, NORBERTO PEPORINE. Understanding the fragmentation mechanisms of methoxy-, mesyl-, and tosyl-lapachol derivatives by computational chemistry and mass spectrometry analysis. INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, v. 418, n. SI, p. 92-100, . (14/50265-3, 14/23604-1)
SOUZA, AMAURI ALVES; VESSECCHI, RICARDO; CASTRO-GAMBOA, IAN; FURLAN, MAYSA. Combined use of tandem mass spectrometry and computational chemistry to study 2H-chromenes from Piper aduncum. Journal of Mass Spectrometry, v. 54, n. 7, p. 634-642, . (13/07600-3, 17/15014-8, 14/23604-1, 14/50265-3, 14/22239-8)
DIAS, HERBERT J.; VIEIRA, TATIANA M.; CREVELIN, EDUARDO J.; DONATE, PAULO M.; VESSECCHI, RICARDO; CROTTI, ANTONIO E. M.. Fragmentation of 2-aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry. Journal of Mass Spectrometry, v. 52, n. 12, p. 809-816, . (13/20094-0, 14/23604-1)
BOZZINI, LEANDRO A.; DOS SANTOS, THIAGO; MURIE, VALTER E.; DE MELLO, MURILO B. M.; VESSECCHI, RICARDO; CLOSOSKI, GIULIANO C.. Regioselective Functionalization of Ester-, Amide-, Carbonate-, and Carbamate-Substituted 2-Phenyl-2-oxazolines with Mixed Lithium-Magnesium Amides. Journal of Organic Chemistry, v. 86, n. 1, p. 1204-1215, . (18/14150-8, 15/21364-6, 14/23604-1)
NETO, FAUSTO CARNEVALE; ANDREO, MARCIO ADRIANO; RAFTERY, DANIEL; CALLEGARI LOPES, JOAO LUIS; LOPES, NORBERTO PEPORINE; CASTRO-GAMBOA, IAN; DE NORONHA SALES MAIA, BEATRIZ HELENA LAMEIRO; COSTA, EMMANOEL VILACA; VESSECCHI, RICARDO. Characterization of aporphine alkaloids by electrospray ionization tandem mass spectrometry and density functional theory calculations. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, v. 34, n. 3, SI, . (09/08281-3, 03/02176-7, 14/12343-2, 14/23604-1, 14/50265-3, 10/07564-9)
DIAS, HERBERT J.; BAGUENARD, MANON; CREVELIN, EDUARDO J.; PALARETTI, VINICIUS; GATES, PAUL J.; VESSECCHI, RICARDO; CROTTI, ANTONIO E. M.. Gas-phase fragmentation reactions of protonated benzofuran- and dihydrobenzofuran-type neolignans investigated by accurate-mass electrospray ionization tandem mass spectrometry. Journal of Mass Spectrometry, v. 54, n. 1, p. 35-46, . (14/23604-1, 13/20094-0)
AGUIAR, GABRIELA P.; CREVELIN, EDUARDO J.; DIAS, HERBERT J.; AMBROSIO, SERGIO R.; BASTOS, JAIRO K.; HELENO, VLADIMIR C. G.; VESSECCHI, RICARDO; CROTTI, ANTONIO E. M.. Electrospray ionization tandem mass spectrometry of labdane-type acid diterpenes. Journal of Mass Spectrometry, v. 53, n. 11, p. 1086-1096, . (13/20094-0, 11/13630-7, 14/23604-1, 12/22832-5)
SILVA, SIMONE CAVALCANTE; RODRIGUES, SHIRLEY M. M.; NARDINI, VIVIANI; VAZ, ARTUR DE L. L.; PALARETTI, VINICIUS; JOSE DA SILVA, GIL VALDO; VESSECCHI, RICARDO; CLOSOSKI, GIULIANO C.. Conformational dynamics of 4-formylaminoantipyrine based on NMR and theoretical calculations. Journal of Molecular Structure, v. 1163, p. 280-286, . (14/23604-1, 15/12811-9)
MOREIRA, FERNANDA DE LIMA; HABENSCHUS, MAISA D.; BARTH, THIAGO; MARQUES, LUCAS M. M.; PILON, ALAN CESAR; BOLZANI, VANDERLAN DA SILVA; VESSECCHI, RICARDO; LOPES, NORBERTO P.; DE OLIVEIRA, ANDERSON R. M.. Metabolic profile and safety of piperlongumine. SCIENTIFIC REPORTS, v. 6, . (14/23604-1, 13/17658-9, 14/50265-3)
PINTO, ANGELO DA CUNHA; VESSECCHI, RICARDO; DA SILVA, CARMELITA GOMES; LOURENCO AMORIM, ANA CAROLINA; DOS SANTOS JUNIOR, HELVECIO MARTINS; CUNHA REZENDE, MICHELLE JAKELINE; GATES, PAUL J.; REZENDE, CLAUDIA MORAES; LOPES, NORBERTO PEPORINE. Electrospray ionization tandem mass spectrometry analysis of isopimarane diterpenes from Velloziaceae. Rapid Communications in Mass Spectrometry, v. 30, n. 1, p. 61-68, . (14/23604-1)
DOS SANTOS, FERNANDA M.; BATISTA, JOAO H. C.; VESSECCHI, RICARDO; CLOSOSKI, GIULIANO C.. Directed Functionalization of Cyano-Substituted Furans and Thiophenes with TMPMgCl center dot LiCl. Synlett, v. 26, n. 20, p. 2795-2800, . (13/04766-8, 14/23604-1, 12/13740-0)
MARQUES, LUCAS M. M.; CALLEJON, DANIEL R.; PINTO, LARISSA G.; DE CAMPOS, MICHEL L.; DE OLIVEIRA, ANDERSON R. M.; VESSECCHI, RICARDO; ADHIKARI, ACHYUT; SHRESTHA, RAM L. S.; PECCININI, ROSANGELA G.; LOPES, NORBERTO P.. Pharmacokinetic properties, in vitro metabolism and plasma protein binding of govaniadine an alkaloid isolated from Corydalis govaniana Wall. Journal of Pharmaceutical and Biomedical Analysis, v. 131, p. 464-472, . (13/16496-5, 13/17658-9, 14/23604-1, 14/13192-8)
DEMARQUE, DANIEL P.; CROTTI, ANTONIO E. M.; VESSECCHI, RICARDO; LOPES, JOAO L. C.; LOPES, NORBERTO P.. Fragmentation reactions using electrospray ionization mass spectrometry: an important tool for the structural elucidation and characterization of synthetic and natural products. NATURAL PRODUCT REPORTS, v. 33, n. 3, p. 432-455, . (14/20302-4, 13/20094-0, 14/23604-1, 14/50265-3, 14/18052-0)
DIAS, HERBERT JUNIOR; STEFANI, RICARDO; TOMAZ, JOSE CARLOS; VESSECCHI, RICARDO; MILLER CROTTI, ANTONIO EDUARDO. Differentiation between 3,4-and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry. JOURNAL OF ANALYTICAL METHODS IN CHEMISTRY, . (13/20094-0, 14/23604-1)
GAZOLLA, MATHEUS COUTINHO; MAURIZ MARQUES, LUCAS MACIEL; GAMA E SILVA, MARIANA; MOURA FONTES ARAUJO, MARIA TAIS; MENDES, ROSEMAIRY LUCIANE; GUEDES DA SILVA ALMEIDA, JACKSON ROBERTO; VESSECCHI, RICARDO; LOPES, NORBERTO PEPORINE. Characterization of 3-aminospirostane alkaloids from roots of Solanum paniculatum L. with hepatoprotective activity. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, . (14/50265-3, 17/19330-1, 14/23604-1)

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