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Physicochemical studies of fluorinated organic compounds: experimental and theoretical approaches

Grant number: 18/03910-1
Support type:Research Grants - Young Investigators Grants
Duration: November 01, 2018 - October 31, 2022
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Rodrigo Antonio Cormanich
Grantee:Rodrigo Antonio Cormanich
Home Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
Associated grant(s):19/24758-6 - Multi-User Equipment approved in grant 2018/03910-1: X-Pulse HF benchtop NMR system, AP.EMU
19/20522-8 - Multi-User Equipment approved in grant 2018/03910-1: EasyMax 102 advanced automated reactor, AP.EMU
19/05028-7 - Physico-chemical studies of organofluorine compounds: experimental and theoretical approaches, AV.EXT
Associated scholarship(s):21/09716-5 - Synthesis, physicochemical properties and crystal structure simulations of organofluorine compounds, BP.DD
20/13525-8 - Study of helical vs zigzag geometry of perfluorinated compounds capable of forming intramolecular hydrogen bonds, BP.IC
20/06536-3 - Fluorinase reactive substrate analysis, BP.MS
+ associated scholarships 19/21136-4 - Mechanistic studies for the evaluation of the Thorpe-Ingold effect of CF2 groups in intramolecular cyclization reactions, BP.MS
19/03855-3 - Synthesis of fluorinated derivatives of thymol and carvacrol and study of their physico-chemical properties, BP.IC
18/21979-9 - Physical organic chemistry studies of peroxides and dissulfides for the understanding of their properties and reactivities, BP.IC - associated scholarships


It is proposed the physicochemical study of organofluorinated compounds, which include their synthesis and characterization and the monitoring of its reaction mechanisms with the integrated use of 1H, 13C and 19F NMR and infrared spectroscopy and theoretical calculations of electronic structure. With the aid of the jovem pesquisador project it will be possible to implement modern methods of investigation of organic reaction mechanisms, which are insipient in Brazil, by monitoring reactions in situ in the reaction flask itself. In addition, the approval of this project is essential for a consolidation of the new research group of studies of fluorinated organic compounds that are intended to start at the IQ-UNICAMP, whose area is not studied in our country. For the present jovem pesquisador project, in which four master's scholarships are being requested, molecular systems were chosen for some case studies, which discuss very important aspects in constant discussion in the literature on physicochemical properties and reactivities of organofluorinated compounds and their applications. In the first case, it is intended to study the structure of fluorinated polymers in order to elucidate the effects that lead to their macroscopic physical-chemical properties. In the second case, we intend to investigate the mechanisms of reaction and the Thorpe-Ingold effect caused by the CF2 group in intramolecular cyclization reactions. A third project aim is to evaluate how the fluorine atom behaves as a proton receptor in intra- and intermolecular hydrogen bonds in fluorothiols. In the fourth project we intend to study the effect of CF2 groups on macrocycles such as crown ethers, which may have their interactions with ions increased relative to the non-fluorinated ones. The results obtained by the various experimental and theoretical methods applied here will be compared. In this way, it is expected that the integration of experimental and theoretical chemistries may help to highlight the obtained results and that both may help in the detailed descriptions of the results. In fact, it is expected to obtain complementary results between the various experimental and theoretical methods that will be applied and obtain results that none of them alone could achieve. Thus, the aim is to consolidate a new research group on the chemistry of fluorinated organic compounds and the investigation of reaction mechanisms at IQ-UNICAMP. The approval of this project will be extremely important in order to make it possible to implement the new experimental and theoretical methods that will be applied. Thus the present project of Jovem Pesquisador aims at the implementation of new lines of research and modern methods in mechanistic and structural studies of organic compounds. (AU)

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Scientific publications (16)
(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)
ANDRADE, LAIZE A. F.; ZEOLY, LUCAS A.; CORMANICH, RODRIGO A.; FREITAS, MATHEUS P.. Conformational signature of Ishikawa's reagent using NMR information from diastereotopic fluorines. Beilstein Journal of Organic Chemistry, v. 15, p. 506-512, . (18/03910-1)
SIMOES, LUIS H.; CORMANICH, RODRIGO A.. Stereoelectronic Effects in Multivicinal Fluoroalkanes and Conformational Implications. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2020, n. 4, . (18/03910-1)
DE GIOVANETTI, MARINELLA; FERRAZ BITENCOURT, LUIS FELIPE; CORMANICH, RODRIGO; SAUER, STEPHAN P. A.. n the Unexpected Accuracy of the M06L Functional in the Calculation of (1)J(FC) Spin-Spin Coupling Constant. JOURNAL OF CHEMICAL THEORY AND COMPUTATION, v. 17, n. 12, p. 7712-7723, . (18/03910-1, 19/24788-2)
STIVANIN, MATEUS L.; GALLO, RAFAEL D. C.; SPADETO, JOAO PAULO M.; CORMANICH, RODRIGO A.; JURBERG, IGOR D.. visible light-mediated three-component strategy based on the ring-opening of cyclic ethers with aryldiazoacetates and nucleophile. ORGANIC CHEMISTRY FRONTIERS, v. 9, n. 5, p. 1321-1326, . (20/00144-6, 20/06536-3, 18/03910-1, 19/01235-8)
MENEZES SPADETO, JOAO PAULO; FREITAS, MATHEUS P.; CORMANICH, RODRIGO A.. Fluorinated dihydropyridines as candidates to block L-type voltage-dependent calcium channels. JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, . (20/06536-3, 18/03910-1)
ZHANG, HUAIYUAN; CORMANICH, RODRIGO A.; WIRTH, THOMAS. Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based lambda(3)-Iodanes. CHEMISTRY-A EUROPEAN JOURNAL, . (18/03910-1)
AFONSO, MARCO A. S.; CORMANICH, RODRIGO A.. The preferred geometry of hydroperoxides is the result of an interplay between electrostatic and hyperconjugative effects. Physical Chemistry Chemical Physics, v. 22, n. 46, p. 27173-27177, . (18/21979-9, 18/03910-1)
PISCELLI, BRUNO A.; SANDERS, WILLIAM; YU, CIHANG; AL MAHARIK, NAWAF; LEBL, THOMAS; CORMANICH, RODRIGO A.; O'HAGAN, DAVID. Fluorine-Induced Pseudo-Anomeric Effects in Methoxycyclohexanes through Electrostatic 1,3-Diaxial Interactions. CHEMISTRY-A EUROPEAN JOURNAL, v. 26, n. 52, . (18/03910-1, 19/05028-7, 19/03855-3)
FERNANDES, ALESSANDRA A. G.; DA SILVA, AMANDA F.; OKADA, JR., CELSO Y.; SUZUKAWA, VITOR; CORMANICH, RODRIGO A.; JURBERG, IGOR D.. General Platform for the Conversion of Isoxazol-5-ones to 3,5-Disubstituted Isoxazoles via Nucleophilic Substitutions and Palladium Catalyzed Cross-Coupling Strategies. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2019, n. 19, p. 3022-3034, . (17/22164-6, 17/24017-0, 18/03910-1)
DA SILVA, AMANDA F.; AFONSO, MARCO A. S.; CORMANICH, RODRIGO A.; JURBERG, IGOR D.. Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation. CHEMISTRY-A EUROPEAN JOURNAL, v. 26, n. 25, . (18/03910-1, 18/21979-9, 17/24017-0)
ZEOLY, LUCAS A.; COELHO, FERNANDO; CORMANICH, RODRIGO A.. Intramolecular H-Bond Is Formed in 2-Fluorophenol and 2-Fluorothiophenol, but It May Not Be the Main Pathway of the J(FH) Coupling Constant Transmission. Journal of Physical Chemistry A, v. 123, n. 46, p. 10072-10078, . (18/03910-1)
PISCELLI, BRUNO A.; O'HAGAN, DAVID; CORMANICH, RODRIGO A.. The contribution of non-classical CHaxMIDLINE HORIZONTAL ELLIPSISOC hydrogen bonds to the anomeric effect in fluoro and oxa-methoxycyclohexanes. Physical Chemistry Chemical Physics, v. 23, n. 10, p. 5845-5851, . (18/03910-1, 19/03855-3, 19/05028-7)
SPADETO, JOAO P. M.; CORMANICH, RODRIGO A.; FRANCA, TANOS C. C.; LAPLANTE, STEVEN R.; GONCALVES, ARLAN S.. Docking and molecular dynamics studies of potential new leads against DBL3x derived from chondroitin sulfate A (CSA): a new approach for the treatment of malaria. JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, . (18/03910-1, 20/06536-3)
CLARK, JOSHUA L.; TAYLOR, ALARIC; GEDDIS, AILSA; NEYYAPPADATH, RIFAHATH M.; PISCELLI, BRUNO A.; YU, CIHANG; CORDES, DAVID B.; SLAWIN, ALEXANDRA M. Z.; CORMANICH, RODRIGO A.; GULDIN, STEFAN; et al. Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs. CHEMICAL SCIENCE, v. 12, n. 28, p. 9712-9719, . (18/03910-1, 19/03855-3)
PORT, VINICIUS C.; CORMANICH, RODRIGO A.. There and back again: the role of hyperconjugation in the fluorine gauche effect. Physical Chemistry Chemical Physics, v. 23, n. 32, . (18/03910-1)
SIMOES, LUIS H.; CORMANICH, RODRIGO A.. Challenges in studying steric interactions in highly strained perhalogenated alkanes and silanes. International Journal of Quantum Chemistry, v. 121, n. 21, . (18/03910-1)

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