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Physicochemical studies of organic molecules : long range interactions and conformational analysis of organofluorine compounds

Rodrigo Antonio Cormanich
Total Authors: 1
Document type: Doctoral Thesis
Institution: Universidade Estadual de Campinas. Instituto de Química
Defense date:
Examining board members:
Jarbas Magalhães Resende; Luiz Alberto Colnago; Rogério Custodio; Paulo José Samenho Moran
Advisor: Roberto Rittner Neto

The present PhD thesis reports physicochemical studies of several organic compounds. In particular, the conformational preferences and the intramolecular interactions of dipeptide models, as the Ac-Gly-NHMe and its fluorinated and Nmethyl derivatives CF3-C(O)-Gly-NHMe and Ac-Gly-N(Me)2, were investigated. Furthermore, the present work studies the physicochemistry of intra- and intermolecular long range interactions in several fluorinated organic compounds, as non-usual C-H···π hydrogen bonds with the solvent and CF···FC interactions. The conformational isomerisms of 2-fluoroethanol, 3-fluoropropanol and 4-fluorobutanol and also the importance of CF···HO hydrogen bonding formation for their conformational isomerisms were investigated. Experimental data from 1H and 19F NMR and infrared spectroscopies in several solvents, as well as from X-ray diffraction of crystalline structures were used. Some fluorinated compounds are not commercial, which were then synthesised and characterised. Moreover, in order to compare and elucidate the experimental results, theoretical chemistry methods were used in several levels, by using DFT functionals with and without dispersion corrections and ab initio methods. In particular, NBO analysis was used to evaluate the contribution of stereoelectronic effects. Long-range interactions were studied by theoretical chemistry topological methods, as the QTAIM, NCI, ELF and DORI. Theoretical calculations of spin-spin coupling constants and frequencies for the isolated structures of these compounds and in the presence of solvent, by considering the IEFPCM implicit solvent model, were also carried out. The results obtained by the experimental and theoretical methods were compared, which provided descriptions of the results that any of them alone could accomplish (AU)

FAPESP's process: 11/01170-1 - Physicochemical studies of organic compounds: long range inractions and conformational analysis of organofluorine compounds.
Grantee:Rodrigo Antonio Cormanich
Support type: Scholarships in Brazil - Doctorate