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| Author(s): |
Thaís Mendonça Barbosa
Total Authors: 1
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| Document type: | Master's Dissertation |
| Press: | Campinas, SP. |
| Institution: | Universidade Estadual de Campinas (UNICAMP). Instituto de Química |
| Defense date: | 2014-07-18 |
| Examining board members: |
Roberto Rittner Neto;
Jarbas Magalhães Resende;
Luiz Carlos Dias
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| Advisor: | Roberto Rittner Neto |
| Abstract | |
This work titled: STEREOELECTRONIC INTERACTIONS AND THEIR EFFECTS IN THE CONFORMATIONAL PREFERENCES OF 3-HALO-2-HYDROXY-TETRAHYDROPYRAN (HALO = F, Cl, Br and I) aims to evaluate the effect of stereoelectronic interactions on the conformational stability of halohydrins derived from pyran (3-halo-2-hydroxy-tetrahydropyran halo = F, Cl, Br and I). The study was performed through NMR spectroscopy, supported by electronic structure calculations. The compounds were synthesized, purified and identified by their 1H, 13C, selective TOCSY NMR spectra as well as by their HSQC, COSY and NOESY contour map. The theoretical calculations were performed through Density Functional Theory (DFT) applying B3LYP hybrid functional and also ab inito theory was used applying MP2 method, for both theory aug-cc-pVTZ basis set were used to obtain the geometry and energy for the most stable conformers for the isolated molecule. NBO (natural bond orbitals), QTAIM (Quantum Theory of Atoms in Molecules) and NCI (Non-Covalent Interactions) analysis were applied to allow us to find out which stereoelectronic interactions are responsible by conformational stability. The combined analyses of all these data have shown which are the factors responsible for the conformational preferences of the compounds under study (AU) | |
| FAPESP's process: | 11/14301-7 - Stereoelectronic interactions and their effects in the conformational preferences of 3-halo-2-hydroxy-tetrahydropyran (halo = F, Cl, Br and I) |
| Grantee: | Thaís Mendonça Barbosa |
| Support Opportunities: | Scholarships in Brazil - Master |