Stereoelectronic interactions and their effects in the conformational preferences of 3-halo-2-hydroxy-tetrahydropyran (halo = F, Cl, Br and I)

• Grant number: 11/14301-7
• Support Opportunities: Scholarships in Brazil - Master
• Start date: March 01, 2012
• End date: July 31, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Roberto Rittner Neto
• Grantee: Thaís Mendonça Barbosa
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated scholarship(s): 13/08251-2 - NMR characterization of some modified nucleoside bases related to 8-nitroguanine, BE.EP.MS

Abstract

This project involves the study of 3-halo-2-hydroxy-tetrahydropyran (halo = F, Cl, Br and I), through NMR and IR spectroscopies, supported by electronic structure calculations. The compounds will be synthesized and identified by their 1H and 13C NMR spectra. Low temperature 1H NMR experiments will be performed to determine experimentally the conformer population. The theoretical calculations will be performed through Density Funcional Theory (DFT) applying B3LYP hybrid functional and also ab inito theory will be applying using MP2 method, for both theory aug-cc-pVTZ basis set will be applied to obtain geometry and energy for the most stable conformers in the vapor phase. NBO (natural bond orbitals) and QTAIM analysis will be applied to allow us to find out which stereoelectronic interactions are responsible by conformational stability.

Scientific publications

(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)

MYCROFT, CORAL; DAL POGGETTO, GUILHERME; BARBOSA, THAIÏS M.; TORMENA, CLAÏUDIO F.; NILSSON, MATHIAS; MORRIS, GARETH A.; CASTANAR, LAURA. Rapid Measurement of Heteronuclear Coupling Constants in Complex NMR Spectra. Journal of the American Chemical Society, v. 145, n. 36, p. 8-pg., 2023-08-31. (14/12776-6, 11/14301-7, 18/19253-0, 20/10246-0)

SOLHA, DANIELA C.; BARBOSA, THAIS M.; VIESSER, RENAN V.; RITTNER, ROBERTO; TORMENA, CLAUDIO F.. Experimental and Theoretical Studies of Intramolecular Hydrogen Bonding in 3-Hydroxytetrahydropyran: Beyond AIM Analysis. Journal of Physical Chemistry A, v. 118, n. 15, p. 2794-2800, APR 17 2014. (11/17357-3, 11/14301-7, 12/12414-1)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

BARBOSA, Thaís Mendonça. Stereoelectronic interactions on the conformational preferences of 3-halo-2-hydroxytetrahydropyrans (halo = F, Cl, Br and I) through theoretical calculations and NMR spectroscopy. 2014. Master's Dissertation - Universidade Estadual de Campinas (UNICAMP). Instituto de Química Campinas, SP.