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Conformational Analysis of Some Aliphatic Esters Bearing a Nitrogen Atom as a Substituent

Grant number: 16/24109-0
Support type:Regular Research Grants
Duration: May 01, 2017 - April 30, 2019
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Roberto Rittner Neto
Grantee:Roberto Rittner Neto
Home Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil


The conformational analysis of some esters with a nitrogen atom as a substituent, through 1H and 13C NMR spectroscopy, infrared spectroscopy and theoretical calculations. The theoretical calculations will be performed at MP2 and DFT level of theory, using several basis sets, and including Zero-Point corrections (ZPE), available in the Gaussian-09 for the determination of the energies and geometries of the most stable conformers in the isolated form and through the IEF-PCM model to simulate the solvation effects in the conformational isomerism of the proposed compounds. The analysis of the carbonyl band (fundamental and 1st overtone) in several solvents will give the populations of the more stable rotamers in solution. The NMR spectra will provide JHH coupling constants, geminal and vicinal, involving the CH and CH2 groups, in solution, which can indicate changes in conformer populations according to the permittivity of the solvent. Values obtained from theoretical calculations of the carbonyl stretching vibration and of the coupling constants, in the studied solvents, will be compared with the experimental data in the assessment of the populations of the more stable conformers. Lastly, the contributions of the classical intramolecular interactions (steric and electrostatic) and quantum interactions (hyperconjugation) to stabilize a given conformer will be evaluated through topological analyses from the Quantum Theory of Atoms in Molecules (QTAIM) and Non Covalent Interactions (NCI), and also the Natural Bond Orbitals (NBO) analysis. A joint analysis with these techniques may allow unequivocally the main effects which are responsible for the conformer stabilities of these important systems. (AU)

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Scientific publications (7)
(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)
BARBOSA, THAIS M.; CASTANAR, LAURA; MOUTZOURI, PINELOPI; NILSSON, MATHIAS; MORRIS, GARETH A.; RITTNER, ROBERTO; TORMENA, CLAUDIO F. Improving the Sensitivity of FESTA Methods for the Analysis of Fluorinated Mixtures. Analytical Chemistry, v. 92, n. 2, p. 2224-2228, JAN 21 2020. Web of Science Citations: 0.
FRANCISCO, CAMILA B.; FERNANDES, CLEVERTON S.; DE MELO, ULISSES Z.; RITTNER, ROBERTO; GAUZE, GISELE F.; BASSO, ERNANI A. Strong hyperconjugative interactions limit solvent and substituent influence on conformational equilibrium: the case of cis-2-halocyclohexylamines. Beilstein Journal of Organic Chemistry, v. 15, p. 818-829, APR 1 2019. Web of Science Citations: 0.
BRAGA, CAROLYNE B.; SILVA, WESLLEY G. D. P.; RITTNER, ROBERTO. Conformational preferences of N-acetyl-N-methylprolineamide in different media: a H-1 NMR and theoretical investigation. NEW JOURNAL OF CHEMISTRY, v. 43, n. 4, p. 1757-1763, JAN 28 2019. Web of Science Citations: 2.
BARBOSA, THAIS M.; VIESSER, RENAN V.; MARTINS, LUCAS G.; RITTNER, ROBERTO; TORMENA, CLAUDIO F. The Antagonist Effect of Nitrogen Lone Pair: (3)J(HF) versus (5)J(HF). ChemPhysChem, v. 19, n. 11, p. 1358-1362, JUN 5 2018. Web of Science Citations: 1.
SIVA, WESLLEY G. D. P.; TORMENA, CLAUDIO F.; RITTNER, ROBERTO. Revealing the Conformational Preferences of Proteinogenic Glutamic Acid Derivatives in Solution by H-1 NMR Spectroscopy and Theoretical Calculations. Journal of Physical Chemistry A, v. 122, n. 18, p. 4555-4561, MAY 10 2018. Web of Science Citations: 2.
CASTANAR, LAURA; MOUTZOURI, PINELOPI; BARBOSA, THAIS M.; TORMENA, CLAUDIO F.; RITTNER, ROBERTO; PHILLIPS, ANDREW R.; COOMBES, STEVEN R.; NILSSON, MATHIAS; MORRIS, GARETH A. FESTA: An Efficient Nuclear Magnetic Resonance Approach for the Structural Analysis of Mixtures Containing Fluorinated Species. Analytical Chemistry, v. 90, n. 8, p. 5445-5450, APR 17 2018. Web of Science Citations: 2.
KARAS, LUCAS J.; BATISTA, PATRICK R.; VIESSER, RENAN V.; TORMENA, CLAUDIO F.; RITTNER, ROBERTO; DE OLIVEIRA, PAULO R. Trends of intramolecular hydrogen bonding in substituted alcohols: a deeper investigation. Physical Chemistry Chemical Physics, v. 19, n. 25, p. 16904-16913, JUL 7 2017. Web of Science Citations: 14.

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