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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Experimental and Theoretical Studies of Intramolecular Hydrogen Bonding in 3-Hydroxytetrahydropyran: Beyond AIM Analysis

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Solha, Daniela C. [1] ; Barbosa, Thais M. [1] ; Viesser, Renan V. [1] ; Rittner, Roberto [1] ; Tormena, Claudio F. [1]
Total Authors: 5
[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Journal of Physical Chemistry A; v. 118, n. 15, p. 2794-2800, APR 17 2014.
Web of Science Citations: 13

The conformational preferences of 3-hydroxytetrahydropyran (1) were evaluated using infrared and nuclear magnetic resonance spectroscopic data in solvents of different polarities. Theoretical calculations in the isolated phase and including the solvent effect were performed, showing that the most stable conformations for compound I are those containing the substituent in the axial and equatorial orientations. The axial conformation is more stable in the isolated phase and in a nonpolar solvent, while the equatorial conformation is more stable than the axial in polar media. The occurrence of intramolecular hydrogen-bonded O-H center dot center dot center dot O in the axial conformer was detected from infrared spectra in a nonpolar solvent at different concentrations. Our attempt to evaluate this interaction using population natural bond orbital and topological quantum theory of atoms in molecules analyses failed, but topological noncovalent interaction analysis was capable of characterizing it. (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 type: Scholarships in Brazil - Master
FAPESP's process: 11/17357-3 - Relationship between molecular electronic structure, NMR parameters and conformational stability
Grantee:Claudio Francisco Tormena
Support type: Regular Research Grants
FAPESP's process: 12/12414-1 - Relationship between molecular electronic structure and heavy atom effect on 13C NMR chemical shift
Grantee:Renan Vidal Viesser
Support type: Scholarships in Brazil - Doctorate