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

Autor(es)

Solha, Daniela C. ^[1] ; Barbosa, Thais M. ^[1] ; Viesser, Renan V. ^[1] ; Rittner, Roberto ^[1] ; Tormena, Claudio F. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Physical Chemistry A; v. 118, n. 15, p. 2794-2800, APR 17 2014.
• Citações Web of Science: 13

Resumo

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)

• Processo FAPESP: 11/17357-3 - Estrutura eletrônica molecular e sua relação com os parâmetros de RMN e a estabilidade conformacional
• Beneficiário: Claudio Francisco Tormena
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 11/14301-7 - Interações estereoeletrônicas e seus efeitos na preferência conformacional de 3-halo-2-hidroxi-tetraidropirano (halo = F, Cl, Br e I)
• Beneficiário: Thaís Mendonça Barbosa
• Modalidade de apoio: Bolsas no Brasil - Mestrado
• Processo FAPESP: 12/12414-1 - Estrutura eletrônica molecular e sua relação com o efeito do átomo pesado em RMN de 13C
• Beneficiário: Renan Vidal Viesser
• Modalidade de apoio: Bolsas no Brasil - Doutorado