Please use this identifier to cite or link to this item: http://repositorio.ufla.br/jspui/handle/1/41844
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dc.creatorAndrade, Laize A. F.-
dc.creatorSilla, Josué M.-
dc.creatorFreitas, Matheus P.-
dc.date.accessioned2020-07-12T23:40:37Z-
dc.date.available2020-07-12T23:40:37Z-
dc.date.issued2014-08-25-
dc.identifier.citationANDRADE, L. A. F.; SILLA, J. M.; FREITAS, M. P. The gauche effect is governed by internal hydrogen bond in 2-amino-2-methyl-propanol. Journal of Molecular Structure, [S.l.], v. 1072, p. 203-207, Aug. 2014. DOI: 10.1016/j.molstruc.2014.05.006.pt_BR
dc.identifier.urihttps://www.sciencedirect.com/science/article/abs/pii/S0022286014004657pt_BR
dc.identifier.urihttp://repositorio.ufla.br/jspui/handle/1/41844-
dc.description.abstractThe conformational isomerism of 2-amino-2-methyl-propanol (AMP) was theoretically studied using ab initio and DFT methods, both in the gas phase and implicit solvents. A gauche structure among 13 possible conformers was highly prevalent in the vacuum, nonpolar (cyclohexane) and polar (acetonitrile) solution. Natural bond orbital analysis and the quantum theory of atoms in molecules indicate the appearance of intramolecular hydrogen bond, especially the OH…N interaction, which was found to govern the conformational isomerism and, therefore, the gauche effect in AMP for both the isolated molecule and in solution. Such an interaction has a strong hyperconjugative contribution, as well as the antiperiplanar interactions usually invoked to explain the gauche effect, namely the σCH → σ*CN and σCC → σ*CO interactions, which are stronger than the corresponding σCO → σ*CN and σCN → σ*CO interactions in the anti conformers. Intermolecular hydrogen bond takes place according to an explicit solvent (water) model. For the neat liquid, the gauche conformation is also preferred, according to infrared analysis of the C–O stretching mode, but intermolecular interactions should also be present.pt_BR
dc.languageen_USpt_BR
dc.publisherElsevierpt_BR
dc.rightsrestrictAccesspt_BR
dc.sourceJournal of Molecular Structurept_BR
dc.subjectHydrogen bondpt_BR
dc.subjectGauche effectpt_BR
dc.subjectHyperconjugationpt_BR
dc.subject2-Amino-2-methyl-propanolpt_BR
dc.titleThe gauche effect is governed by internal hydrogen bond in 2-amino-2-methyl-propanolpt_BR
dc.typeArtigopt_BR
Appears in Collections:DQI - Artigos publicados em periódicos

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