A theoretical and experimental 1H NMR spectroscopy study of the stereoelectronic interactions that rule the conformational energies of alanine and valine methyl ester

dc.creatorCormanich, RA
dc.creatorDucati, LC
dc.creatorTormena, CF
dc.creatorRittner, R
dc.date2013
dc.dateOCT
dc.date2014-07-30T13:43:04Z
dc.date2015-11-26T17:37:48Z
dc.date2014-07-30T13:43:04Z
dc.date2015-11-26T17:37:48Z
dc.date.accessioned2018-03-29T00:19:28Z
dc.date.available2018-03-29T00:19:28Z
dc.identifierJournal Of Physical Organic Chemistry. Wiley-blackwell, v. 26, n. 10, n. 849, n. 857, 2013.
dc.identifier0894-3230
dc.identifier1099-1395
dc.identifierWOS:000325936700013
dc.identifier10.1002/poc.3180
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/53893
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/53893
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1286054
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionAmino acids exhibit a bipolar zwitterionic structure (+H3N-CHR-COO-) in solution; hence, conformational studies of these compounds have been limited to the gas phase. The conformational preferences of amino acids have been widely attributed to intramolecular hydrogen bonding, despite steric and hyperconjugative effects. In this work, we propose the conformational study of alanine and valine methyl esters, which do not show zwitterionic structures in solution, by1H NMR and theoretical calculations. The 3JHH spin-spin coupling constants and theoretical calculations were found to be in agreement, showing that the interplay between steric hindrance and hyperconjugation is the forces that are responsible for determining the conformational preferences of alanine and valine methyl esters. Copyright (c) 2013 John Wiley & Sons, Ltd.
dc.description26
dc.description10
dc.description849
dc.description857
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.languageen
dc.publisherWiley-blackwell
dc.publisherHoboken
dc.publisherEUA
dc.relationJournal Of Physical Organic Chemistry
dc.relationJ. Phys. Org. Chem.
dc.rightsfechado
dc.rightshttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dc.sourceWeb of Science
dc.subjectconformational analysis
dc.subjectamino acids
dc.subjectmethyl ester derivatives
dc.subjectintramolecular hydrogen bonding
dc.subjectstereoelectronic effects
dc.subjectGlycine-water Complex
dc.subjectAmino-acids
dc.subjectGas-phase
dc.subjectFt-ir
dc.subjectCrystal-structure
dc.subjectMatrix-isolation
dc.subjectL-phenylalanine
dc.subjectHydrogen-bonds
dc.subjectConformers
dc.subjectShape
dc.titleA theoretical and experimental 1H NMR spectroscopy study of the stereoelectronic interactions that rule the conformational energies of alanine and valine methyl ester
dc.typeArtículos de revistas


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