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Conformational dynamics of substituted N-acetyl-N-phenylbenzylamines. 1H-DNMR and AM1-MO study

Professor Guidedc.contributor.advisorJullian, Carolina
Authordc.contributor.authorWeiss López, Boris 
Authordc.contributor.authorSaitz Barría, Claudio 
Authordc.contributor.authorPessoa Mahana, Hernán 
Authordc.contributor.authorValderrama, Jaime 
Authordc.contributor.authorAraya Maturana, Ramiro 
Cita de ítemdc.identifier.citationBoletin de la Sociedad Chilena de Quimica, Volumen 46, Issue 3, 2018, Pages 261-269
Abstractdc.description.abstractActivation parameters for the rotation around the methylene-nitrogen single bond found in a series of four 2,2'-disubstituted N-acetyl-N-phenylbenzylamines, dissolved in DMSO-d6, were measured employing the temperature dependence of the 1H-NMR spectrum lineshape between 340 and 400 K. The results are : (I) 2 - [N-acetyl -N- (2-acetamidophenyl) aminomethyl]phenylacetate AG-=79.9±2.0 kJ/mol (370K), AH'=96.2±6.0 kJ/mol and AS'=+45±20 J/Kmol; (II) 2 [N - acetyl - N - (2-acetyloxybenzyl)amino]benzylacetate AG'=82.0±2.0 kJ/mol (370K), AH-=79.1±6.0 kcal/mol and AS'=-8±20 J/Kmol; (III) 2 - [N - Acetyl - N - (2nitrobenzyl)amino]benzylacetate AG'=80.8±2.0 kJ/mol (380K), AH=60.7±6.0 kcal/mol and AS=-53±20 J/Kmol; (IV) 2-[N-Acetyl-N-(2-acetyloxybenzyl)amino]phenylacetate AG-=77.0±2.0 kJ/mol (370K), AH'=65.3±6.0 kJ/mol and AS'=-32±20 J/Kmol. Substitution at positions 2 and 2' with bulky groups appears to be essential to freeze the gauche structure at room temperature and consequently, the main cont
Type of licensedc.rightsAttribution-NonCommercial-NoDerivs 3.0 Chile
Link to Licensedc.rights.uri
Sourcedc.sourceBoletin de la Sociedad Chilena de Quimica
Keywordsdc.subjectConformational dynamics
Títulodc.titleConformational dynamics of substituted N-acetyl-N-phenylbenzylamines. 1H-DNMR and AM1-MO study
Document typedc.typeArtículo de revista
Indexationuchile.indexArtículo de publicación SCOPUS

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