Aromatic nucleophilic substitution in aprotic solvents using hydrogen-bonded biological amines. Kinetic studies and quantum chemical calculations

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Intermolecular and intramolecular non-bonding interactions play a crucial role in determining physical and biological properties of relevant amines, and we have recently reported that they are also responsible for changing mechanisms in aromatic nucleophilic substitution (ANS) involving amine nucleo...

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Autor principal: Alvaro, Cecilia Elisabeth Silvana
Otros Autores: Bergero, Federico Daniel, Bolcic, F.M, Ramos, S.B, Sbarbati Nudelman, N.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: John Wiley and Sons Ltd 2016
Acceso en línea:Registro en Scopus
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100 1 |a Alvaro, Cecilia Elisabeth Silvana 
245 1 0 |a Aromatic nucleophilic substitution in aprotic solvents using hydrogen-bonded biological amines. Kinetic studies and quantum chemical calculations 
260 |b John Wiley and Sons Ltd  |c 2016 
270 1 0 |m Alvaro, C.E.S.; Depto. de Química, Facultad de Ingeniería, Universidad Nacional del ComahueArgentina; email: silvana_alvaro@hotmail.com 
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506 |2 openaire  |e Política editorial 
520 3 |a Intermolecular and intramolecular non-bonding interactions play a crucial role in determining physical and biological properties of relevant amines, and we have recently reported that they are also responsible for changing mechanisms in aromatic nucleophilic substitution (ANS) involving amine nucleophiles, when they are carried out in solvents of low permittivity. The present work describes ANS in toluene with a series of biological amines that can set specific hydrogen bonding (H bonding) interactions due to their special molecular structures. Kinetic studies of ANS with 2-amino-5-guanidinopentanoic acid (arginine), (4-aminobutyl)guanidine (agmatine), 2,6-diaminohexanoic acid (lysine) and 3,4-dihydroxyphenethylamine (dopamine) towards 1-chloro-2,4-dinitrobenzene in toluene are reported. The kinetic results are compared with those obtained with 2-guanidinobenzimidazole and 2-(1H-imidazole-4-yl)ethanamine (histamine); both amines form intramolecular H bonds. The special types of H bonding were also investigated by ab initio density functional theory calculations, at the B3LYP/6-31++G(d,p) level, including counterpoise corrections to account for basis set superposition errors and solvent effects at the polarized continuum model level. Copyright © 2015 John Wiley & Sons, Ltd. Copyright © 2015 John Wiley & Sons, Ltd.  |l eng 
593 |a Depto. de Química, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires, Neuquén 1400 (8300), Argentina 
593 |a Instituto de Investigaciones y Desarrollo en Ingeniería de Procesos, Biotecnología y Energías Alternativas (PROBIEN), CONICET – Universidad Nacional del Comahue, Neuquén, (8300), Argentina 
593 |a Depto. de Física, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires, Neuquén 1400 (8300), Argentina 
593 |a Facultad de Ciencias Médicas, Universidad Nacional del Comahue, Cipolletti, Río Negro (8324), Argentina 
593 |a Depto. Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Buenos Aires, (1428), Argentina 
690 1 0 |a APROTIC SOLVENTS 
690 1 0 |a AROMATIC NUCLEOPHILIC SUBSTITUTION 
690 1 0 |a BIOLOGICAL AMINES 
690 1 0 |a DIMER NUCLEOPHILE MECHANISM 
690 1 0 |a HYDROGEN BONDING 
690 1 0 |a AMINES 
690 1 0 |a AMINO ACIDS 
690 1 0 |a AROMATIZATION 
690 1 0 |a CALCULATIONS 
690 1 0 |a CONTINUUM MECHANICS 
690 1 0 |a COPYRIGHTS 
690 1 0 |a DENSITY FUNCTIONAL THEORY 
690 1 0 |a DIMERS 
690 1 0 |a HYDROGEN 
690 1 0 |a KINETIC THEORY 
690 1 0 |a KINETICS 
690 1 0 |a NUCLEOPHILES 
690 1 0 |a QUANTUM CHEMISTRY 
690 1 0 |a SOLVENTS 
690 1 0 |a TOLUENE 
690 1 0 |a 1-CHLORO-2 , 4-DINITROBENZENE 
690 1 0 |a AB INITIO DENSITY FUNCTIONAL THEORIES (DFT) 
690 1 0 |a APROTIC SOLVENTS 
690 1 0 |a AROMATIC NUCLEOPHILIC SUBSTITUTION 
690 1 0 |a BASIS SET SUPERPOSITION ERRORS 
690 1 0 |a DIMER NUCLEOPHILE MECHANISMS 
690 1 0 |a QUANTUM CHEMICAL CALCULATIONS 
690 1 0 |a SPECIFIC HYDROGEN BONDINGS 
690 1 0 |a HYDROGEN BONDS 
700 1 |a Bergero, Federico Daniel 
700 1 |a Bolcic, F.M. 
700 1 |a Ramos, S.B. 
700 1 |a Sbarbati Nudelman, N. 
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