Repositorio Institucional
Repositorio Institucional
CONICET Digital
  • Inicio
  • EXPLORAR
    • AUTORES
    • DISCIPLINAS
    • COMUNIDADES
  • Estadísticas
  • Novedades
    • Noticias
    • Boletines
  • Ayuda
    • General
    • Datos de investigación
  • Acerca de
    • CONICET Digital
    • Equipo
    • Red Federal
  • Contacto
JavaScript is disabled for your browser. Some features of this site may not work without it.
  • INFORMACIÓN GENERAL
  • RESUMEN
  • ESTADISTICAS
 
Artículo

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

Alvaro, Cecilia E. Silvana; Bergero, FedericoIcon ; Bolcic, Federico MartinIcon ; Ramos, Susana BeatrizIcon ; Sbarbati, Norma EthelIcon
Fecha de publicación: 12/2015
Editorial: Wiley
Revista: Journal Of Physical Organic Chemistry
ISSN: 0894-3230
e-ISSN: 1099-1395
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Química Orgánica

Resumen

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.
Palabras clave: Aprotic Solvents , Aromatic Nucleophilic Substitution , Biological Amines , Dimer Nucleophile Mechanism , Hydrogen Bonding
Ver el registro completo
 
Archivos asociados
Thumbnail
 
Tamaño: 1.691Mb
Formato: PDF
.
Descargar
Licencia
info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/11694
URL: http://onlinelibrary.wiley.com/doi/10.1002/poc.3519/abstract
DOI: http://dx.doi.org/10.1002/poc.3519
Colecciones
Articulos(PROBIEN)
Articulos de INST. DE INVESTIGACION Y DES. EN ING. DE PROCESOS, BIOTECNOLOGIA Y ENERGIAS ALTERNATIVAS
Citación
Alvaro, Cecilia E. Silvana; Bergero, Federico; Bolcic, Federico Martin; Ramos, Susana Beatriz; Sbarbati, Norma Ethel; Aromatic nucleophilic substitution in aprotic solvents using hydrogen-bonded biological amines; kinetics studies and quantum chemical calculations; Wiley; Journal Of Physical Organic Chemistry; 29; 11; 12-2015; 565-573
Compartir
Altmétricas
 

Enviar por e-mail
Separar cada destinatario (hasta 5) con punto y coma.
  • Facebook
  • X Conicet Digital
  • Instagram
  • YouTube
  • Sound Cloud
  • LinkedIn

Los contenidos del CONICET están licenciados bajo Creative Commons Reconocimiento 2.5 Argentina License

https://www.conicet.gov.ar/ - CONICET

Inicio

Explorar

  • Autores
  • Disciplinas
  • Comunidades

Estadísticas

Novedades

  • Noticias
  • Boletines

Ayuda

Acerca de

  • CONICET Digital
  • Equipo
  • Red Federal

Contacto

Godoy Cruz 2290 (C1425FQB) CABA – República Argentina – Tel: +5411 4899-5400 repositorio@conicet.gov.ar
TÉRMINOS Y CONDICIONES