Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations

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The role of inter- and intramolecular hydrogen bonding is very important for defining the reactivity of a great diversity of structures. In aromatic nucleophilic substitutions (SNAr) with amines in aprotic solvents, the attendance of hydrogen bond interactions (solute-solute and solute-solvent) has...

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Detalles Bibliográficos
Autor principal: Bergero, Federico Daniel
Otros Autores: Alvaro, Cecilia Elisabeth Silvana, Nudelman, N.S, Ramos de Debiaggi, S.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2009
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Bergero, Federico Daniel 
245 1 0 |a Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations 
260 |c 2009 
270 1 0 |m Ramos de Debiaggi, S.; Departamento de Física, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires 1400, 8300 Neuquen, Argentina; email: ramos@uncoma.edu.ar 
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504 |a Bergero, F., Alvaro, C.E.S., Nudelman, N.S., Ramos de Debiaggi, S., (2006) Anales de la Asociación Física Argentina, 18, p. 52 
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506 |2 openaire  |e Política editorial 
520 3 |a The role of inter- and intramolecular hydrogen bonding is very important for defining the reactivity of a great diversity of structures. In aromatic nucleophilic substitutions (SNAr) with amines in aprotic solvents, the attendance of hydrogen bond interactions (solute-solute and solute-solvent) has been proposed to understand kinetic results. In order to hold up recently reported experimental results on SNAr, in this paper we study structural and electronic properties of the aromatic polyamine 2-guanidinobenzimidazole, the aprotic polar solvent molecule dimethylsulphoxide and their interactions. Semi-empirical and ab-initio density functional theory calculations were performed to investigate, in particular, the possibility of hydrogen bond formation. It is found that 2-guanidinobenzimidazole presents intra- and intermolecular hydrogen bond formation leading to homo 2-GB and mixed solute-solvent dimers; being the latter energetically slightly more favorable than the former one. © 2008 Elsevier B.V. All rights reserved.  |l eng 
536 |a Detalles de la financiación: Universidad Nacional del Litoral, 04-I123-UNCo, 04-I135-UNCo 
536 |a Detalles de la financiación: Financial help from the Universidad Nacional del Comahue grants N° 04-I123-UNCo and 04-I135-UNCo is gratefully acknowledged. 
593 |a Departamento de Física, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires 1400, 8300 Neuquen, Argentina 
593 |a Departamento de Química, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires 1400, 8300 Neuquen, Argentina 
593 |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
593 |a Departamento de Física, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires 1400, 8300 Neuquen, Argentina 
690 1 0 |a 2-GUANIDINOBENZIMIDAZOLE 
690 1 0 |a AB-INITIO CALCULATIONS 
690 1 0 |a AROMATIC NUCLEOPHILIC SUBSTITUTION 
690 1 0 |a HYDROGEN BONDED NUCLEOPHILES 
690 1 0 |a MIXED-AGGREGATES 
700 1 |a Alvaro, Cecilia Elisabeth Silvana 
700 1 |a Nudelman, N.S. 
700 1 |a Ramos de Debiaggi, S. 
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