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Abstract:

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.

Registro:

Documento: Artículo
Título:Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations
Autor:Bergero, F.; Alvaro, C.E.S.; Nudelman, N.S.; Ramos de Debiaggi, S.
Filiación:Departamento de Física, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires 1400, 8300 Neuquen, Argentina
Departamento de Química, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires 1400, 8300 Neuquen, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Departamento de Física, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires 1400, 8300 Neuquen, Argentina
Palabras clave:2-Guanidinobenzimidazole; Ab-initio calculations; Aromatic nucleophilic substitution; Hydrogen bonded nucleophiles; Mixed-aggregates
Año:2009
Volumen:896
Número:1-3
Página de inicio:18
Página de fin:24
DOI: http://dx.doi.org/10.1016/j.theochem.2008.10.045
Título revista:Journal of Molecular Structure: THEOCHEM
Título revista abreviado:J. Mol. Struct. THEOCHEM
ISSN:01661280
CODEN:THEOD
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01661280_v896_n1-3_p18_Bergero

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Citas:

---------- APA ----------
Bergero, F., Alvaro, C.E.S., Nudelman, N.S. & Ramos de Debiaggi, S. (2009) . Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations. Journal of Molecular Structure: THEOCHEM, 896(1-3), 18-24.
http://dx.doi.org/10.1016/j.theochem.2008.10.045
---------- CHICAGO ----------
Bergero, F., Alvaro, C.E.S., Nudelman, N.S., Ramos de Debiaggi, S. "Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations" . Journal of Molecular Structure: THEOCHEM 896, no. 1-3 (2009) : 18-24.
http://dx.doi.org/10.1016/j.theochem.2008.10.045
---------- MLA ----------
Bergero, F., Alvaro, C.E.S., Nudelman, N.S., Ramos de Debiaggi, S. "Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations" . Journal of Molecular Structure: THEOCHEM, vol. 896, no. 1-3, 2009, pp. 18-24.
http://dx.doi.org/10.1016/j.theochem.2008.10.045
---------- VANCOUVER ----------
Bergero, F., Alvaro, C.E.S., Nudelman, N.S., Ramos de Debiaggi, S. Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations. J. Mol. Struct. THEOCHEM. 2009;896(1-3):18-24.
http://dx.doi.org/10.1016/j.theochem.2008.10.045