Inter- and intramolecular hydrogen bonds in polyamines: Variable-concentration 1H-NMR studies

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Inter- and intramolecular hydrogen bonding play an important role in determining the arrangement, physical properties, and reactivity of a great diversity of structures in chemical and biological systems. Several aromatic nucleophilic substitutions (ANS) in nonpolar aprotic, (non-HBD), solvents rece...

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Autor principal: Nudelman, N.S
Otros Autores: Alvaro, Cecilia Elisabeth Silvana
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2011
Acceso en línea:Registro en Scopus
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100 1 |a Nudelman, N.S. 
245 1 0 |a Inter- and intramolecular hydrogen bonds in polyamines: Variable-concentration 1H-NMR studies 
260 |c 2011 
270 1 0 |m Nudelman, N.S.; Departamento de Química Orgánica, Facultad de Ciencias Exactas, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: nudelman@qo.fcen.uba.ar 
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506 |2 openaire  |e Política editorial 
520 3 |a Inter- and intramolecular hydrogen bonding play an important role in determining the arrangement, physical properties, and reactivity of a great diversity of structures in chemical and biological systems. Several aromatic nucleophilic substitutions (ANS) in nonpolar aprotic, (non-HBD), solvents recently studied in our laboratory have demonstrated the importance of self-association of amines by hydrogen-bond interactions. In this paper, we describe 1H-NMR studies carried out at room temperature on bi- and polyfunctionalized amines, namely: N-(3-amino-1-propyl)morpholine (3-APMo), histamine, 2-guanidinobenzimidazole (2-GB), 1,2-diaminoethane (EDA), 3-dimethylamino-l-propylamine (DMPA), and 1-(2-aminoethyl)piperidine (2-AEPip). By 1H-NMR measurements of amine solutions at variable concentrations we have shown that 3-APMo, histamine and 2-GB are able to form a six-membered ring by intramolecular hydrogen bonding, while EDA, DMPA, and 2-AEPip form dimers by intermolecular hydrogen bonds. Likewise, variable concentration 1H-NMR studies allowed estimation of the corresponding equilibrium constants for the dimerization. These results are correlated with experimental kinetic results of ANS, confirming hereto the relevance of the "dimer mechanism" in reactions involving these amines. Copyright © 2011 John Wiley & Sons, Ltd.  |l eng 
593 |a Departamento de Química Orgánica, Facultad de Ciencias Exactas, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
593 |a Departamento de Química, Facultad de Ingeniería, Universidad Nacional Del Comahue, Buenos Aires 1400, 8300 Neuquén, Argentina 
690 1 0 |a 1H-NMR STUDIES ON AMINE SOLUTIONS 
690 1 0 |a ANS IN NON-HBD SOLVENTS 
690 1 0 |a DIMER NUCLEOPHILE MECHANISM 
690 1 0 |a DIMERIZATION EQUILIBRIUM CONSTANTS 
690 1 0 |a HYDROGEN-BONDED NUCLEOPHILES 
690 1 0 |a HYDROGEN-BONDING EFFECTS ON 1H-NMR 
690 1 0 |a AMINE SOLUTIONS 
690 1 0 |a ANS IN NON-HBD SOLVENTS 
690 1 0 |a DIMER NUCLEOPHILE MECHANISM 
690 1 0 |a HYDROGEN-BONDED NUCLEOPHILES 
690 1 0 |a HYDROGEN-BONDING EFFECTS 
690 1 0 |a AMINES 
690 1 0 |a ASSOCIATION REACTIONS 
690 1 0 |a DIMERIZATION 
690 1 0 |a DIMERS 
690 1 0 |a EQUILIBRIUM CONSTANTS 
690 1 0 |a HYDROGEN 
690 1 0 |a NUCLEOPHILES 
690 1 0 |a HYDROGEN BONDS 
700 1 |a Alvaro, Cecilia Elisabeth Silvana 
773 0 |d 2011  |g v. 24  |h pp. 1067-1071  |k n. 11  |p J Phys Org Chem  |x 08943230  |w (AR-BaUEN)CENRE-576  |t Journal of Physical Organic Chemistry 
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856 4 0 |u https://doi.org/10.1002/poc.1832  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_08943230_v24_n11_p1067_Nudelman  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v24_n11_p1067_Nudelman  |y Registro en la Biblioteca Digital 
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963 |a VARI 
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