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Abstract:

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.

Registro:

Documento: Artículo
Título:Aromatic nucleophilic substitution in aprotic solvents using hydrogen-bonded biological amines. Kinetic studies and quantum chemical calculations
Autor:Alvaro, C.E.S.; Bergero, F.D.; Bolcic, F.M.; Ramos, S.B.; Sbarbati Nudelman, N.
Filiación:Depto. de Química, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires, Neuquén 1400 (8300), Argentina
Instituto de Investigaciones y Desarrollo en Ingeniería de Procesos, Biotecnología y Energías Alternativas (PROBIEN), CONICET – Universidad Nacional del Comahue, Neuquén, (8300), Argentina
Depto. de Física, Facultad de Ingeniería, Universidad Nacional del Comahue, Buenos Aires, Neuquén 1400 (8300), Argentina
Facultad de Ciencias Médicas, Universidad Nacional del Comahue, Cipolletti, Río Negro (8324), Argentina
Depto. Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Buenos Aires, (1428), Argentina
Palabras clave:aprotic solvents; aromatic nucleophilic substitution; biological amines; dimer nucleophile mechanism; hydrogen bonding; Amines; Amino acids; Aromatization; Calculations; Continuum mechanics; Copyrights; Density functional theory; Dimers; Hydrogen; Kinetic theory; Kinetics; Nucleophiles; Quantum chemistry; Solvents; Toluene; 1-chloro-2 , 4-dinitrobenzene; Ab initio density functional theories (DFT); Aprotic solvents; Aromatic nucleophilic substitution; Basis set superposition errors; Dimer nucleophile mechanisms; Quantum chemical calculations; Specific hydrogen bondings; Hydrogen bonds
Año:2016
Volumen:29
Número:11
Página de inicio:565
Página de fin:573
DOI: http://dx.doi.org/10.1002/poc.3519
Título revista:Journal of Physical Organic Chemistry
Título revista abreviado:J Phys Org Chem
ISSN:08943230
CODEN:JPOCE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v29_n11_p565_Alvaro

Referencias:

  • Ormazabal-Toledo, R., Santos, J.G., Ríos, P., Castro, E.A., Campodonico, P.R., Contreras, R., (2013) J. Phys. Chem., 117, pp. 5908-5915
  • Nogadry, T., Weaver, D.F., (2005) Medicinal Chemistry: A Molecular and Biochemical Approach, , 3rd edn., Oxford University Press, Inc, New York
  • Ribeiro, R.F., Marenich, A.V., Cramer, C.J., Truhlar, D.G., (2011) Phys. Chem. Chem. Phys., 13, pp. 10908-10922
  • Arunan, E., Desiraju, G.R., Klein, R.A., Sadlej, J., Scheiner, S., Alkorta, I., Clary, D.C., Nesbitt, D.J., (2011) Pure Appl. Chem., 83 (8), pp. 1637-1641
  • Alvaro, C.E.S., Nudelman, N.S., (2011) Trends in Org. Chem., 15, pp. 95-107. , and references therein
  • Nudelman, N.S., ANS reactions of amines in aprotic solvents (1996) The Chemistry of Amino, Nitroso, Nitro and Related Groups, , in, (Eds, S. Patai,), Supplement F2,, John Wiley & Sons, Ltd, London, UK
  • Nudelman, N.S., Alvaro, C.E.S., (2011) J. Phys. Org. Chem., 24 (11), pp. 1067-1071
  • Terrier, F., (2013) Modern Nucleophilic Aromatic Substitution, , 1st edn., Wiley-VCH Verlag GmbH & Co, Weinheim, Germany
  • Crampton, M.R., Nucleophilic aromatic substitution (2012) Organic Reaction Mechanisms Series, , in, (Eds, A. C. Knipe, J. Wiley & Sons, Inc, Hoboken, NJ, USA
  • Drapeau, M.P., Ollevier, T., Taillefer, M., (2014) Chem. Eur. J., 20, pp. 5231-5236
  • Senger, N.A., Bo, B., Cheng, Q., Keeffe, J.R., Gronert, S., Wu, W., (2012) J. Org. Chem., 77, pp. 9535-9540
  • Ormazabal-Toledo, R., Contreras, R., Campodonico, P.R., (2013) J. Org. Chem., 78, pp. 1091-1097
  • Gillham, R.W., (1993) U.S. Patent 5266213, , Nov. 30,, references therein
  • Rains, R.K., (1997) U.S. Patent 5608111, , March 4
  • Alvaro, C.E.S., Nudelman, N.S., (2010) Int. J. Chem. Kinet., 42 (12), pp. 735-742
  • Nudelman, N.S., Palleros, D., (1983) J. Org. Chem., 48 (10), pp. 1613-1617
  • Nudelman, N.S., Montserrat, J., (1990) J. Chem. Soc. Perkin Trans., 2, pp. 1073-1076
  • Nudelman, N.S., (1989) J. Phys. Org. Chem., 2, pp. 1-9
  • Alvaro, C.E.S., Nudelman, N.S., (2005) J. Phys. Org. Chem., 18, pp. 880-885. , a
  • Alvaro, C.E.S., Nudelman, N.S., (2003) ARKIVOC, 10, pp. 95-106. , b
  • Nudelman, N.S., Alvaro, C.E.S., Yankelevich, J.S., (1997) J. Chem. Soc. Perkin Trans., 2, pp. 2125-2130. , c
  • Alvaro, C.E.S., Nudelman, N.S., (2013) Phys. Chem. Special Issue: Chemical Kinetics, 3 (2), pp. 39-47
  • Alvaro, C.E.S., Ayala, A.D., Nudelman, N.S., (2011) J. Phys. Org. Chem., 24 (2), pp. 101-109
  • Parr, R.G., Yang, D., (1989) Density-Functional Theory of Atoms and Molecules, , Oxford University Press, New York
  • Becke, A.D., (1993) J. Chem. Phys., 98 (7), pp. 5648-5652. , a
  • Lee, C., Yang, C.W., Parr, R.G., (1988) Phys. Rev. B, 37, pp. 785-793. , b
  • Schwöbel, J., Ebert, R.-U., Kühne, R., Schürmann, G., (2009) J. Chem. Inf. Model., 49, pp. 956-962
  • Bergero, F.D., Alvaro, C.E.S., Nudelman, N.S., Ramos de Debiaggi, S., (2013) J. Argent. Chem. Soc., 100, pp. 35-47
  • Lide, D.R., Physical constants of organic compounds (2005) CRC Handbook of Chemistry and Physics, , (Ed),, in, CRC Press, Boca Raton, FL
  • Andrade-López, N., Ariza-Castolo, A., Contreras, R., Vasquez-Olmos, A., Barba Behrens, H., Tlahuext, H., (1997) Heteroatom Chem., 8, pp. 397-410
  • Nudelman, N.S., Marder, M., Gurevich, A., (1993) J. Chem. Soc. Perkin Trans., 2, pp. 229-233
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Fox, D.J., (2009) Gaussian 09, Revision A.1, , Gaussian, Inc., Wallingford CT
  • Dewar, M.S.J., Zoebisch, E.G., Healy, R.F., Stewart, J.P., (1985) J. Am. Chem. Soc., 107, pp. 3902-3909
  • Levine, I.N., (2001) Química Cuántica, , 5th edn., Pearson Educación S. A, Madrid
  • Boys, S.F., Bernardi, F., Calculation of small molecular interactions by differences of separate total energies – some procedures with reduced errors (1970) Mol. Phys., 19, pp. 553-556
  • Thanthiriwatte, K.S., Hohenstein, E.G., Burns, L.A., Sherrill, C.D., (2011) J. Chem. Theory Comput., 7, pp. 88-96
  • Su, P., Wu, J., Gu, J., Wu, W., Shaik, S., Hiberty, P.C., (2011) J. Chem. Theory Comput., 7, pp. 121-130
  • Krishtal, A., Geldof, D., Vanommeslaeghe, K., Van Alsenoy, C., Geerlings, P., (2012) J. Chem. Theory Comput., 8, pp. 125-134
  • Scherrer, A., Verschinin, V., Sebastiani, D., (2012) J. Chem. Theory Comput., 8, pp. 106-111
  • Metcalfe, W.K., Simmie, J.M., Curran, H.J., (2010) J. Phys. Chem. A, 114 (17), pp. 5478-5484
  • Hughes, T.F., Friesner, R.A., (2011) J. Chem. Theory Comput., 7, pp. 19-32
  • Tomasi, J., Mennucci, B., Cammi, R., (2005) Chem. Rev., 105 (8), pp. 2999-3093
  • Marenich, A.V., Cramer, C.J., Truhlar, D.G., (2009) J. Phys. Chem. B, 113, pp. 6378-6396
  • Parthasarathi, R., Subramanian, V., Characterization of hydrogen bonding: from Van der Waals interactions to covalency (2006) Hydrogen Bonding – New Insights, , in, (Eds, S. J. Grabowski, Springer, Netherlands
  • Bader, R.F.W., (1991) Chem. Rev., 91 (5), pp. 893-928
  • Lu, T., Chen, F., Multiwfn: a multifunctional wavefunction analyzer (2012) J. Comput. Chem., 33, pp. 580-592
  • Parthasarathi, R., Subramanian, V., Sathyamurthy, N., (2006) J. Phys. Chem. A, 110 (10), pp. 3349-3351
  • Ritchie, C.D., Sawada, M., Nucleophilicity (1987) Advances in Chemistry Series, , in, (Edss, J. M. Harris, S. P. McManus, Nr. 215),, A.C.S., Washington, DC
  • Bergero, F.D., Alvaro, C.E.S., Nudelman, N.S., Ramos de Debiaggi, S., (2009) J. Mol. Struct. (Theochem), 896, pp. 18-24
  • Babatunde, A.I., Nwaoduah, P.P., Ogunbona, O.A., (2005) J. Sci. Res. Dev., 10, pp. 65-72
  • Babatunde, A.I., (2010) J. Sci. Res. Dev., 12, pp. 152-160
  • Babatunde, A.I., Olusegun, A.M., Isanbor, C., (2013) Adv. Appl. Sci. Res., 4 (4), pp. 266-273
  • Ayeridan, A., Bankole, T.O., Hirst, J., Onyido, I., (1977) J. Chem. Soc. Perkin Trans, 2, pp. 597-603. , a
  • Hirst, J., (1994) J. Phys. Org. Chem., 7, pp. 68-74. , b
  • Ford, S.J., McIntyre, G.J., Johnson, M.R., Radosavljević Evans, I., (2013) Cryst. Eng. Comm., 15, pp. 7576-7582

Citas:

---------- APA ----------
Alvaro, C.E.S., Bergero, F.D., Bolcic, F.M., Ramos, S.B. & Sbarbati Nudelman, N. (2016) . Aromatic nucleophilic substitution in aprotic solvents using hydrogen-bonded biological amines. Kinetic studies and quantum chemical calculations. Journal of Physical Organic Chemistry, 29(11), 565-573.
http://dx.doi.org/10.1002/poc.3519
---------- CHICAGO ----------
Alvaro, C.E.S., Bergero, F.D., Bolcic, F.M., Ramos, S.B., Sbarbati Nudelman, N. "Aromatic nucleophilic substitution in aprotic solvents using hydrogen-bonded biological amines. Kinetic studies and quantum chemical calculations" . Journal of Physical Organic Chemistry 29, no. 11 (2016) : 565-573.
http://dx.doi.org/10.1002/poc.3519
---------- MLA ----------
Alvaro, C.E.S., Bergero, F.D., Bolcic, F.M., Ramos, S.B., Sbarbati Nudelman, N. "Aromatic nucleophilic substitution in aprotic solvents using hydrogen-bonded biological amines. Kinetic studies and quantum chemical calculations" . Journal of Physical Organic Chemistry, vol. 29, no. 11, 2016, pp. 565-573.
http://dx.doi.org/10.1002/poc.3519
---------- VANCOUVER ----------
Alvaro, C.E.S., Bergero, F.D., Bolcic, F.M., Ramos, S.B., Sbarbati Nudelman, N. Aromatic nucleophilic substitution in aprotic solvents using hydrogen-bonded biological amines. Kinetic studies and quantum chemical calculations. J Phys Org Chem. 2016;29(11):565-573.
http://dx.doi.org/10.1002/poc.3519