Artículo

Dávalos, J.Z.; Lima, C.F.R.A.C.; Silva, A.M.S.; Santos, L.M.N.B.F.; Erra-Balsells, R.; Salum, M.L. "Energetics of neutral and deprotonated (Z)-cinnamic acid" (2016) Journal of Chemical Thermodynamics. 95:195-201
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Abstract:

We have performed a study of structural, thermochemical and thermophysical properties of the (Z)-cinnamic acid neutral molecule and its corresponding oxyanion (formed by deprotonation of the carboxylic group). The thermophysical study (heat capacities, temperature and enthalpy of fusion) was made by DSC. The following intrinsic (gas-phase) thermochemical magnitudes have been experimentally determined: (i) standard enthalpy of formation, at T = 298.15 K, of the neutral molecule, ΔfHm0(g) = (-215.5 ± 3.2) kJ · mol-1, by combustion calorimetry and by the Knudsen effusion technique, (ii) deprotonation enthalpy, ΔacidH0(g) = (1416.4 ± 8.8) kJ · mol-1 and acidity, GA = (1386.7 ± 8.8) kJ · mol-1, by the EKM method using ESI-TQ Mass Spectrometry. From these results we have also derived the enthalpy of formation of the oxyanion, ΔfHm0(oxyanion, g) = (-303.5 ± 9.4) kJ · mol-1. A computational study, through density functional calculations at the B3LYP/6-311++G(d,p) level of theory, was used to check the good consistency of the experimental results. The global results show that (Z)-cinnamic acid is significantly less stable than the corresponding (E)-isomer, which can be related to the greater acidity of the (Z)-form found in both the gas and aqueous solution phases. © 2015 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Energetics of neutral and deprotonated (Z)-cinnamic acid
Autor:Dávalos, J.Z.; Lima, C.F.R.A.C.; Silva, A.M.S.; Santos, L.M.N.B.F.; Erra-Balsells, R.; Salum, M.L.
Filiación:Instituto de Quimica-Fisica rocasolano, CSIC, Serrano 119, Madrid, 28006, Spain
CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Buenos Aires, 1428, Argentina
Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade Do Porto, Porto, P-4169-007, Portugal
Department of Chemistry and QOPNA, University of Aveiro, Aveiro, P-3810-193, Portugal
Palabras clave:(Z)-cinnamic acid; B3LYP; EKM; Enthalpies of formation; G3; G4; Gas-phase acidity; Computation theory; Density functional theory; Gases; Mass spectrometry; Molecules; Positive ions; Solutions; Thermodynamic properties; B3LYP; Cinnamic acids; EKM; Enthalpies of formation; G3; G4; Gas-phase acidities; Enthalpy
Año:2016
Volumen:95
Página de inicio:195
Página de fin:201
DOI: http://dx.doi.org/10.1016/j.jct.2015.12.014
Título revista:Journal of Chemical Thermodynamics
Título revista abreviado:J Chem Thermodyn
ISSN:00219614
CODEN:JCTDA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00219614_v95_n_p195_Davalos

Referencias:

  • Taiz, L., Zeiger, E., (1998) Plant Physiology, , second ed. Sinauer Associated Inc. Pub
  • Buchanan, B.B., Gruissem, W., Jones, R.L., (2000) Biochemistry & Molecular Biology of Plants, , American Society of Plant Physiologist Rockville (Chapter 24, p. 1286)
  • Dixon, R.A., (2001) Nature, 411, pp. 843-847
  • Humphreys, J.M., Chapple, C., (2002) Curr. Opin. Plant Biol., 5, pp. 224-229
  • Sova, M., (2012) Mini Rev. Med. Chem., 12, pp. 749-767
  • Salum, M.L., Erra-Balsells, R., (2013) Environ. Control Biol., 52, pp. 1-13
  • Yin, Z.Q., Wong, W.S., Ye, W.C., Li, N., (2003) Chin. Sci. Bull., 48, pp. 555-558
  • Wong, W.S., Guo, D., Wang, X.L., Yin, Z.Q., Xia, B., Li, N., (2005) Plant Physiol. Biochem., 43, pp. 929-937
  • Yang, X.X., Choi, H.W., Yang, S.F., Li, N., (1999) Aust. J. Plant Physiol., 26, pp. 325-335
  • Guo, D., Wong, W.S., Xu, W.Z., Sun, F.F., Qing, D.J., Li, N., (2011) Plant Mol. Biol., 75, pp. 481-495
  • Salum, M.L., Robles, C.J., Erra-Balsells, R., (2010) Org. Lett., 12, pp. 4808-4811
  • Salum, M.L., Erra-Balsells, R., (2009) Argentine Patent, , CONICET #20090105020
  • Salum, M.L., Arroyo Mañez, P., Luque, F.J., Erra-Balsells, R., (2015) J. Photohem. Photobiol. B, 148, pp. 128-135
  • Cooks, R.G., Kruger, T.L., (1977) J. Am. Chem. Soc., 99, pp. 1279-1281
  • Dávalos, J.Z., Roux, M.V., (2000) Meas. Sci. Technol., 11, pp. 1421-1425
  • Sabbah, R., Perez, J.A.G., (1997) Thermochim. Acta, 297, pp. 17-32
  • Hubbard, W.N., Scott, D.W., Waddington, G., (1956) Experimental Thermochemistry, , F.D. Rossini, Interscience New York (chapter 5)
  • Good, W.D., Smith, N.K., (1969) J. Chem. Eng. Data, 14, pp. 102-106
  • Santos, L.M.N.B.F., Lima, L.M.S.S., Lima, C.F.R.A.C., Magalhães, F.D., Torres, M.C., Schröder, B., Ribeiro Da Silva, M.A.V., (2011) J. Chem. Thermodyn., 43, pp. 834-843
  • Cheng, X., Wu, Z., Fenselau, C., (1993) J. Am. Chem. Soc., 115, pp. 4844-4848
  • Armentrout, P.B., (2000) J. Am. Soc. Mass Spectrom., 11 (11), pp. 371-379
  • Bouchoux, G., (2007) Mass Spectrom. Rev., 26, pp. 775-835
  • Guerrero, A., Baer, T., Chana, A., González, J., Dávalos, J.Z., (2013) J. Am. Chem. Soc., 135, pp. 9681-9690
  • Ervin, K.M., (2000) Int. J. Mass Spectrom., 271, pp. 195-196
  • Ren, J., Tan, J.P., Harper, R.T., (2009) J. Phys. Chem. A, 113, pp. 10903-10912
  • Lee, C., Yang, W., Parr, R.G., (1988) Phys. Rev. B, 37, pp. 785-789
  • Curtiss, L.A., Raghavachari, K., Redfern, P.C., Rassolov, V., Pople, J.A., (1998) J. Chem. Phys., 109, pp. 7764-7776
  • Curtiss, L.A., Redfern, P.C., Raghavachari, K., (2007) J. Chem. Phys., 126, p. 084108
  • Nicolaides, A., Rauk, A., Glukhovtsev, M.N., Radom, L., (1996) J. Phys. Chem., 100, pp. 17460-17464
  • Codata, (1975) J. Chem. Thermodyn., 8, pp. 603-605
  • Monte, M.J.S., Hillesheim, D.M., (1999) J. Chem. Thermodyn., 31, pp. 1443-1456
  • Chase, Jr.M.W., Fourth Ed. J. Phys. Chem. Ref, , NIST-JANAF Thermochemical Tables Data 1998, Monograph 9
  • Hanai, K., Kuwae, A., Takai, T., Senda, H., Kunimoto, K.-K., (2001) Spectrochim. Acta A, 57, pp. 513-519
  • Lee, H.-H., Senda, H., Kuwae, A., Hanai, K., (1994) Bull. Chem. Soc. Jpn., 67, pp. 1475-1478
  • Lee, H.-H., Senda, H., Oyama, K., Kuwae, A., Hanai, K., (1994) Bull. Chem. Soc. Jpn., 67, pp. 2574-2576
  • Hehre, W.J., Radom, L., Schleyer V. P, R., Pople, J.A., (1986) Ab Initio Molecular Orbital Theory, , John Wiley & Sons New York
  • Pedley, J.B., (1994) Thermochemical Data and Structures of Organic Compounds, , Thermodynamics Research Center College Station, TX
  • Dávalos, J.Z., Herrero, R., Chana, A., Guerrero, A., Jiménez, P., Santiuste, J.M., (2012) J. Phys. Chem. A, 116, pp. 2261-2267
  • Frederick, J., Dippy, J., Lewis, R.H., (1936) J. Chem. Soc., pp. 644-649
  • Dávalos, J.Z., Guerrero, A., Herrero, R., Jimenez, P., Chana, A., Abboud, J.L.M., Lima, C.F.R.A.C., Lago, A.F., (2010) J. Org. Chem., 75, pp. 2564-2571
  • McMahon, T.B., Kebarle, P., (1997) J. Am. Chem. Soc., 99, pp. 2222-2230

Citas:

---------- APA ----------
Dávalos, J.Z., Lima, C.F.R.A.C., Silva, A.M.S., Santos, L.M.N.B.F., Erra-Balsells, R. & Salum, M.L. (2016) . Energetics of neutral and deprotonated (Z)-cinnamic acid. Journal of Chemical Thermodynamics, 95, 195-201.
http://dx.doi.org/10.1016/j.jct.2015.12.014
---------- CHICAGO ----------
Dávalos, J.Z., Lima, C.F.R.A.C., Silva, A.M.S., Santos, L.M.N.B.F., Erra-Balsells, R., Salum, M.L. "Energetics of neutral and deprotonated (Z)-cinnamic acid" . Journal of Chemical Thermodynamics 95 (2016) : 195-201.
http://dx.doi.org/10.1016/j.jct.2015.12.014
---------- MLA ----------
Dávalos, J.Z., Lima, C.F.R.A.C., Silva, A.M.S., Santos, L.M.N.B.F., Erra-Balsells, R., Salum, M.L. "Energetics of neutral and deprotonated (Z)-cinnamic acid" . Journal of Chemical Thermodynamics, vol. 95, 2016, pp. 195-201.
http://dx.doi.org/10.1016/j.jct.2015.12.014
---------- VANCOUVER ----------
Dávalos, J.Z., Lima, C.F.R.A.C., Silva, A.M.S., Santos, L.M.N.B.F., Erra-Balsells, R., Salum, M.L. Energetics of neutral and deprotonated (Z)-cinnamic acid. J Chem Thermodyn. 2016;95:195-201.
http://dx.doi.org/10.1016/j.jct.2015.12.014