Thermodynamic properties of inclusion complexes of α-cyclodextrin + aliphatic nitriles (H(CH 2) nCN: N 5 1-8) in aqueous solution

Journal of Thermal Analysis and Calorimetry

Volumn 108, Issue 2, 2012, Pages 695-704

  Kimura, Takayoshi ^a   Yukiyama, Takashi ^a   Fujisawa, Masao ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

Aliphatic nitriles cyclodextrin; Aqueous solutions; DFT; Molecular inclusion; Thermodynamic properties

Indexed keywords

ALIPHATIC NITRILES; DFT; DFT CALCULATION; DILUTE AQUEOUS SOLUTION; DRIVING FORCES; GASPHASE; GUEST MOLECULES; INCLUSION COMPLEX; INCLUSION ENERGY; INCLUSION REACTION; INTERACTION ENERGIES; MICROCALORIMETER; NON-POLAR; SOLVENT EFFECTS;

CYANIDES; DENSITY FUNCTIONAL THEORY; THERMODYNAMIC PROPERTIES;

SOLUTIONS;

EID: 84860766471     PISSN: 13886150     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10973-011-2144-y     Document Type: Conference Paper

References (39)

1. Takagi S, Kimura T, Maeda M. Some problems in solution calorimetry, experimental experiences by authors, and enthalpyentropy compensation in cyclodextrin + alcohol inclusion-complex formation in aqueous solutions. Thermochim Acta. 1985;88: 247-54.
2. Takagi S, Fujisawa M, Kimura T. Enthalpy and entropy changes on molecular inclusion of 1,3-butanediol into α-and β-cyclodextrin cavities in aqueous solutions. Thermochim Acta. 1991;183:289-97.
3. Maeda M, Takagi S. Calorimetric studies on molecular inclusion. III. Gibbs energies and entropies of inclusion of 1-propanol and 1-pentanol into cyclohexaamylose and cycloheptaamylose in aqueous solutions at 298.15 K. Netsu Sokutei. 1983;10:103-7.
4. Takagi, S, Maeda M. Enthalpy of inclusion of methanol, 1-propanol, 1-pentanol into α-cyclodextrin cavities in aqueous solutions at 298.15 K. Nippon Kagakukai Shi. 1983: 1983; 188-194.
5. Takagi S, Maeda M. Calorimetric determination of enthalpies, Gibbs energies and entropies of inclusion of some alcohols into aand β-cyclodextrins in aqueous solutions. J Incl Phenom. 1984;2:775-80.
6. Fujisawa M, Kimura T, Takagi S. Enthalpy and entropy changes on molecular inclusion of 1-butanol into α-and β-cyclodextrin cavities in aqueous solutions. Netsusokutei. 1991;18:71-6.
7. Takagi S, Fujisawa M, Kimura T. Moleclular recognition. In: Salamone JC, editor. Polymeric materials encyclopedia cyclodextrins. Boca Raton: CRC press Inc.; 1996. p. 1709-15.
8. Fujisawa M, Kimura T, Takagi S. The enthalpic stabilisation on molecular inclusion of butanediol isomers into cyclodextrin cavities. Fluid Phase Equilib. 1997;163:197-205. (Pubitemid 127434108)
9. Fujisawa M, Kimura T, Takagi S. Thermodynamic functions of molecular inclusion of some isomers of butanediol in gas phase into α-and β-cyclodextrin cavities in aqueous solutions at 298.15 K. J Thermal Anal Calorim. 2001;64:149-55. (Pubitemid 32512107)
10. Fujisawa M, Kimura T. Enthalpy and entropy changes on molecular inclusion of 1-heptanol into α-and β-cyclodextrin cavities in aqueous solutions. Thermochim Acta. 2004;416:51-4.
11. Kimura T, Fujisawa M, Nakano Y, Kamiyama T, Otsu T, Maeda M, Takagi S. Calorimetric study on inclusion of some alcohols into acyclodextrin cavities; molecular mechanical calculation of hydration Gibbs energies. J Thermal Anal Calorim. 2007;90:581-5. (Pubitemid 350230166)
12. Kimura T, Fujie S, Yukiyama T, Kamiyama T, Fujisawa M, Aki H. Enthalpy and entropy changes on molecular inclusion of pentane derivertives into α-cyclodextrin cavities in aqueous solutions. J. Incl. Phenom. Mcrocycl. Chem. 2011;70:269-78.
13. Bastos M, Briggner L-E, Shehatta I, Wadsö I. The binding of alkane-α, ω-diols to α-cyclodextrin. A microcalorimetric study. J Chem Thermodyn. 1990;22:1181-90.
14. Bastos M, Afonso M, Cacote MHM, Ramos MJ. Interactions in the model system α-cyclodextrin-glycerol Experimental and theoretical study. J Chem Soc Faraday Trans. 1997;93:2061-7.
15. Bastos M, Milheiras S, Bai G. Enthalpy of solution of α-cyclodextrin in water and in formamide at 298.15 K. Thermochim Acta. 2004;420:111-7.
16. Moreira R, Bastos M. The influence of glycerol on ligand binding equilibria between monoalcohols and α-cyclodextrin. J Chem Thermodyn. 2000;32:1539-50. (Pubitemid 32043422)
17. Rekharsky M, Inoue Y. Complexation thermodynamics of cyclodextrins. Chem Rev. 1998;98:1875-918.
18. Ross PD, Rekharsky MV. Thermodynamics of hydrogen bond and hydrophobic interactions in cyclodextrin complexes. Biophys J. 1996;71:2144-54. (Pubitemid 26325994)
19. Rekharsky MV, Schwarz FP, Tewari YB, Goldberg RN. A thermodynamic study of the reactions of cyclodextrins with primary and secondary aliphatic alcohols, with D-and L-phenylalanine, and with L-phenylalanine amide. J Phys Chem. 1994;98: 10282-8.
20. Connors KA. The stability of cyclodextrin complexes in solution. Chem Rev. 1997;97:1325-58.
21. Rekharsky MV, Inoue Y. Microcalorimetry. In: Dodziuk H, editor. Cyclodextrins and their complexes: Chemistry, analytical methods, applications. Weinheim: Wiley-VCH Verlag GmbH & Co.; 2006. p. 199-230.
22. Spencer JN, DeGarmo IJ, Paul IM, He Q, Ke X, Wu Z, Yoder CH, Chen S, Mihalick JE. Inclusion complexes of alcohols with α-cyciodextrin. J Solut Chem. 1995;24:601-9.
23. Barone G, Castronuovo G, Del Vecchio P, Elia V, Muscetta M. Thermodynamics of formation of inclusion compounds in water. α-Cyclodextrin-alcohol adducts at 298.15 K. J Chem Soc Faraday Trans. 1986;82:2089-101.
24. Kimura T, Imamura H, Shimowada A, Takagi S. Elimination processes of guest molecules from the inclusion complexes of deoxycholic acid. J Mass Spectrom Soc Jpn. 2003;51:242-6.
25. Kimura T, Takagi S. Determination of excess volumes of benzene + o-terphenyl at 288.15, 298.02, and 302.78 K. J Chem Thermodyn. 1979;11:119-24.
26. Kimura T, Matsushita T, Ueda K, Tamura K, Takagi S. Deuterium isotope effect on excess enthalpies of methanol or ethanol and their deuterium derivatives. J Thermal Anal Calorim. 2001;64:231-41. (Pubitemid 32512116)
27. Kimura T, Ozaki T, Nakai Y, Takeda K, Takagi S. Excess enthalpies of binary mixtures of propanediamine + propanediol at 298.15 K. J Thermal Anal. 1998;54:285-96. (Pubitemid 128511574)
28. Wadsö I, Goldberg RN. Pure Appl Chem. 2001;73:1625-39.
29. Chacko KK, Saenger W. Topography of cyclodextrin inclusion complexes. 15. Crystal and molecular structure of the cyclohexaamylose-7.57 water complex, form III. Four-and siω-membered circular hydrogen bonds. J Am Chem Soc. 1981;103: 1708-15.
30. Cossin M, Rega N, Scalmani G, Barone V. Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J Comp Chem. 2003;24:669-81.
31. Chalasinski G, Szczeniak MM. On the connection between the supermolecular Møller-Plesset treatment of the interaction energy and the perturbation theory of intermolecular forces. Mol Phys. 1988;63:205-24.
32. Gaussian 09, revision A.02. Gaussian, Inc., Pittsburgh; 2009.
33. Fujisawa M, Maeda M, Takagi S, Kimura T. Enthalpies of dilution of mono-, di-and polyalcohols in dilute aqueous solutions at 298.15 K. J Therm Anal Calorim. 2002;69:841-8. (Pubitemid 35227868)
34. Grimme S. Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J Comp Chem. 2006;27:1787-99. (Pubitemid 44672561)
35. Hamprecht FA, Cohen A, Tozer DJ, Handy NC. Development and assessment of new exchange-correlation functionals. J Chem Phys. 1998;109:6264-71. (Pubitemid 128674334)
36. Morikawa T, Brian T. Newbold, analogous odd-even parities. Math Chem. 2003;12:445-50.
37. Nooner DW, Oró J. Organic complexes in meteorites-I. Aliphatic hydrocarbons. Geochim Cosmochim Acta. 1967;31: 1359-94.
38. Cingolani A, Berchiesi G. Thermodynamic properties of organic complexs. J Thermal Anal Calorim. 1974;6:87-91.
39. Acree WE. Thermodynamic properties of organic compounds: Enthalpy of fusion and melting point temperature compilation. Thermochim Acta. 1991;189:37-56.