Hydration of thiourea and mono-, di-, and tetra- N -alkylthioureas at infinite dilution: A thermodynamic study at a temperature of 298.15 K

Journal of Chemical and Engineering Data

Volumn 56, Issue 12, 2011, Pages 4778-4785

  Badea, Elena ^a   Della Gatta, Giuseppe ^a   Jóźwiak, Małgorzata ^b   Giancola, Concetta ^c  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF LODZ   (Poland)

^c UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ENTHALPY OF SOLVATION; HOMOLOGOUS SERIES; HYDRATION BEHAVIORS; INFINITE DILUTION; ISOTHERMAL CALORIMETRY; LITERATURE DATA; METHYLENE GROUPS; MOLAR ENTHALPY; MOLAR HEAT CAPACITIES; SOLUTION PROCESS; THERMODYNAMIC STUDIES;

ENTHALPY; FUNCTIONAL GROUPS; HYDRATION; METABOLISM; SOLS; SOLVATION; SPECIFIC HEAT OF SOLIDS; UREA;

THIOUREAS;

EID: 83455235599     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je2007742     Document Type: Article

References (51)

1. Frank, H. S.; Evans, M. W. Free volume and entropy in condensed systems. III. Entropy in binary liquid mixtures; partial molal entropy in dilute solution; structure and thermodynamics in aqueous electrolytes J. Chem. Phys. 1945, 13, 507-532
2. Kautzmann, W. Some factors in the interpretation of protein denaturation Adv. Protein Chem. 1959, 14, 1-63
3. Konicek, J.; Wadsö, I. Thermochemical properties of some carboxylic acids, amines and N -substituted amides in aqueous solution Acta Chem. Scand. 1971, 25, 1541-1551
4. Lilley, T. M. Thermodynamics of peptides and model systems. In Biochemistry Thermodynamics; Jones, M., Ed.; Elsevier: Amsterdam, 1988; pp 1-48.
5. Barone, G.; Giancola, C. Peptide-peptide interactions in water and concentrated urea solutions Pure Appl. Chem. 1990, 62, 57-68
6. Barone, G.; Della Gatta, G.; Del Vecchio, P.; Giancola, C.; Graziano, G. Hydration enthalpy of model peptides: N -acetyl amino acid amides Biophys. Chem. 1994, 51, 193-202
7. Della Gatta, G.; Usacheva, T.; Badea, E.; Pałecz, B.; Ichim, D. Thermodynamics of solvation of some small peptides in water at T = 298.15 K J. Chem. Thermodyn. 2006, 38, 1054-1061
8. Soper, A. K.; Castner, E. W.; Luzar, A. Impact of urea on water structure: a clue to its properties as a denaturant? Biophys. Chem. 2003, 105, 649-666
9. Mountain, R. D.; Thirumalai, D. Importance of excluded volume on the solvation of urea in water J. Phys. Chem. B 2004, 108, 6826-6831
10. Hayashi, Y.; Katsumoto, Y.; Omori, S.; Kishii, N.; Yasuda, A. Liquid structure of the urea-water system studied by dielectric spectroscopy J. Phys. Chem. B 2007, 111, 1076-1080
11. Idrissi, A.; Gerard, M.; Damay, P.; Kiselev, M.; Puhovsky, Y.; Cinar, E.; Lagant, P.; Vergoten, G. The effect of urea on the structure of water: a molecular dynamics simulation J. Phys. Chem. B 2010, 114, 4731-4738
12. Ren, J. S.; Diprose, J.; Warren, J.; Esnouf, R. M.; Bird, L. E.; Ikemizu, S.; Slater, M.; Milton, J.; Balzarini, J.; Stuart, D. I.; Stammers, D. K. Phenylethylthiazolylthiourea (PETT) non-nucleoside inhibitors of HIV-1 and HIV-2 reverse transcriptases. Structural and biochemical analyses J. Biol. Chem. 2000, 275, 5633-5639
13. 2+ recognition by 1,3-diphenyl-thiourea J. Phys. Chem. A 2003, 107, 9000-9007
14. Thiagarajan, V.; Ramamurthy, P.; Thirumalai, D.; Ramakrishnan, V. T. A novel colorimetric and fluorescent chemosensor for anions involving PET and ICT pathways Org. Lett. 2005, 7, 657-660
15. Gomez, D. E.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. Urea vs thiourea in anion recognition Org. Biomol. Chem. 2005, 3, 1495-1500
16. Barone, G.; Cacace, P.; Castronuovo, G.; Elia, V. Interactions in aqueous solutions of urea-like compounds. Heats of mixing of urea, monomethylurea and thiourea at 298.15 K J. Chem. Soc., Faraday Trans. 1981, 77, 1569-1577
17. Barone, G.; Cacace, P.; Della Gatta, G.; De Sena, R.; Giancola, C. Interactions in aqueous solutions of alkylthioureas. Excess enthalpies at 298.15 K Thermochim. Acta 1992, 199, 229-233
18. Della Gatta, G.; Badea, E.; Jóźwiak, M.; Del Vecchio, P. Thermodynamics of solvation of urea and some monosubstituted N -alkylureas in water at 298.15 K J. Chem. Eng. Data 2007, 52, 419-425
19. Della Gatta, G.; Badea, E.; Jóźwiak, M.; Barone, G. Hydrophobic-hydrophilic solvation of variously substituted N -alkylureas in aqueous solution: a calorimetric study at a temperature of 298.15 K J. Chem. Eng. Data 2009, 54, 2739-2744
20. Schmidtchen, F. P.; Berger, M. Artificial Organic Host Molecules for Anions Chem. Rev. 1997, 97, 1609-1646
21. Miyabe, H.; Takemoto, Y. Discovery and application of asymmetric reaction by multi-functional thioureas Bull. Chem. Soc. Jpn. 2008, 81 (7) 785-795
22. Custelcean, R. Crystal engineering with urea and thiourea hydrogen-bonding groups Chem. Commun. 2008, 295-307
23. Della Gatta, G.; Jóźwiak, M.; Brunetti, B.; Abate, L. Enthalpies and entropies of fusion and of sublimation at the temperature 298.15 K of thiourea and seven N -alkylthioureas J. Chem. Thermodyn. 2000, 32, 979-997
24. Abate, L.; Jóźwiak, M.; Della Gatta, G. Heat capacities of thiourea and some N -alkylthioureas Thermochim. Acta 1997, 303, 63-68
25. Plato, C. Differential scanning calorimetry as a general method for determining purity and heat of fusion of high-purity organic chemicals Anal. Chem. 1972, 44, 1531-1534
26. Della Gatta, G.; Stradella, L.; Venturello, P. Enthalpies of solvation in cyclohexane and in water for homologous aliphatic ketones and esters J. Solution Chem. 1981, 3, 209-220
27. Marsh, K. N.; Stokes, R. H. Enthalpies of mixing of n -hexane + cyclohexane at 25 °C J. Chem. Thermodyn. 1969, 1, 223-225
28. Wadsö, I.; Goldberg, R. N. Standards in isothermal microcalorimetry (IUPAC technical report) Pure Appl. Chem. 2001, 73, 1625-1639
29. Taniewska-Osińska, S.; Pałecz, B. Enthalpies of solution of thiourea in water from 293.15 to 333.15 K J. Chem. Thermodyn. 1980, 12, 775-778
30. Kumler, W. D.; Fohlen, G. M. The dipole moment and structure of urea and thiourea J. Am. Chem. Soc. 1942, 64, 1944-1948
31. Orita, Y.; Ando, A.; Abe, H. Quantum mechanical studies of environmental effects on biomolecules. IX. Structure and hydration of thiourea Theor. Chim. Acta (Berlin) 1979, 54, 73-82
32. Weiqun, Z.; Wen, Y.; Lihua, Q. Structure and stability of thiourea with water, DFT and MP2 calculations J. Mol. Struct.: THEOCHEM 2005, 730, 133-141
33. Toth, K.; Bopp, P.; Jancsó, G. Ab initio studies on the interactions of water with tetramethylurea and tetramethylthiourea J. Mol. Struct. 1996, 381, 181-187
34. Bastos, M.; Kimura, T.; Wadsö, I. Some thermodynamic properties of dialkylsulphides and dialkyldisulphides in aqueous solution J. Chem. Thermodyn. 1991, 23 (11) 1069-1074
35. Nilsson, S.-O.; Wadsö, I. Thermodynamic properties of some mono-, di-, and tri-esters enthalpies of solution in water at 288.15 to 318.15 K and enthalpies of vaporization and heat capacities at 298.15 K J. Chem. Thermodyn. 1986, 18, 673-681
36. Kusano, K.; Suurkuusk, J.; Wadsö, I. Thermochemistry of solutions of biochemical model compounds. 2. alkoxyethanols and 1,2-dialkoxyethanes in water J. Chem. Thermodyn. 1973, 5, 757-767
37. Makhatdze, G.; Privalov, P. Contribution of hydration to protein folding thermodynamics: the enthalpy of hydration J. Mol. Biol. 1993, 232, 639-659
38. Cabani, S.; Gianni, P.; Mollica, V.; Lepori, L. Group contributions to the thermodynamic properties of non-ionic organic solutes in dilute aqueous solution J. Solution Chem. 1981, 10, 563-595
39. Ben-Naim, A.; Marcus, Y. Solvation thermodynamics of nonionic solutes J. Chem. Phys. 1984, 81, 2016-2027
40. Marcus, Y. A simple empirical model describing the thermodynamics of hydration of ions of widely varying charges, sizes and shapes Biophys. Chem. 1994, 51, 111-128
41. Privalov, P. L.; Gill, S. J. Stability of protein structure and hydrophobic interaction Adv. Protein Chem. 1988, 39, 191-234
42. Murphy, K. P.; Privalov, P. L.; Gill, S. J. Common features of protein unfolding and dissolution of hydrophobic compounds Science 1990, 247, 559-561
43. Baldwin, R. Temperature dependence of the hydrophobic interaction in protein folding Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 8069-8072
44. Subramanian, S.; Sarma, T. S.; Balasubramanian, D.; Ahluwalia, J. C. Effects of the urea-guanidinium class of protein denaturants on water structure: heats of solution and proton chemical shift studies J. Phys. Chem. 1971, 75, 815-820
45. Nichols, N.; Sköld, R.; Spink, C.; Suurskuusk, J.; Wadsö, I. Additivity relations for the heat capacities of nonelectrolytes in aqueous solution J. Chem. Thermodyn. 1976, 8, 1081-1093
46. Makhatadze, G. I.; Lopez, M. M.; Privalov, P. L. Heat capacities of protein functional groups Biophys. Chem. 1997, 64, 93-101
47. Madan, B.; Sharp, K. Molecular origin of hydration heat capacity changes of hydrophobic solutes perturbation of water structure around alkanes J. Phys. Chem. B 1997, 101, 11237-11242
48. Roux, G.; Perron, G.; Desnoyers, J. E. The heat capacities and volumes of some low molecular weight amides, ketones, esters and ethers in water over the whole solubility range Can. J. Chem. 1978, 56, 2808-2814
49. Olofsson, G.; Oshodj, A. A.; Qvarnström, E.; Wadsö, I. J. Calorimetric measurements on slightly soluble gases in water enthalpies of solution of helium, neon, argon, krypton, xenon, methane, ethane, propane, n-butane, and oxygen at 288.15, 298.15, and 308.15 K J. Chem. Thermodyn. 1984, 16, 1041-1052
50. Gallagher, K. R.; Sharp, K. A. A new angle on heat capacity changes in hydrophobic solvation J. Am. Chem. Soc. 2003, 125, 9853-9860
51. Della Gatta, G.; Barone, G.; Abate, L. Thermodynamics of hydration of polyhydric alcohols. In Water-Biomolecules Interactions; Palma, M. U.; Palma-Vittorelli, M. B.; Parak, F., Eds.; SIF: Bologna, 1993; pp 269-272.