Thermophysical study of several α- And β-amino acid derivatives by differential scanning calorimetry (DSC)

Journal of Chemical and Engineering Data

Volumn 56, Issue 10, 2011, Pages 3807-3812

  Roux, María Victoria ^a   Notario, Rafael ^a   Segura, Marta ^b   Guzmán Mejía, Ramón ^c   Juaristi, Eusebio ^c   Chickos, James S ^d  

^a INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^b PerkinElmer España SL ^*  (Spain)

^c DEPARTAMENTO DE FÍSICA   (Mexico)

^d UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVES; HEAT CAPACITIES; SARCOSINE; TEMPERATURE INTERVALS; THERMOPHYSICAL;

DIFFERENTIAL SCANNING CALORIMETRY;

AMINO ACIDS;

EID: 80054679511     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je200292z     Document Type: Article

References (54)

1. Nelson, G.; Chandrashekar, J.; Hoon, M.; Feng, L. X.; Zhao, G.; Ryba, N. J. P.; Zuker, C. S. An Amino-Acid Taste Receptor Nature (London) 2002, 416, 199-202 (Pubitemid 34246480)
2. Brack, A., Ed. The Molecular Origins of Life; Cambridge University Press: Cambridge, U.K., 1998.
3. Allen, F. H. The Cambridge Structural Database: A Quarter of a Million Crystal Structures and Rising Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 2002, 58, 380-388 (Pubitemid 135702674)
4. Levy, H. A.; Corey, R. B. The Crystal Structure of dl -Alanine J. Am. Chem. Soc. 1941, 63, 2095-2108
5. Donohue, J. The Crystal Structure of dl -Alanine. II. Revision of Parameters by Three-Dimensional Fourier Analysis J. Am. Chem. Soc. 1950, 72, 949-953
6. Chickos, J. S. A Protocol for Correcting Experimental Fusion Enthalpies to 298.15 K and Its Application in Indirect Measurements of Sublimation Enthalpy at 298.15 K Thermochim. Acta 1998, 313, 19-26 (Pubitemid 128349460)
7. Chickos, J. S.; Hesse, D. G.; Hosseini, S.; Nichols, G.; Webb, P. Sublimation Enthalpies at 298.15 K Using Correlation Gas Chromatography and Differential Scanning Calorimetry Measurements Thermochim. Acta 1998, 313, 101-111
8. Chickos, J. S.; Hosseini, S.; Hesse, D. G.; Liebman, J. F. Heat Capacity Corrections to a Standard State: A Comparison of New and Some Literature Methods for Organic Liquids and Solids Struct. Chem. 1993, 4, 271-278
9. Zábranský, M.; Kolská, Z.; Rüžič ka, V., Jr.; Domalski, E. S. Heat Capacity of Liquids: Critical Review and Recommended Values. Supplement II J. Phys. Chem. Ref. Data 2010, 39, 013103
10. Zábranský, M.; Rüžička, V., Jr.; Domalski, E. S. Heat Capacity of Liquids: Critical Review and Recommended Values. Supplement I J. Phys. Chem. Ref. Data 2001, 30, 1199-1689
11. Zábranský, M.; Rüžička, V., Jr.; Majer, V.; Domalski, E. S. Heat Capacity of Liquids: Volume 1-Critical Review and Recommended Values. J. Phys. Chem. Ref. Data 1996, Monograph 6.
12. Palczewska-Tulinska, M.; Wyrzykowska-Stankiewicz, D.; Szafranski, A. M.; Cholinski, J. Solid and Liquid Heat Capacity Data Collection, Part 1: C1-C6; Dechema, Chem. Technik und Biotechnologie e.V.: Frankfurt am Main, 1997.
13. Palczewska-Tulinska, M.; Wyrzykowska-Stankiewicz, D.; Szafranski, A. M.; Cholinski, J. Solid and Liquid Heat Capacity Data Collection, Part 2: C6-C33; Dechema, Chem. Technik und Biotechnologie e.V.: Frankfurt am Main, 1997.
14. Zábranský, M.; Rüžička, V. Heat Capacity of Liquids: A Survey and Data Needs Fluid Phase Equilib. 2002, 194, 817-824 (Pubitemid 34242605)
15. Becker, L.; Gmehling, J. Measurement of Heat Capacities for 12 Organic Substances by Tian-Calvet Calorimetry J. Chem. Eng. Data 2001, 46, 1638-1642 (Pubitemid 33073944)
16. Chickos, J. S.; Hesse, D. G.; Liebman, J. F. A Group Additivity Approach for the Estimation of Heat Capacities of Organic Liquids and Solids at 298 K Struct. Chem. 1993, 4, 261-269
17. Goodman, B. T.; Wilding, W. V.; Oscarson, J. L.; Rowley, R. L. Use of the DIPPR Database for Development of Quantitative Structure-Property Relationship Correlations: Heat Capacity of Solid Organic Compounds J. Chem. Eng. Data 2004, 49, 24-31
18. Rüžička, V., Jr.; Domalski, E. S. Estimation of the Heat-Capacities of Organic Liquids as a Function of Temperature Using Group Additivity. 1. Hydrocarbon Compounds J. Phys. Chem. Ref. Data 1993, 22, 597-618
19. Rüžička, V., Jr.; Domalski, E. S. Estimation of the Heat-Capacities of Organic Liquids as a Function of Temperature Using Group Additivity. 2. Compounds of Carbon, Hydrogen, Halogens, Nitrogen, Oxygen, and Sulfur J. Phys. Chem. Ref. Data 1993, 22, 619-657
20. Zabransky, M.; Rüžička, V. Estimation of the Heat Capacity of Organic Liquids as a Function of Temperature Using Group Additivity: An Amendment J. Phys. Chem. Ref. Data 2004, 33, 1071-1081 (Pubitemid 41025525)
21. Góralski, P.; Tkaczyk, M. Heat Capacities of Some Liquid α,γ-Alkanediamines in the Temperature Range Between (293.15 and 353.15) K J. Chem. Eng. Data 2010, 55, 953-955
22. Acree, W., Jr.; Chickos, J. S. Phase Change Enthalpies and Entropies of Liquid Crystals J. Phys. Chem. Ref. Data 2006, 35, 1051-1330 (Pubitemid 44376084)
23. Jiménez, P.; Roux, M. V.; Dávalos, J. Z.; Temprado, M. Heat Capacities and Enthalpies of Transitions of Three Nitrobenzonitriles Thermochim. Acta 2002, 394, 25-29
24. Roux, M. V.; Temprado, M.; Jiménez, P.; Dávalos, J. Z.; Foces-Foces, C.; García, M. V.; Redondo, M. I. Thermophysical, Crystalline and Infrared Study of 2- and 3-Thiophenecarboxylic acids Thermochim. Acta 2003, 404, 235-244
25. p Group Values for Organosulfur Compounds and Their Oxides Thermochim. Acta 2003, 406, 9-16
26. Roux, M. V.; Temprado, M.; Jiménez, P.; Foces-Foces, C.; García, M. V.; Redondo, M. I. 2- and 3-Furancarboxylic Acids: A Comparative Study Using Calorimetry, IR Spectroscopy and X-ray Crystallography Thermochim. Acta 2004, 420, 59-66
27. Temprado, M.; Roux, M. V.; Jiménez, P.; Guzmán- Mejía, R.; Juaristi, E. Thermophysical Properties of Sulfur Heterocycles: Thiane and Thiophene Derivatives Thermochim. Acta 2006, 441, 20-26 (Pubitemid 43108980)
28. Temprado, M.; Roux, M. V.; Parameswar, A. R.; Demchenko, A. V.; Chickos, J. S.; Liebman, J. F. Thermophysical Properties in Medium Temperature Range of Several Thio and Dithiocarbamates J. Therm. Anal. Calorim. 2008, 91, 471-475 (Pubitemid 351231709)
29. Temprado, M.; Roux, M. V.; Chickos, J. S. Some Thermophysical Properties of Several Solid Aldehydes J. Therm. Anal. Calorim. 2008, 94, 257-262
30. Temprado, M.; Roux, M. V.; Ros, F.; Notario, R.; Segura, M.; Chickos, J. S. Thermophysical Study of Several Barbituric Acid Derivatives by Differential Scanning Calorimetry (DSC) J. Chem. Eng. Data 2011, 56, 263-268
31. Foces-Foces, C.; Roux, M. V.; Notario, R.; Segura, M. Thermal Behavior and Polymorphism in Medium-High Temperature Range of the Sulfur Containing Amino Acids L-Cysteine and L-Cystine. J. Therm. Anal. Calorim. 2011, DOI 10.1007/s10973-011-1302-6.
32. Ribeiro da Silva, M. A. V.; Ribeiro da Silva, M. D. M. C.; Santos, A. F. L. O. M.; Roux, M. V.; Foces-Foces, C.; Notario, R.; Guzmán-Mejía, R.; Juaristi, E. Experimental and Computational Thermochemical Study of α-Alanine (dl) and β-Alanine J. Phys. Chem. B 2010, 114, 16471-16480
33. Notario, R.; Roux, M. V.; Foces-Foces, C.; Ribeiro da Silva, M. A. V.; Ribeiro da Silva, M. D. M. C.; Santos, A. F. L. O. M.; Guzmán- Mejía, R.; Juaristi, E. Experimental and Computational Thermochemical Study of N -Benzyl-alanines J. Phys. Chem. B 2011, 115, 9401-9409
34. Huffman, H. M.; Ellis, E. L. Thermal data. VIII. The Heat Capacities, Entropies and Free Energies of Some Amino Acids J. Am. Chem. Soc. 1937, 59, 2150-2152
35. Spink, C. H.; Wadsö, I. Thermochemistry of Solutions of Biochemical Model Compounds. 4. The Partial Molar Heat Capacities of Some Amino Acids in Aqueous Solution J. Chem. Thermodyn. 1975, 7, 561-572
36. Kulikov, O. V.; Kozlov, V. A.; Malenkina, L. I.; Badelin, V. G. Heat Capacities of Amino Acids and Peptides and Excess Characteristics of Their Aqueous Solutions. Sbornik Nauch. Trud., Termodin. Rast. Neelect., Ivanovo, Inst. Nevod. Rast. Akad. Nauk, SSSR 1989, 36-42. (Taken from NIST Webbook: http://webbook.nist.gov/chemistry).
37. Badelin, V. G.; Kulikov, O. V.; Vatagin, V. S.; Udzig, E.; Zielenkiewicz, A.; Zielenkiewicz, W.; Krestov, G. A. Physico-Chemical Properties of Peptides and Their Solutions Thermochim. Acta 1990, 169, 81-93
38. Skoulika, S.; Sabbah, R. Thermodynamique de Composes Azotes X. Etude Thermochimique de Quelques Acides γ-Amines Thermochim. Acta 1983, 61, 203-214
39. Paukov, I. E.; Kovalevskaya, Y. A.; Boldyreva, E. V.; Drebushchak, V. A. Heat Capacity of β-Alanine in a Temperature Range Between 6 and 300 K J. Therm. Anal. Calorim. 2009, 98, 873-876
40. Sabbah, R.; Laffitte, M. The Enthalpy of Formation of Sarcosine in the Solid State J. Chem. Thermodyn. 1977, 9, 1107-1108
41. Harada, K.; Okawara, T. Sterically Controlled Syntheses of Optically Active Organic Compounds. XVII. Asymmetric Syntheses of Amino Acids by Addition of Benzoyl Cyanide to the Azomethine Compounds Bull. Chem. Soc. Jpn. 1973, 46, 191-193
42. Zilkha, A.; Rachman, E. S.; Rivlin, J. Syntheses of β-Amino Acids and Their N-Alkyl Derivatives J. Org. Chem. 1961, 26, 376-380
43. Marti, E. E. Purity Determination by Differential Scanning Calorimetry Thermochim. Acta 1973, 5, 173-220
44. Della Gatta, G.; Richardson, M. J.; Sarge, S. M.; Stølen, S. Standards, Calibration, and Guidelines in Microcalorimetry. Part 2. Calibration Standards for Differential Scanning Calorimetry Pure Appl. Chem. 2006, 78, 1455-1476
45. Gmelin, E.; Sarge, S. M. Temperature, Heat and Heat Flow Rate Calibration of Differential Scanning Calorimeters Thermochim. Acta 2000, 347, 9-13
46. GEFTA (Gesellschaft für Thermische Analyse, Germany). Gmelin, E.; Sarge, S. M. Calibration of Differential Scanning Calorimeters Pure Appl. Chem. 1995, 67, 1789-1800
47. Sabbah, R.; Xu-wu, A.; Chickos, J. S.; Planas Leitão, M. L.; Roux, M. V.; Torres, L. A. Reference Materials for Calorimetry and Differential Thermal Analysis Thermochim. Acta 1999, 331, 93-204 (Pubitemid 129506321)
48. Mraw, S. C.; Naas, D. F. The Measurement of Accurate Heat Capacities by Differential Scanning Calorimetry. Comparison of DSC Results on Pyrite (100 to 800 K) with Literature Values from Precision Adiabatic Calorimetry J. Chem. Thermodyn. 1979, 11, 567-584
49. O'Neill, M. J. Measurement of Specific Heat Functions by Differential Scanning Calorimetry Anal. Chem. 1966, 38, 1331-1336
50. Callanan, J. E.; Sullivan, S. A. Development of Standard Operating Procedures for Differential Scanning Calorimeters Rev. Sci. Instrum. 1986, 57, 2584-2592
51. Pak, J.; Qiu, W.; Pyda, M.; Nowak-Pyda, E.; Wunderlich, B. Can One Measure Precise Heat Capacities with DSC or TMDSC?: A Study of the Baseline and Heat-Flow Rate Correction J. Therm. Anal. Calorim. 2005, 82, 565-574 (Pubitemid 43077009)
52. Rudtsch, S. Uncertainty of Heat Capacity Measurements with Differential Scanning Calorimeters Thermochim. Acta 2002, 382, 17-25
53. Wieser, M. E. Atomic Weights of the Elements 2009 (IUPAC technical report) Pure Appl. Chem. 2011, 382, 17-25
54. Chickos, J. S.; Acree, W. E., Jr. Total Phase Change Entropies and Enthalpies: An Update on Fusion Enthalpies and Their Estimation Thermochim. Acta 2009, 495, 5-13