New group-contribution approach to thermochemical properties of organic compounds: Hydrocarbons and oxygen-containing compounds

Journal of Physical and Chemical Reference Data

Volumn 42, Issue 3, 2013, Pages

  Verevkin, S P ^a   Emel'yanenko, V N ^a   Diky, V ^b   Muzny, C D ^b   Chirico, R D ^b   Frenkel, M ^b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

Author keywords

1,4 interactions; 1,5 interactions; Enthalpy of formation; Enthalpy of vaporization; Group contribution; Hydrocarbons; Oxygen containing compounds

Indexed keywords

CARBON; ENTHALPY; KETONES; VAPORIZATION;

1,4-INTERACTIONS; 1,5-INTERACTIONS; ENTHALPY OF FORMATION; ENTHALPY OF VAPORIZATION; GROUP CONTRIBUTIONS; OXYGEN-CONTAINING COMPOUNDS;

HYDROCARBONS;

EID: 84884971487     PISSN: 00472689     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.4815957     Document Type: Article

References (72)

1. Majer V. Svoboda V. Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation 1985, and (Blackwell Scientific, Oxford).
2. Pedley J.P. Naylor R.D. Kirby S.P. Thermochemical Data of Organic Compounds 1986, and 2nd ed. (Chapman and Hall, London).
3. Pedley J.P. Thermochemical Data and Structures of Organic Compounds 1994, (TRC, College Station, TX).
4. Benson S.W. Thermochemical Kinetics 1976, (Wiley, New York).
5. Domalski E.S. Hearing E.D. J. Phys. Chem. Ref. Data 1993, 22:805. 10.1063/1.555927, and.
6. Cohen N. J. Phys. Chem. Ref. Data 1996, 25:1411. 10.1063/1.555988.
7. Santos R.C. Leal J.P. J. Phys. Chem. Ref. Data 2012, 41:043101. 10.1063/1.4754596, and.
8. Diky V.V. Frenkel M. Karpushenkava L.S. Thermochim. Acta 2003, 408:115. 10.1016/S0040-6031(03)00318-6, and.
9. Bashir-Hashemi A. Chickos J.S. Hanshaw W. Zhao H. Farivar B.S. Liebman J.F. Thermochim. Acta 2004, 424:91. 10.1016/j.tca.2004.05.022, and.
10. Thermochemistry and Equilibria of Organic Compounds 1993, M. Frenkel, edited by (VCH, New York).
11. Domalski E.S. Hearing E.D. J. Phys. Chem. Ref. Data 1988, 17:1637. 10.1063/1.555814, and.
12. Salmon A. Dalmazzone D. J. Phys. Chem. Ref. Data 2006, 35:1443. 10.1063/1.2203111, and.
13. Salmon A. Dalmazzone D. J. Phys. Chem. Ref. Data 2007, 36:19. 10.1063/1.2435401, and.
14. NIST Chemistry WebBook 2013, P. J. Linstrom, W. G. Mallard, NIST Standard Reference Database No. 69, edited by and (National Institute of Standards and Technology, Gaithersburg, MD), see.
15. Database of Thermochemical Values, Version 7.0 2004, Fraunhofer Institut für Chemische Technologie, Postfach 1240, 76318 Pfinztal, Berghausen, Germany.
16. Steele W.V. Chirico R.D. Knipmeyer S.E. Nguyen A. Smith N.K. J. Chem. Eng. Data 1996, 41:1285. 10.1021/je960117w, and.
17. Verevkin S.P. Beckhaus H.D. Belen'kaja R.S. Rakus K. Rüchardt C. Thermochim. Acta 1996, 279:47. 10.1016/0040-6031(96)90061-1, and.
18. Rakus K. Verevkin S.P. Keller M. Beckhaus H.D. Rüchardt C. Liebigs Ann. 1995, 1995:1483. 10.1002/jlac.1995199508203, and.
19. Verevkin S.P. Struct. Chem. 1998, 9:375. 10.1023/A:1022471228499.
20. Kulikov D. Verevkin S.P. Heintz A. Fluid Phase Equilib. 2001, 192:187. 10.1016/S0378-3812(01)00633-1, and.
21. Nölke M. Verevkin S.P. Beckhaus H.D. Rüchardt C. Liebigs Ann. 1995, 1995:41. 10.1002/jlac.199519950108, and.
22. Verevkin S.P. J. Chem. Eng. Data 2000, 45:953. 10.1021/je990282m.
23. Verevkin S.P. J. Chem. Eng. Data 2002, 47:1071. 10.1021/je020023o.
24. Roganov G.N. Pisarev P.N. Emel'yanenko V.N. Verevkin S.P. J. Chem. Eng. Data 2005, 50:1114. 10.1021/je049561m, and.
25. Frenkel M. Dynamic compilation: A key concept for future thermophysical data evaluation. Report on Forum 2000: Fluid Properties for New Technologies - Connecting Virtual Design with Physical Reality 2001, J. C. Rainwater, D. G. Friend, H. J. M. Hanley, A. H. Harvey, C. D. Holcomb, A. Laesecke, J. W. Magee, C. Muzny, in edited by and (NIST Special Publication 975, Gaithersburg).
26. Frenkel M. Chirico R.D. Diky V.V. Yan X. Dong Q. Muzny C. J. Chem. Inf. Model. 2005, 45:816. 10.1021/ci050067b, and.
27. Chirico R.D. Frenkel M. Diky V.V. Marsh K.N. Wilhoit R.C. J. Chem. Eng. Data 2003, 48:1344. 10.1021/je034088i, and.
28. Frenkel M. J. Chem. Eng. Data 2009, 54:2411. 10.1021/je800877f.
29. Diky V.V. Chirico R.D. Wilhoit R.C. Dong Q. Frenkel M. J. Chem. Inf. Comput. Sci. 2003, 43:15. 10.1021/ci025534t, and.
30. Guide to the Expression of Uncertainty in Measurement 1993, ISO, (International Organization for Standardization, Geneva, Switzerland). This Guide was prepared by ISO Technical Advisory Group 4 (TAG 4), Working Group 3 (WG 3). ISO/TAG 4 has as its sponsors the BIPM (Bureau International des Poids et Mesures), IEC (International Electrotechnical Commission), IFCC (International Federation of Clinical Chemistry and Laboratory Medicine), ISO, IUPAC (International Union of Pure and Applied Chemistry), IUPAP (International Union of Pure and Applied Physics), and OIML (Organisation Internationale de Métrologie Légale). Although the individual members of WG 3 were nominated by the BIPM, IEC, ISO, or OIML, the Guide is published by ISO in the name of all seven organizations.
31. Taylor B.N. Kuyatt C.E. Guidelines for the Evaluation and Expression of Uncertainty in NIST Measurement Results 1994, and NIST Technical Note 1297 (National Institute of Standards and Technology, Gaithersburg, MD), see.
32. Frenkel M. Dong Q. Wilhoit R.C. Hall K.R. Int. J. Thermophys. 2001, 22:215. 10.1023/A:1006720022161, and.
33. Kazakov A. Muzny C.D. Kroenlein K. Diky V.V. Chirico R.D. Magee J.W. Abdulagatov I.M. Frenkel M. Int. J. Thermophys. 2012, 33:22. 10.1007/s10765-011-1107-7, and.
34. Frenkel M. Chirico R.D. Diky V.V. Muzny C.D. Kazakov A. Magee J.W. Abdulagatov I.M. Kroenlein K. Diaz-Tovar C. Kang J.W. Gani R. 2012, and NIST ThermoData Engine, NIST Standard Reference Database 103b-Pure Compounds, Binary Mixtures, and Chemical Reactions, version 7.0; Standard Reference Data Program (National Institute of Standards and Technology, Gaithersburg, MD).
35. See supplementary material at E-JPCRBU-42-002303 for lists of sources for the experimental values used in the critical data evaluation, plus the structural-group decomposition for all compounds evaluated in this research.
36. Cox J.D. Pilcher G. Thermochemistry of Organic and Organometallic Compounds 1970, and (Academic, London).
37. Diky V.V. Muzny C.D. Lemmon E.W. Chirico R.D. Frenkel M. J. Chem. Inf. Model. 2007, 47:1713. 10.1021/ci700071t, and.
38. Diky V.V. Chirico R.D. Kazakov A. Muzny C.D. Frenkel M. J. Chem. Inf. Model. 2009, 49:2883. 10.1021/ci900340k, and.
39. ASTM D240-09 Standard Test Method for Heat of Combustion of Liquid Hydrocarbon Fuels by Bomb Calorimeter, see.
40. Benson S.W. J. Am. Chem. Soc. 1996, 118:10645. 10.1021/ja962101w.
41. Benson S.W. J. Phys. Chem. A 1999, 103:11481. 10.1021/jp992971a.
42. Chickos J.S. Hyman A.S. Ladon L.H. Liebman J.F. J. Org. Chem. 1981, 46:4294. 10.1021/jo00334a040, and.
43. Ducros M. Gruson J.F. Sannier H. Thermochim. Acta 1980, 36:39. 10.1016/0040-6031(80)80109-2, and.
44. Majer V. Svoboda V. Pick J. Heats of Vaporization of Fluids 1989, and (Elsevier, Amsterdam).
45. 2000, MOL Format, see.
46. Press W.H. Teukolsky S.A. Vetterling W.T. Flannery B.P. Numerical Recipes: The Art of Scientific Computing 2007, and 3rd ed. (Cambridge University Press, New York).
47. Hukkerikar A.S. Kalakul S. Sarup B. Young D.M. Sin G. Gani R. J. Chem. Inf. Model. 2012, 52:2823. 10.1021/ci300350r, and.
48. Shtekher S.M. Skuratov S.M. Daukshas V.K. Levina R. Dokl. Akad. Nauk SSSR 1959, 127:812. and.
49. Moore G.E. Renquist M.L. Parks G.S. J. Am. Chem. Soc. 1940, 62:1505. 10.1021/ja01863a049, and.
50. Richards T.W. Davis H.S. J. Am. Chem. Soc. 1920, 42:1599. 10.1021/ja01453a011, and.
51. Zhang F.M. Xu G.D. Qu S.S. Acta Chim. Sin. 1990, 48:38. and.
52. Rogers D.W. Dejroongruang K. J. Chem. Thermodyn. 1988, 20:675. 10.1016/0021-9614(88)90018-3, and.
53. Rogers D.W. Dejroongruang K. J. Chem. Thermodyn. 1989, 21:1115. 10.1016/0021-9614(89)90099-2, and.
54. Yates K. McDonald R.S. J. Org. Chem. 1973, 38:2465. 10.1021/jo00954a012, and.
55. Moureu C. Andre E. Ann. Chim. Phys. 1914, 1:113. and.
56. Lamberti J.M. Wise P.H. J. Am. Chem. Soc. 1953, 75:4787. 10.1021/ja01115a050, and.
57. Serijan K.T. Wise P.H. J. Am. Chem. Soc. 1951, 73:4766. 10.1021/ja01154a086, and.
58. Serijan K.T. Wise P.H. J. Am. Chem. Soc. 1952, 74:365. 10.1021/ja01122a022, and.
59. Caves R.M. McLaughlin R.L. Wise P.H. J. Am. Chem. Soc. 1954, 76:522. 10.1021/ja01631a056, and.
60. Sharonov K.G. Mishentseva Y.B. Rozhnov A.M. Miroshnichenko E.A. Korchatova L.I. J. Chem. Thermodyn. 1991, 23:637. 10.1016/S0021-9614(05)80200-9, and.
61. Tavernier P. Lamouroux M. Mem. Poudres 1956, 38:65. and.
62. Tjebbes J. Acta Chem. Scand. 1962, 16:953. 10.3891/acta.chem.scand.16-0953.
63. Adriaanse N. Dekker H. Coops J. Recl. Trav. Chim. Pays-Bas 1965, 84:393. 10.1002/recl.19650840316, and.
64. Polschikova L.V. Savel'yanov V.P. Lebedev N.N. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1974, 17:144. and.
65. Matukova T.B. Panov M.Y. Vestn. Leningr. Univ., Ser. 4: Fiz. Khim. 1988, 3:117. and.
66. Butwill M.E. Rockenfeller J.D. Thermochim. Acta 1970, 1:289. 10.1016/0040-6031(70)80033-8, and.
67. Nilsson S.O. Wadso I. J. Chem. Thermodyn. 1986, 18:673. 10.1016/0021-9614(86)90070-4, and.
68. Hancock C.K. Watson G.M. Gilby R.F. J. Phys. Chem. 1954, 58:127. 10.1021/j150512a007, and.
69. Hall H.K. Baldt J.H. J. Am. Chem. Soc. 1971, 93:140. 10.1021/ja00730a025, and.
70. Swain H.A. Silbert L.S. Miller J.G. J. Am. Chem. Soc. 1964, 86:2562. 10.1021/ja01067a007, and.
71. Gerasimov P.A. Blokh E.L. Gubareva A.I. Gazhdiev S.N. Termodin. Org. Soedin. 1986:26. and.
72. Freedman B. Bagby M.O. Khoury H. J. Am. Oil Chem. Soc. 1989, 66:595. 10.1007/BF02885455, and.