Molecular design using quantum chemical calculations for property estimation

Industrial and Engineering Chemistry Research

Volumn 43, Issue 13, 2004, Pages 3419-3432

  Lehmann, Andreas ^a   Maranas, Costas D ^a  

^a Pennsylvania State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENVIRONMENTAL PROTECTION; FLUOROCARBONS; GENETIC ALGORITHMS; QUANTUM THEORY; REFRIGERANTS;

MOLECULAR DESIGN; SOLVENT DESIGN;

MOLECULAR DYNAMICS;

FLUORINATED HYDROCARBON;

CHEMICAL COMPOSITION;

ALGORITHM; ARTICLE; CHEMICAL STRUCTURE; GEOMETRY; MOLECULAR MODEL; QUANTUM CHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 2942659202     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie030120q     Document Type: Article

References (78)

1. Churie, N.; Achenie, L. Novel Mathematical Programming Model for Computer Aided Molecular Design. Ind. Eng. Chem. Res. 1996, 35, 3788.
2. Maranas, C. Optimal Computer-Aided Molecular Design: A Polymer Case Study. Ind. Eng. Chem. Res. 1996, 35, 3403.
3. Venkatasubramanian, V.; Chan, K; Caruthers, J. Computer-Aided Molecular Design Using Genetic Algorithms. Comput. Chem. Eng. 1994, 18 (9), 833.
4. Gani, R.; Nielsen, B.; Fredenslund, A. A Group Contribution Approach to Computer Aided Molecular Design. AIChE J. 1991, 37 (9), 1318.
5. van Krevelen, D. W. Properties of Polymers: their correlation with chemical structure; their numerical estimation and prediction from additive group contributions, 3rd ed.; Elsevier: Amsterdam, The Netherlands, 1990.
6. Joback, K.; Reid, R. Estimation of Pure-Component Properties From Group Contributions. Chem. Eng. Commun. 1987, 57, 223.
7. Fredenslund, A.; Gmehling, J.; Rasmussen, P. Vapor-Liquid Equilibria Using UNIFAC; Elsevier: Amsterdam, The Netherlands, 1977.
8. Lin, S.; Sandler, S. Infinite Dilution Activity Coefficients from Ab Initio Solvation Calculations. AIChE J. 1999, 45 (12), 2606.
9. Poling, B.; Prausnitz, J.; O'Connel, J. The Properties of Gases and Liquids, 5th ed.; McGraw-Hill: New York, 2001.
10. Levine, I. Quantum Chemistry, 5th ed.; Prentice Hall: Engelwood Cliffs, NJ, 2000.
11. Szabo, A.; Ostlund, N. Modern Quantum Chemistry; McGraw-Hill: New York, 1989.
12. Parr, R.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
13. Labanowski, J. Simplified Introduction to Ab Initio Basis Sets; Ohio Supercomputer Center: Columbus, OH, 1996 [e-mail, jkl@osc.edu, jkl@ohstpy.bitnet; URL(several), http://www.ccl.net/cca/documents/basis-sets/ basis.html].
14. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Robb, G. E. S. M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; R. E. S.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Tomasi, O. F. J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
15. Gaussian 98, User's Reference, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1994-1999.
16. Pople, J.; Gordon, M. Molecular orbital theory of the electronic structure of organic compounds. I. Substituent effects and dipole moments. J. Am. Chem. Soc. 1967, 89 (17), 4253.
17. Minoux, M. Mathematical Programming-Theory and Algorithms; Wiley: New York, 1986.
18. Holland, J. Adaptation in Natural and Artificial Systems; University of Michigan Press: Ann Arbor, MI, 1975.
19. Michalewicz, Z. Genetic Algorithms + Data Structures = Evolution Programs; Springer-Verlag: Berlin, 1994.
20. Goldberg, D. Genetic Algorithms in Search, Optimization, and Machine Learning; Addison-Wesley: Reading, MA, 1989.
21. Curtiss, L.; Raghavachari, K.; Redfern, P.; Pople, J. Assessment of Gaussian-2 and Density Functional Theories for the computation of Enthalpies of Formation. J. Chem. Phys. 1997, 106 (3), 1063.
22. Chase, M.; Davies, C.; Downey, J. R.; Frurip, D.; McDonald, R.; Syverud, A. JANAF Thermochemical Table. Journal of Physical and Chemical Reference Data, Supplement No. 1, 3rd ed.; 1985; p 14.
23. Bauschlicher, C. A comparison of the accuracy of different functionals. Chem. Phys. Lett. 1995, 246, 40.
24. Curtiss, L.; Raghavachari, K.; Trucks, G.; Pople, J. Gaussian-2 Theory for Molecular Energies of First- and Second-row Compounds. J. Chem. Phys. 1991, 94 (11), 7221.
25. Camarda, K.; Maranas, C. Optimization in Polymer Design Using Connectivity Indices. Ind. Eng. Chem. Res. 1999, 38, 1884.
26. Raman, V.; Maranas, C. Optimization in product design with properties correlated with topological indeces. Comput. Chem. Eng. 1998, 22 (6), 747.
27. GAMS: A User's Guide; GAMS Development Corp.: Washington, DC, 1998.
28. GAMS: The Solver Manuals; GAMS Development Corp.: Washington, DC, 1998.
29. Hradetzky, G.; Hammerl, I.; Bittrich, H.-J.; Wehner, K.; Kisan, W. Selective Solvents, Data on dimethylformamide-N-methylcaprolactam-N- methylpyrrolidone; Physical Sciences Data 31; Elsevier: Amsterdam, The Netherlands, 1989.
30. van Leeuwen, C.; Hermens, J. Risk Assessment of Chemicals: An Introduction; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995.
31. Lin, S.; Sandler, S. Prediction of Octanol-Water Partition Coefficients Using a Group Contribution Solvation Model. Ind. Eng. Chem. Res. 1999, 38, 4081.
32. Abrams, D.; Prausnitz, J. Statistical Thermodynamics of Liquid Mixtures: A New Expression for the Excess Gibbs Energy of Partly or Completely Miscible Systems. AIChE J. 1975, 21 (1), 116.
33. Tomasi, J.; Persico, M. Molecular Interactions in Solution: An Overview of Methods Based on Continuous Distributions of the Solvent. Chem. Rev. 1994, 94, 2027.
34. Schmidt, M.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. General Atomic and Molecular Electronic Structure System. J. Comput. Chem. 1993, 14, 1347.
35. Dunning, T., Jr.; Hay, P. Gaussian Basis Sets for Molecular Calculations. In Methods of Electronic Structure Theory; Shaefer, H., III, Ed.; Plenum Press: New York, 1977; pp 1-27.
36. Mennucci, B. (University of Pisa). Personal communication, 2002.
37. Klamt, A. Conductor-Like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena. J. Phys. Chem. 1995, 99 (7), 2224.
38. Klamt, A.; Schüürmann, G. COSMO: A New Approach to Dielectric Screening in Solvents with Explicit Expressions for the Screening Energy and its Gradient. J. Chem. Soc., Perkin Trans. 2 1993, 5, 799.
39. Eckert, F.; Klamt, A. Fast Solvent Screening via Quantum Chemistry: COSMO-RS Approach. AIChE J. 2002, 48 (2), 369.
40. Perry, R., Ed. Perry's Chemical Engineers' Handbook, 6th ed.; McGraw-Hill: New York, 1984.
41. Sandler, S. I. Quantum mechanics: a new tool for engineering thermodynamics. Fluid Phase Equilib. 2003, 210, 147.
42. Trinajsticć, N. Chemical Graph Theory, 2nd ed.; CRC Press: Boca Raton, FL, 1992.
43. Floudas, C. Nonlinear and Mixed-Integer Optimization; Oxford University Press: New York, 1995.
44. Lias, S.; Karpas, Z.; Liebman, J. Halomethylenes: effects of halogen substitution on absolute heats of formation. J. Am. Chem. Soc. 1985, 107, 6089.
45. 2. J. Phys. Chem. 1958, 62, 1043.
46. Goy, C.; Lord, A.; Pritchard, H. Kinetics and thermodynamics of the reaction between iodine and fluoroform and the heat of formation of trifluoromethyl iodide. J. Phys. Chem. 1967, 71, 1086.
47. Neugebauer, C.; Margrave, J. Heats of formation of the fluoromethanes and fluoroethylenes; Technical Report; 1957; pp 1-45.
48. Chase, M., Jr. NIST-JANAF Thermochemical Tables. Journal of Physical and Chemical Reference Data, Monograph 9; 1998; p 1.
49. Selected Values of Properties of Chemical Compounds; Data Project; Thermodynamics Research Center, Texas A&M University: College Station, TX, 1983.
50. Kolesov, V.; Papina, T. Standard enthalpy of formation of vinyl fluoride. J. Phys. Chem. (Engl. Transl.) 1970, 44, 611.
51. Wagman, D.; Evans, W.; Parker, V.; Schumm, R.; Halow, I.; Bailey, S. Churney, K.; Nuttall, R. NBS Tables of Chemical Thermodynamic Properties. J. Phys. Chem. Ref. Data, Suppl. No. 2 1982.
52. Kolesov, V.; Martynov, A.; Shtekher, S.; Skuratov, S. Standard enthalpies of formation of 1,1-difluoroethylene and of trifluoroethylene. Russ. J. Phys. Chem. (Engl. Transl.) 1962, 36, 1118.
53. Neugebauer, C.; Margrave, J. The heats of formation of tetrafluoroethylene, tetrafluoromethane and 1,1-difluoroethylene. J. Phys. Chem. 1956, 60, 1318.
54. Kolesov, V.; Zenkov, I.; Skuratov, S. The standard enthalpy of formation of tetrafluoroethylene. Russ. J. Phys. Chem. (Engl. Transl.) 1962, 36, 45.
55. Wartenberg, H. V.; Schiefer, J. Bildungswärmen von Fluor-Chlor-Kohlenstoff-Verbindungen. Z. Anorg. Chem. 1955, 278, 326.
56. Kirkbride, F.; Davidson, F. Heats of formation of gaseous fluoro- and fluorochloro-carbons. Nature (London) 1954, 174, 79.
57. TRC Thermodynamic Tables-Non-Hydrocarbons; Thermodynamics Research Center, Texas A&M University: College Station, TX, 1989.
58. Thermochemical Data and Structures of Organic Compounds; Thermodynamics Research Center, Texas A&M University: College Station, TX, 1994; Vol. 1.
59. Kolesov, V.; Papina, T. Thermochemistry of Haloethanes. Russ. Chem. Rev. 1983, 52, 425.
60. 2I + HI. The carbon-hydrogen bond dissociation energy in 1,1,1-trifluoroethane and the heat of formation of the 2,2,2-trifluoroethyl radical. J. Phys. Chem. 1974, 78, 2315.
61. Kolesov, V.; Martynov, A.; Skuratov, S. Standard enthalpy of formation of 1,1,1-trifluoroethane. Russ. J. Phys. Chem. (Engl. Transl.) 1965, 39, 223.
62. Selected Values of Properties of Chemical Compounds; Data Project (loose-leaf data sheets, extant); Thermodynamics Research Center, Texas A&M University: College Station, TX, 1980.
63. Chen, S.; Rodgers, A.; Chao, J.; Wilhoit, R.; Zwolinski, B. Ideal Gas Thermodynamic Properties of Six Fluoroethanes. J. Phys. Chem. Ref. Data 1975, 4, 441.
64. Walker, L.; Sinke, G.; Perettie, D.; Janz, G. Enthalpy of formation of trifluoroacetonitrile. J. Am. Chem. Soc. 1970, 92, 4525.
65. 6. Trans. Faraday Soc. 1967, 63, 1394.
66. Sinke, G. The heat of reaction of nitrogen trifluoride and hexafluoroethane. J. Phys. Chem. 1966, 70, 1326.
67. Alfassi, Z.; Golden, D.; Benson, S. The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the Cd-(H)(X) group. J. Chem. Thermodyn. 1973, 5, 411.
68. Kolesov, V.; Martinov, A.; Skuratov, S. Standard enthalpies of formation of 1,1,1-trifluoropropene. Zh. Fiz. Khim. 1967, 41, 913.
69. Cox, J.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: New York, 1970; pp 1-636.
70. Papina, T.; Kolesov, V.; Golovanova, Y. Standard enthalpies of formation of 1,2-Dichlorohexafluoropropane and hexafluoropropane. Russ. J. Phys. Chem. (Engl. Transl.) 1987, 61, 1168.
71. Williamson, A.; LeBreton, P.; Beauchamp, J. Photoionization mass spectrometry of 2-fluoropropane and 2,2-difluoropropane. A novel determination of the proton affinity of vinyl fluoride and 1,1-difluoroethylene. J. Am. Chem. Soc. 1976, 98, 2705.
72. Pedley, J.; Naylor, R.; Kirby, S. Thermochemical Data of Organic Compounds; Chapman and Hall: London, 1986.
73. Kolesov, V.; Talakin, O.; Skuratov, S. Standard enthalpy of formation of perfluoropropane and enthalpies of formation of normal perfluoroalkanes. Vestn. Mosk. Univ. Khim. 1967, 22, 38.
74. Sangster, J. Octanol-Water Partition Coefficients; Wiley and Sons: New York, 1997.
75. Suzuki, T.; Kudo, Y. Automatic log P estimation based on combined additive modeling methods. J. Comput.-Aided Mol. Des. 1990, 4, 155.
76. Sangster, J. Octanol-Water Partition Coefficients of Simple Organic Compounds. J. Phys. Chem. Ref. Dat. 1989, 18 (3), 1111.
77. Isnard, P.; Lambert, S. Aqueous Solubility and n-Octanol/Water Partition Coefficient Correlations. Chemosphere 1989, 18, 1837.
78. Howard, P., Meylan, W., Eds. Handbook of Physical Properties of Organic Chemicals; Lewis Publishers: Boca Raton, FL, 1997.