The signature molecular descriptor. 5. The design of hydrofluoroether foam blowing agents using inverse-QSAR

Industrial and Engineering Chemistry Research

Volumn 44, Issue 23, 2005, Pages 8883-8891

  Weis, Derick C ^a   Faulon, Jean Loup ^b   LeBorne, Richard C ^c   Visco Jr , Donald P ^a  

^a Tennessee Technological University   (United States)

^b SANDIA NATIONAL LABORATORIES   (United States)

^c TENNESSEE TECHNOLOGICAL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOILING POINTS; MOLECULAR DESIGN;

ATOMS; BOILING LIQUIDS; FOAMS; INVERSE PROBLEMS; POLYURETHANES;

MOLECULAR STRUCTURE;

FOAM INJECTION;

EID: 28544440044     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie050330y     Document Type: Review

References (46)

1. Hawkins, D. M. The Problem of Overfitting. J. Chem. Inf. Comput. Sci. 2004, 44, 1-12.
2. Poling, B.; Prausnitz, J. M.; O'Connell, J. P. Properties of Gases and Liquids, 5th Edition; McGraw-Hill: New York, 2001.
3. Skvortsova, M. I.; Baskin, I. I.; Slovokhotova, O. L.; Palyulin, V. A.; Zefirov, N. S. Inverse problem in QSAR/QSPR studies for the case of topological indices characterizing molecular shape (Kier indices). J. Chem. Inf. Comput. Sci. 1993, 33, 630-634.
4. Gani, R.; Achenie, L. E. K.; Venkataeubramanian, V. Challenges and opportunities for CAMD. In Computer Aided Molecular Design: Theory and Practice; Achenie, L. E. K., Gani, R., Venkatasubramanian, V., Eds.; Elsevier: New York, 2003; pp 357-377.
5. Davidson, S. Fast Generation of an Alkane-Series Dictionary Ordered by Side-Chain Complexity. J. Chem. Inf. Comput. Sci. 2002, 42, 147-156.
6. Contreras, M. L.; Rozas, R.; Valdivia, R:, Exhaustive Generation of Organic Isomers. 3. Acyclic, Cyclic and Mixed Compounds. J. Chem. Inf. Comput. Sci. 1994, 34, 610-616.
7. Harper, P. M.; Gani, R.; Kolar, P.; Ishikawa, T. Computer-aided molecular design with combined molecular modeling and group contribution. Fluid Phase Equilib. 1999, 158-160, 337-347.
8. Venkatasubramanian, V.; Chan, K.; Caruthers, J. M. Computer-aided molecular design using genetic algorithms. Comput. Chem. Eng. 1994, 18 (9), 833-844.
9. Venkatasubramanian, V.; Chan, K.; Caruthers, J. M. Evolutionary Design of Molecules with Desired Properties Usjng the Genetic Algorithm. J. Chem. Inf. Comput. Sci. 1995, 35, 188-195.
10. Churi, N.; Achenie, L. E. K. Novel mathematical programming model for computer aided molecular design. Ind. Eng. Chem. Res. 1996, 35, 3788-3794.
11. Duvedi, A. P.; Achenie, L. E. K. Designing environmentally safe refrigerants using mathematical programming. Chem. Eng. Sci. 1996, 51, 3727-3739.
12. Siddhaye, S.; Camarda, K.; Southard, M.; Topp, E. Pharmaceutical product design using combinatorial optimization. Comput. Chem. Eng. 2004, 28, 425-434.
13. Chavali, S.; Lin, B.; Miller, D. C.; Camarda, K. Environmentally benign transition metal catalyst design using optimization techniques. Comput. Chem. Eng. 2004, 28, 605-611.
14. Hall, L. H.; Dailey, R. S.; Kier, L. B. Design of Molecules from Quantitative Structure-Activity Relationship Models. 3. Role of Higher Order Path Counts: Path 3. J. Chem. Inf. Comput. Sci. 1993, 33, 598-603.
15. Hall, L. H.; Fisk, J. B. Degree Set Generation for Chemical Graphs. J. Chem. Inf. Comput. Sci. 1994, 34, 1184-1189.
16. Hall, L. H.; Kier, L. B.; Frazer, J. W. Design of Molecules from Quantitative Structure-Activity Relationship Models. 2. Derivation and Proof of Information Transfert Relating Equations. J. Chem. Inf. Comput. Sci. 1993, 33, 148-152.
17. Kier, L. B.; Hall, L. H. The generation of molecular structures for a graph-based equation. Quant. Struct. - Act. Relat. 1994, 12, 383-388.
18. Bruggemann, R.; Pudenz, S.; Carlsen, L.; Sorensen, P. B.; Thomsen, M.; Mishra, R. K. The Use of Hasse Diagrams as a Potential Approach for Inverse QSAR. SAR QSAR Environ. Res. 2001, 11, 473-487.
19. Garg, S.; Achenie, L. E. K. Mathematical Programming Assisted Drug Design for Nonclassical Antifolates. Biotechnol. Prog. 2001, 17, 412-418.
20. Camarda, K. V.; Maranas, C. D. Optimization in Polymer Design Using Connectivity. Ind. Eng. Chem. Res. 1999, 38, 1884-1892.
21. Skvortsova, M. I.; Fedyaev, K. S.; Palyulin, V. A.; Zefirov, N. S. Molecular Design of Chemical Compounds with Prescribed Properties from QSAR Models Containing the Hosoya Index. Internet Electron. J. Mol. Des. 2003, 2, 70-85.
22. Faulon, J.-L.; Churchwell, C. J.; Visco, D. P., Jr. The Signature Molecular Descriptor. 2. Enumerating Molecules from Their Extended Valence Sequences. J. Chem. Inf. Comput. Sci. 2003, 43, 721-734.
23. Churchwell, C.; Rintoul, M. D.; Martin, S.; Visco, J., D. P.; Kotu, A.; Larson, R. S.; Sillerud, L. O.; Brown, D. C.; Faulon, J.-L. The signature molecular descriptor. 3. Inverse quantitative structure relationship of ICAM-1 inhibitory peptides. J. Mol. Graphics Modell. 2003, 22, 263-273.
24. Faulon, J.-L. Stochastic Generator of Chemical Structure. 1. Application to the Structure Elucidation of Large Molecules. J. Chem. Inf. Comput. Sci. 1994, 34, 1204-1218.
25. Faulon, J.-L. Stochastic Generator of Chemical Structure. 2. Using Simulated Annealing To Search the Space of Constitutional Isomers. J. Chem. Inf. Comput. Sci. 1996, 34, 731-740.
26. Faulon, J.-L.; Visco, D. P., Jr.; Pophale, R. S. The Signature Molecular Descriptor. 1. Extended Valence Sequences and Topological Indices. J. Chem. Inf. Comput. Sci. 2003, 43, 707-720.
27. Visco, J. D. P.; Pophale, R. S.; Rintoul, M. D.; Faulon, J.-L. Developing a methodology for an inverse quantitative structure activity relationship using the signature molecular descriptor. J. Mol. Graphics Modell. 2002, 20, 429-438.
28. Hall, L. H. MOLCONN-Z. Hall Associates Consulting: Quincy, MA, 1991.
29. Martin, S.; Roe, D.; Faulon, J. L. Predicting protein-protein interactions using signature products. Bioinformatics 2004, 20, 1-9.
30. Sekiya, A.; Misaki, S. The potential of hydrofluoroethers to replace CFCs, HCFCs and PFCS. J. Fluorine Chem. 2000, 101, 215-221.
31. Decaire, B. R.; Pham, H. T.; Richard, R. G.; Shankland, I. R. Blowing Agents: The Next Generation. J. Cell. Plast. 1994, 30, 11-33.
32. Faulon, J. L. http://www.cs.sandia.gov/~jfaulon/SIGNATURE/SIGNATURE.html.
33. Contejean, E.; Devie, H. An efficient incremental algorithm for solving systems of linear Diophantine equations. J. Inf. Comput. 1994, 113, 143-172.
34. Clausen, M.; Fortenbacher, A. Efficient solution of linear Diophantine equations. J. Symbolic Comput. 1989, 8, 201-216,
35. Draper, N. R.; Smith, H. Applied Regression Analysis, 2nd Edition; Wiley: New York, 1981.
36. Williams, D. J.; Bogdan, M. C.; Parker, R. C.; Knopeck, G. M. Update on the Development of HFC-245fa as a Liquid HFC Blowing Agent. In Proceedings of the Polyurethanes 1995 Conference, September 26-29, 1995; pp 2-9.
37. Moore, G. G. I.; Flynn, R. M.; Guerra, M. A.; Owens, J. G. Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application, U.S. Patent No. 6,204,299 B1, March 20, 2001.
38. Musso, E.; Basile, G. A.; Girolomoni, S. Hydrofluoropolyether-based azeotropic or near azeotropic compositions, European Patent No. EP 0 980 910 A2, February 23, 2000.
39. Nyberg, J. M.; Mainz, E. L. Isopropyl chloride with hydroflurocarbon or hydrofluoroether as foam blowing agents, U.S. Patent No. 6,646,020 B2, November 11, 2003.
40. Bogdan, M.; Williams, D. A Quality, Cost Effective, Flammable HFC Blowing Agent Alternative for Construction Foam Applications: Blends of HFC-245fa and Hydrocarbons. In Proceeedings of the Polyurethanes 2000 Conference; pp 179-182.
41. Murata, J.; Yamashita, S.; Akiyama, M.; Katayama, S.; Haiaki, T.; Sekiya, A. Vapor pressures of hydrofluoroethers. J. Chem. Eng. Data 2002, 47, 911-915.
42. Sako, T.; Sato, M.; Nakazawa, N.; Oowa, M.; Yasumoto, M.; Ito, H.; Yamashita, S. Critical properties of fluorinated ethers. J. Chem. Eng. Data 1996, 41, 802-805.
43. Horvath, A. Boiling points of halogenated organic compounds. Chemosphere 2001, 44, 897-905.
44. Sako, T.; Yasumoto, M.; Sato, M.; Kitao, O.; Ishiguro, K.; Kato, M. Measurement of critical properties of fluorinated ethers and amines. Fluid Phase Equilib. 1998, 144, 113-117.
45. Park, J. D.; Lycan, W. R.; Lacher, J. R. The addition of products of trifluoroethylene. J. Am. Chem. Soc. 1951, 73, 711-712.
46. Takada, N.; Matsuo, S.; Tanaka, Y.; Sekiya, A. Gaseous thermal conductivities of new hydrofluoroethers (HFEs). J. Fluorine Chem. 1998, 91, 81-85.