Study of the carbamate stability of amines using ab initio methods and free-energy perturbations

Industrial and Engineering Chemistry Research

Volumn 45, Issue 8, 2006, Pages 2497-2504

  Da Silva, Eirik F ^a   Svendsen, Hallvard F ^a  

^a NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; FREE ENERGY; GAS ABSORPTION; MATHEMATICAL MODELS; MONTE CARLO METHODS; NUCLEAR MAGNETIC RESONANCE; PERTURBATION TECHNIQUES;

AB INITIO METHODS; CARBAMATES; FREE ENERGY PERTUBATIONS; SOLVATION;

AMINES;

AMINES; CARBON DIOXIDE; FREE ENERGY; GAS ABSORPTION; MATHEMATICAL MODELS; MONTE CARLO METHODS; NUCLEAR MAGNETIC RESONANCE; PERTURBATION TECHNIQUES;

EID: 33646230315     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie050501z     Document Type: Conference Paper

References (36)

1. 2 Separation from Flue Gas Streams. Greenhouse Gas Control Technol., Proc. Int. Conf., 4th 1999, 35.
2. 2 Recovery by the Chemical Absorption Method in Power Plant. Greenhouse Gas Control Technol., Proc. Int. Conf., 4th 1999, 71.
3. Reddy, S.; Scherffius, J.; Freguia, S.; Roberts, C. Fluor's Econamine FG Plus Technology. Presented at the Second International Conference on Carbon Sequestration, U.S. Department of Energy (DOE), Alexandria, VA, 2003.
4. 2 and alkanolamines both in aqueous and nonaqueous solutions. An overview. Chem. Eng. Commun. 1996, 144, 113.
5. Perrin, D. D. Dissociation Constants of Organic Bases in Aqueous Solution. Butterworths: London, 1965 (and Supplement, 1972).
6. 2 Removal from Gases. Ind. Eng. Chem. Fundam. 1983, 22, 239.
7. 2 interaction investigated by NMR and IR Spectroscopies. Chem. Lett. 2003, 32, 344.
8. 2O-system by NMR spectroscopy. Chem. Lett. 1996, 25, 777.
9. a Values of Amines Using ab Initio Methods and Free-Energy Perturbations. Ind. Eng. Chem. Res. 2003, 42, 4414.
10. 2 with dimethylamine. J. Mol. Struct. 1997, 404, 105.
11. 2 Interactions. J. Am. Chem. Soc. 1988, 110, 6947.
12. Ohno, K.; Inoue, Y.; Yoshida, H.; Matsuura, H. Reaction of Aqueous 2-(N-Methylamino)ethanol Solutions with Carbon Dioxide. Chemical Species and Their Conformations Studied by Vibrational Spectroscopy and ab Initio Theories. J. Phys. Chem. A 1999, 103, 4283.
13. 2 and Alkanolamines. Ind. Eng. Chem. Res. 2004, 43, 3413.
14. Lukin, O.; Leszczynski, J. Rationalizing the Strength of Hydrogen-Bonded Complexes. Ab Initio HF and DFT Studies. J. Phys. Chem. A 2002, 106, 6775-6782.
15. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, 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.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
16. PC SPARTAN Version 1.0.7, Wavefunction, Inc., Irvine, CA.
17. Wiberg, K. B.; Clifford, S.; Jorgensen, W. L.; Frisch, M. J. Origin of the Inversion of the Acidity Order for Haloacetic Acids on going from the Gas phase to Solution. J. Phys. Chem. A 2000, 104, 7625.
18. Rizzo, R. C.; Jorgensen, W. L. OPLS All-Atom Model for Amines: Resolution of the Amine Hydration Problem. J. Am. Chem. Soc. 1999, 121, 4827.
19. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids. J. Am. Chem. Soc. 1996, 118, 11225.
20. Harris, J. G.; Yung, K. H. Carbon dioxide's liquid-vapor coexistence curve and critical properties as predicted by a simple molecular model. J. Phys. Chem. 1995, 99, 12021.
21. Hawkins, G. D.; Zhu, T.; Li, J.; Chambers, C. C.; Giesen, D. J.; Liotard, D. A.; Cramer, C. J.; Truhlar, D. G. Universal Solvation Models. In Combined Quantum Mechanical and Molecular Mechanical Methods; Gao, J., Thompson, M. A., Eds.; ACS Symposium Series 712; American Chemical Society: Washington, DC, 1998; pp 201-219.
22. Li, J.; Zhu, T.; Cramer, C. J.; Truhlar, D. G. New Class IV Charge Model for Extracting Accurate Partial Charges from Wave Functions J. Phys. Chem. A 1998, 102, 1820-1831.
23. Xidos, J. D.; Li, J.; Zhu, T.; Hawkins, G. D.; Thompson, J. D.; Chuang, Y.-Y.; Fast, P. L.; Liotard, D. A.; Rinaldi, D.; Cramer, C. J.; Truhlar, D. G. Gamesol-version 3.1, University of Minnesota, Minneapolis, MN, 2002.
24. (Based on the General Atomic and Molecular Electronic Structure System (GAMESS), as described in Schmidt, M. W.; 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. J. Comput. Chem. 1993, 14, 1347.)
25. Cramer, C. J. Essentials of Computational Chemistry; Wiley: New York, 2002.
26. Sigfridsson, E.; Ryde, U. Comparison of Methods for Deriving Atomic Charges from the Electrostatic Potential and Monomers. J. Comput. Chem. 1998, 19, 377.
27. Jorgensen, W. L. BOSS, Version 4.3, Yale University, New Haven, CT, 1989.
28. Jorgensen, W. L.; Ravimohan, C. Monte Carlo simulation of differences in free energies of hydration. J. Chem. Phys. 1985, 83, 3050.
29. Cances, M. T.; Mennucci, V.; Tomasi, J. A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics. Chem. Phys. 1997, 707, 3032.
30. Littel, R. J.; Bos, M.; Knoop, G. J. Dissociation constants of some alkanolamines at 293, 303, 318, and 333 K. J. Chem. Eng. Data 1990, 55, 276.
31. Bishnoi, S. Dissertation, University of Texas, Austin, TX, 2000.
32. Sharma, M. M. Kinetics of Reactions of Carbonyl Sulphide and Carbon Dioxide with Amines. Trans. Faraday Soc. 1965, 61, 681.
33. Alejandro, J.; Rivera, J. L.; Mora, M. A.; de la Garza, V. Force Field of Monoethanolamine. J. Phys. Chem. B 2000, 104, 1332.
34. Tubergen, M. J.; Torok, C. R.; Lavrich, R. J. Effect of solvent on molecular conformation: Microwave spectra and structures of 2-aminoethanol van der Waals complexes. J. Chem. Phys. 2003, 119, 8397.
35. Silva, C. F. P.; Duarte, M. L. T. S.; Fausto, R. A concerted SCFMO ab initio and vibrational spectroscopic study of the conformational isomerism in 2-aminoethanol. J. Mol. Struct. 1999, 483, 591.
36. Winget, P.; Hawkins, G. D.; Cramer, C. J.; Truhlar, D. G. Prediction of Vapor Pressures from Selv-Solvation Free Energies Calculated by the SM5 Series of Universal Solvation Models. J. Phys. Chem. B 2000, 104, 4726.