Computational study of the aminolysis of anhydrides: Effect of the catalysis to the reaction of succinic anhydride with methylamine in gas phase and nonpolar solution

Journal of Physical Chemistry A

Volumn 112, Issue 23, 2008, Pages 5224-5235

  Petrova, Tetyana ^a,b   Okovytyy, Sergiy ^a,b   Gorb, Leonid ^a   Leszczynski, Jerzy ^a  

^a JACKSON STATE UNIVERSITY   (United States)

^b OLES HONCHAR DNIPRO NATIONAL UNIVERSITY   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACIDS; ACTIVATION ENERGY; AMINATION; AMINES; CATALYSIS; CONTINUUM MECHANICS; ELECTRIC POWER PLANTS; ELECTRONIC STRUCTURE; MECHANISMS; MINE FLOODING; ORGANIC COMPOUNDS; PERTURBATION TECHNIQUES; PROBABILITY DENSITY FUNCTION; PROTON TRANSFER; PROTONS; SOLVENTS;

AB-INITIO CALCULATIONS; ACTIVATION BARRIERS; AMINOLYSIS; AMINOLYSIS REACTIONS; ATOMIC MOVEMENTS; B3LYP/6-31G; BASIS SETS; BIFUNCTIONAL; CCSD; COMPUTATIONAL STUDIES; CONCERTED MECHANISM; DENSITY-FUNCTIONAL; ELECTRONIC STRUCTURE THEORY; GAS-PHASE; GENERAL ACID CATALYSIS; GENERAL BASE CATALYSIS; INTRINSIC REACTION COORDINATE; NON-POLAR; PLESSET PERTURBATION THEORY; POLARIZED CONTINUUM MODEL; REACTION PATHWAYS; SECOND ORDERS; SINGLE POINT; SOLVENT EFFECTS; STEPWISE MECHANISM; SUCCINIC ANHYDRIDES; TRANSITION STATES; TRANSITION VECTORS; TRANSITION-STATE STRUCTURES;

DENSITY FUNCTIONAL THEORY;

EID: 84961979134     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp7102897     Document Type: Article

References (41)

1. Bunnett, J. F.; Davis, G. T. J. Am. Chem. Soc. 1960, 82, 665.
2. Jencks, W. P.; Carriuolo, J. J. Am. Chem. Soc. 1960, 82, 675.
3. Blackburn, G. M.; Jencks, W. P. J. Am. Chem. Soc. 1968, 90, 2638.
4. Jencks, W. P.; Gilchrist, M. J. Am. Chem. Soc. 1966, 88, 104.
5. Bruice, T. C.; Mayahi, M. F. J. Am. Chem. Soc. 1960, 82, 3067.
6. Bruice, T. C.; Donzel, A.; Huffman, R. W.; Butler. A. R. J. Am. Chem. Soc. 1967, 89, 2106.
7. Rogers, G. A.; Bruice, T. C. J. Am. Chem. Soc. 1973, 95, 4452.
8. Rogers, G. A.; Bruice, T. C. J. Am. Chem. Soc. 1974, 96, 2473.
9. Bruice, T. C.; Benkovic, S. J. J. Bioorganic Mechanisms; W.A. Benjamin Inc.: New York, 1966; Vol. 1.
10. Jencks, W. P. Catalysis in Chemistry and Enzymology; McGraw-Hill: New York, 1969.
11. Williams, A. Acc. Chem. Res. 1989, 22, 387.
12. Yang, W.; Drueckhammer, D. G. Org. Leet. 2000, 2, 4133.
13. Ilieva, S.; Galabov, B.; Musaev, D. G.; Morokuma, K.; Schaefer, H. F., III J. Org. Chem. 2003, 68, 1496.
14. Cox, M. M.; Jencks, W. P. J. Am. Chem. Soc. 1981, 103, 572.
15. Satterthwait, A. C.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 7018.
16. Fox, J. P.; Page, M. I.; Satterthwait, A. C.; Jencks, W. P. J. Am. Chem. Soc. 1972, 94, 4731.
17. Yang, C. C.; Jencks, W. P. J. Am. Chem. Soc. 1988, 110, 2972.
18. O'Hair, R. A. J.; Androutsopoulos, N. K. Org. Lett. 2000, 2, 2567.
19. Kim, C. K.; Li, H. G.; Lee, H. W.; Sohn, C. K.; Chun, Y. I.; Lee, I. J. Phys.Chem. A 2000, 104, 4069.
20. Zipse, H.; Wang, L.; Houk, K. N. Liebigs Ann. 1996, 1511.
21. Wang, L.; Zipse, H. Liebigs Ann. 1996, 1501.
22. Oie, T.; Loew, G. H.; Burt, S. K.; Binkley, J. S.; McErloy, R. D. J. Am. Chem. Soc. 1982, 104, 6169.
23. Singleton, D. A.; Merrigan, S. R. J. Am. Chem. Soc. 2000, 122, 11035.
24. Marlier, J. F.; Haptonsall, B. A.: Johnson, A. J.; Sacksteder, K. A. J. Am. Chem. Soc. 1997, 119, 8838.
25. Kruger, H. G. J. Mol. Struct.(Theochem) 2002, 577, 281.
26. Yamabe, S.; Ishikawa, T. J. Org. Chem. 1997, 62, 7049.
27. Kasyan, A. O.; Krischik, O. V.; Krasnovskaya, O.Yu.; Kasyan, L. I. Rus. J.Org.Chem. 1998, 12, 1802.
28. Bartnicka, H.; Smagowski, H. Pol. J. Chem. 1992, 66. 1277.
29. Bartnicka, H.; Smagowski, H. Pol. J. Chem. 1992, 66, 1295.
30. Patent No.: US 6.479.264 B1, Nov. 12, 2002.
31. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
32. For conversion from 1 atm standard state to 1 mol/L standard state, the following contributions need to be added to standard enthalpy, entropy, and Gibbs free energy: - RT, - R - R InR′T, and RTIn R′T, where R′ is the value of R in L·atm/mol·K (ref 37). For a reaction with A + B = C stoichiometry (such as the uncatalyzed aminolysis mechanism, Figure 1), the corrections for ΔH‡, ΔS‡, and ΔG‡ are RT, R + R In R′T, and RT In R′T. At 298 K, the corrections amount to 0.59 and - 1.90 kcal/mol for ΔH‡ and ΔG‡ and +8.34 eu for ΔS‡ (ref 38). For a reaction with A + B + C = D stoichiometry (such as the aminolysis mechanism, catalyzed by second methylamine, Figure 4), the corrections for ΔHΔ, ΔS‡ and ΔG‡ are 2RT, 2(R + R In R′T), and 2RT In R′T. At 298 K, the corrections amount to 1.18 and - 3.79 kcal/mol for ΔH‡ and ΔG‡ and +16.68 eu for ΔS‡.
33. (a) Fukui, K. J. Phys. Chem. 1970, 74, 4161.
34. (b) Fukui, K. Acc Chem. Res. 1981, 14, 363.
35. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
36. (b) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1990, 94, 5523.
37. (a) Deng, L.; Ziegler, T.; Fan, L. J. Chem. Phys. 1993, 99, 3822.
38. (b) Deng, L.; Ziegler, T. Int. J. Quantum Chem. 1994, 52, 731.
39. Miertus, S.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1981, 55, 117.
40. Benson, S. Thermochemical Kinetics; Wiley: New York, 1968; p 8.
41. Rastelli, A.; Bagatti, M.; Gandolfi, R. J. Am. Chem. Soc. 1995, 117, 4965.