Theoretical study of the iodination of methoxybenzene by iodine monochloride

Journal of Physical Organic Chemistry

Volumn 18, Issue 7, 2005, Pages 625-631

  Wei, Yu ^a   Wang, Bing Wu ^a   Hu, Shao Wen ^a   Chu, Tai Wei ^a   Tang, Ling Tian ^a   Liu, Xin Qi ^a   Wang, Yi ^a   Wang, Xiang Yun ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

Density functional theory; Iodination; Iodine monochloride; Methoxybenzene; Solvent effects; Transition state

Indexed keywords

ACTIVATION ENERGY; BENZENE; COMPLEXATION; ELECTRON TRANSITIONS; HYDROGEN BONDS; IODINE COMPOUNDS; PROBABILITY DENSITY FUNCTION;

IODINATION; IODINE MONOCHLORIDE; METHOXYBENZENE; SOLVENT EFFECTS; TRANSITION STATE;

REACTION KINETICS;

EID: 19844373860     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.911     Document Type: Article

References (44)

1. Lowery TH, Richardson KS. Mechanism and Theory in Organic Chemistry (3rd edn). Harper and Row: New York, 1987; 623.
2. Taylor R. Electrophilic Aromatic Substitution. Wiley: New York, 1990; 31.
3. March J. Advanced Organic Chemistry. Wiley: New York, 1992; 501.
4. Hubig SM, Kochi JK. J. Am. Chem. Soc. 2000; 122: 8279-8288.
5. Vasilyev AV, Lindeman SV, Kochi JK. New J. Chem. 2002; 26: 582-592.
6. Lenoir D. Angew. Chem. Int. Ed. 2003; 42: 854-857.
7. Lambourne LJ, Robertson PW. J. Chem. Soc. 1947; 69:1167-1168.
8. Keefer RM, Andrews LJ. J. Am. Chem. Soc. 1950; 72: 5170.
9. Bennett FW, Sharpe AG. J. Chem. Soc. 1950; 72: 1383-1384.
10. Papa D, Ginsberg HF, Lederman I, DeCamp V. J. Am. Chem. Soc. 1953; 75: 1107-1110.
11. Jones B, Richardson EN. J. Chem. Soc. 1953; 75: 713-715.
12. Andrews LJ, Keefer RM. J. Am. Chem. Soc. 1957; 79: 1412-1416.
13. Berliner E. J. Am. Chem. Soc. 1956; 78: 3632-3637.
14. Olah G, Pavlath A, Varsanyi G. J. Chem. Soc. 1957: 79: 1823-1829.
15. Hubig SM, Jung W, Kochi JK. J. Org. Chem. 1994; 59: 6233-6244.
16. Turner DE, O'Malley RF, Sardella DJ, Barinelli LS, Kaul P. J. Org. Chem. 1994; 59: 7335-7340.
17. Eberson L, Hartshorn MP, Radner F, Persson O. J. Chem. Soc., Perkin Trans. 2 1998; 59-70.
18. Zhong DP, Bernhardt TM, Zewail AH. J. Phys. Chem. A 1999; 103: 10093-10117.
19. Fabbrini M, Galli C, Gentili P, Macchitella D, Petride H. J. Chem. Soc., Perkin Trans. 2 2001; 1516-1521.
20. Ammal SSC, Ananthavel SP, Venuvanalingam P, Hedge MS. J. Phys. Chem. A 1998; 102: 532-536.
21. Su JT, Zewail AH. J. Phys. Chem. A 1998; 102: 4082-4099.
22. Grozema PC, Zijlstra RWJ, Swart M, Van Duijnen PT. Int. J. Quantum Chem. 1999; 75: 709-723.
23. Smith WB. J. Phys. Org. Chem. 2002; 15: 347-352.
24. Smith WB. J. Phys. Org. Chem. 2003; 16: 34-39.
25. Heidrich D. Angew. Chem. Int. Ed. 2002; 41: 3208-3210.
26. Litao Ch, Heming X, Jijun X, Xuedong G. J. Phys. Chem. A 2003; 107: 11440-11444.
27. Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785-789.
28. Miehlich B, Savin A, Stoll H, Preuss H. Chem. Phys. Lett. 1989; 157: 200-206.
29. Sosa C, Lee C. J. Chem. Phys. 1993; 98: 8004-8011.
30. Ruiz E, Salahub D, Vela A. J. Am. Chem. Soc. 1995; 117: 1141-1142.
31. Bally T, Sastry GN. J. Phys. Chem. A 1997; 101: 7923-7925.
32. Engels B, Hanrath M. J. Am. Chem. Soc. 1998; 120: 6356-6361.
33. De Proft F, Schleyer PVR, Van Lenthe JH, Stahl F, Geerlings P. Chem. Eur. J. 2002; 8: 3402-3410.
34. Breton GW, Shugart JH. J. Org. Chem. 2003; 68: 8643-8649.
35. Kwon O, Almond Å, McKee ML. J. Phys. Chem. A 2002; 106: 6864-6870.
36. Özkan I, Kinal A, Balci M. J. Phys. Chem. A 2004; 108: 507-514.
37. Pross A, Glukhovtsev MN, McGrath MP, Radom L. J. Chem. Phys. 1995; 103: 1878-1885.
38. Peng CY, Ayala PY, Schlegel HB, Frisch MJ. J. Comput. Chem. 1996; 17: 49-56.
39. Wiberg KB. Tetrahedron 1968; 24: 1083-1096.
40. Tomasi J, Mennucci B, Cancès E, J. Mol. Struct. (Theochem) 1999; 464: 211-266.
41. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill AW, Johnson BG, Chen W, Wong MW, Andres JL, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.7. Gaussian: Pittsburgh, PA, 1998.
42. Glendening ED, Reed AE, Carpenter JE, Weinhold F. NBO Version 3.1. Theoretical Chemistry Institute, University of Wisconsin, Madison.
43. Huber KP, Herzberg G. Molecular Spectra and Molecular Structure. Constants of Diatomic Molecules, vol. IV. Van Nostrand: New York, 1979.
44. Galli C. J. Org. Chem. 1991; 56: 3238-3245.