DFT investigation of the thermodynamics and mechanism of electrophilic chlorination and iodination of arenes

Journal of Molecular Modeling

Volumn 17, Issue 11, 2011, Pages 2759-2771

  Filimonov, Victor D ^a   Poleshchuk, Oleg Kh ^b   Krasnokutskaya, Elena A ^a   Frenking, Gernot ^c  

^a NATIONAL RESEARCH TOMSK POLYTECHNIC UNIVERSITY   (Russian Federation)

^b TOMSK STATE PEDAGOGICAL UNIVERSITY   (Russian Federation)

^c PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Complex; Complex transition state; Chlorination; DFT; Iodination

Indexed keywords

BENZENE; CHLORINE; IODINE; METHANOL; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; IODINATION; PRIORITY JOURNAL; THERMODYNAMICS;

BENZENE DERIVATIVES; CARBOHYDRATE CONFORMATION; HALOGENATION; MODELS, MOLECULAR; THERMODYNAMICS;

EID: 80255127502     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-011-0964-0     Document Type: Article

References (31)

1. Li JJ, Gribble WG (2000) Palladium in heterocyclic chemistry. A guide for the synthetic chemist. Tetrahedron Org Chem Ser 20:1-413
2. BC Söderberg G Coord 2004 Transition metals in organic synthesis Chem Rev 248 1085 1158
3. Bellina F, Carpita A, Rossi R (2004) Palladium catalysts for the Suzuki cross-coupling reaction: an overview of recent advances. Synthesis 2419-2440 (Pubitemid 39457598)
4. Guiry P, Kiely D (2004) The development of the intramolecular asymmetric Heck reaction. Curr Org Chem 8:781-794 (Pubitemid 38647482)
5. Volkert WA, Hoffman TJ (1999) Therapeutic radiopharmaceuticals. Chem Rev 99:2269-2292
6. Yu SV, Watson AD (1999) Metal-based X-ray contrast media. Chem Rev 99:2353-2377 (Pubitemid 30498115)
7. Filimonov VD, Krasnokutskaya EA, Kh PO, Lesina Yu A (2006) Electronic structures and reactivities of iodinating agents in the gas phase and in solutions: a density functional study. Russ Chem Bull 55:1328-1336
8. Filimonov VD, Krasnokutskaya EA, Kh PO, Lesina Yu A (2008) Theoretical analysis of the reactions of electrophilic iodination and chlorination of benzene and polycyclic arenes in the approximation of density functional theory. Russ J Org Chem 33:681-686
9. PO Kh AG Yureva VD Filimonov G Frenking 2009 Study of a surface of the potential energy for processes of alkanes free-radical iodination by B3LYP/DGDZVP method J Mol Struct THEOCHEM 912 67 72 10.1016/j.theochem.2009.03. 001
10. AD Becke 1993 Density-functional thermochemistry. III. The role of exact exchange J Chem Phys 98 5648 5652 10.1063/1.464913 1:CAS:528:DyaK3sXisVWgtrw%3D
11. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785-789
12. MN Glukhovtsev A Pross MP McGrath L Radom 1995 Extension of Gaussian-2 (G2) theory to bromine- and iodine-containing molecules: use of effective core potentials J Chem Phys 103 1878 1885 10.1063/1.469712 1:CAS:528: DyaK2MXnt1Wjsr0%3D
13. J Tomasi M Perisco 2005 Quantum mechanical continuum solvation models Chem Rev 105 2999 3093 10.1021/cr9904009 1:CAS:528:DC%2BD2MXmsVynurc%3D (Pubitemid 41222791)
14. Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BJ, Robb MA, Cheeseman JR, Keith T, Petersson GA, Montgomery JA, Raghavachari K, Al-Laham MA, Zakrzewski V, Ortiz JV, Foresman JB, Closlowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MB, Andress JL, Replogle ES, Comperts R, Martin RL, Fox DJ, Binkley JS, Defress DJ, Baker J, Stewart JP, Head-Gordon GC, Pople JA (1998) GAUSSIAN 98, revision A. Gaussian Inc., Pittsburgh
15. FW Kirkbride 1956 The heats of chlorination of some hydrocarbons and their chloro-derivatives J Appl Chem 6 11 21 10.1002/jctb.5010060102 1:CAS:528:DyaG1MXmtlai
16. Kovzel EN, Nesterova TN, Rozhnov AM, Kartavzeva TA (1981) Study of equilibrium in in the chlorobenzene-butylchlorobenzenes systems. Thermodyn Org Comp 65-68
17. Butler AR, Sanderson AP (1971) Mechanism of aromatic iodination by iodine and nitric Acid. J Chem Soc B 2264-2268
18. Arotsky J, Mishra HC, Symons MCR (1962) Unstable intermediates. Part XV. Interaction between strong acids and various compounds containing iodine. J Chem Soc 2582-2591
19. Arotsky J, Darby AC, Hamilton JB (1973) Iodination and iodo-compounds. Part IV. The effect of substituents and solvent composition on the rate of aromatic iodination by means of the tri-iodine cation. J Chem Soc Perkin Trans 2:595-599
20. Mulliken RS, Person WB (1969) Molecular complexes. Wiley, New York, p 498
21. 129I in n-sigma and pi-sigma charge-transfer complexes of iodine in the frozen solution. J Chem Phys 72:6192-6198
22. I Drepaul V Fagundez F Guiterrez EH Lau JA Joens 1996 Thermochemistry of molecular complexes of iodine monochloride, iodine monobromide, and bromine with benzene and benzene derivatives J Org Chem 61 3571 3572 10.1021/jo960084n 1:CAS:528:DyaK28XisF2rtLo%3D (Pubitemid 126575809)
23. JT Su AH Zewail 1998 Solvation ultrafast dynamics of reactions. 14. Molecular dynamics and ab initio studies of charge-transfer reactions of iodine in benzene clusters J Phys Chem A 102 4082 4099 10.1021/jp980572u 1:CAS:528:DyaK1cXjtVCns7Y%3D (Pubitemid 128611382)
24. LT Tang Y Wei Y Wang SW Hu XO Liu TW Chu XY Wang 2004 A density functional study on the formation of charge transfer complexes between alkaloids and iodine monochloride J Mol Struct THEOCHEM 686 25 30 10.1016/j.theochem. 2004.07.026 1:CAS:528:DC%2BD2cXptV2rurY%3D
25. SV Rosokha JK Kochi 2002 The preorganization step in organic reaction mechanisms. Charge-transfer complexes as precursors to electrophilic aromatic substitutions J Org Chem 67 1727 1737 10.1021/jo011072r 1:CAS:528: DC%2BD38XhvVanu7s%3D (Pubitemid 34248036)
26. SM Hubig JK Kochi 2000 Structure and dynamics of reactive intermediates in reaction mechanisms. σ- and π-complexes in electrophilic aromatic substitutions J Org Chem 65 6807 6818 10.1021/jo000706b 1:CAS:528: DC%2BD3cXmtlOhtLs%3D
27. Chen R, Cheng YH, Liu L, Li XS, Guo QX (2002) π-Type and σ-type cation-π complexes of atomic cations. Res Chem Intermed 28:41-48 (Pubitemid 34504993)
28. J Chen H Xiao X Gong 2003 DFT study on nitration mechanism of benzene with nitronium ion J Phys Chem A 107 11440 11444 10.1021/jp030167p 1:CAS:528:DC%2BD3sXpt1Wqtb4%3D
29. Sokolov AV (2004) New aspects of electrophylic aromatic substitution mechanism: computational model of nitration reaction. Int J Quant Chem 100:1-12
30. R Ben-Daniel DP de Visser S Shaik R Neumann 2003 Electrophilic aromatic chlorination and haloperoxidation of chloride catalyzed by polyfluorinated alcohols: a new manifestation of template catalysis J Am Chem Soc 125 12116 12117 10.1021/ja0364524 1:CAS:528:DC%2BD3sXnt1Cjt7g%3D (Pubitemid 37238845)
31. Y Wei WB Wang SW Hu TW Chu LT Tang XQ Liu Y Wang XY Wang 2005 Theoretical study of the iodination of methoxybenzene by iodine monochloride J Phys Org Chem 18 625 631 10.1002/poc.911 1:CAS:528:DC%2BD2MXltFyisbw%3D (Pubitemid 40760951)