Insights into the mechanism of the benzoannelated thieno[3,2- b ]furan halogenation. Importance of HOMO-HOMO interaction

Journal of Physical Chemistry A

Volumn 117, Issue 35, 2013, Pages 8449-8458

  Vektariene, Ausra ^a  

^a VILNIUS UNIVERSITY   (Lithuania)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURANS; BOND ORDERING; INTRINSIC REACTION COORDINATE; LONE PAIR ELECTRONS; MINIMAL ENERGY; REACTION COORDINATES; SOLVENT EFFECTS;

AROMATIC COMPOUNDS; ORGANIC POLLUTANTS; SOLVENTS;

HALOGENATION;

BENZOFURAN DERIVATIVE; FURAN DERIVATIVE; THIENO(3,2 B)FURAN; THIENO(3,2-B)FURAN;

ARTICLE; CHEMISTRY; HALOGENATION; THERMODYNAMICS;

BENZOFURANS; FURANS; HALOGENATION; THERMODYNAMICS;

EID: 84883739304     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp402257u     Document Type: Article

References (82)

1. Chacko, E.; Bornstein, J.; Sardella, D. J. Electronic Structure, Aromatic Character, and Chemical Reactivity of o-Quinonoidal Heterocycles J. Am. Chem. Soc. 1977, 99, 8248-8251
2. Abbey, E. R.; Zakharov, L. N.; Liu, Sh.-Y. Electrophilic Aromatic Substitution of a BN Indole J. Am. Chem. Soc. 2010, 132, 16340-16342
3. Hsu, D.-T.; Lin, Ch.-H. Synthesis of Benzo[c] and Naphtho[c]heterocycle Diesters and Dinitriles via Homoelongation J. Org. Chem. 2009, 74, 9180-9187
4. 2-Pyridine Complex and a Preliminary Investigation of the Bound Heterocycle's Reactivity J. Am. Chem. Soc. 2008, 130, 16844-16845
5. Joule, J. A.; Mills, K. Heterocyclic Chemistry; John Wiley & Sons: New York, 2010.
6. Rakowski DuBois, M.; Vasquez, L. D.; Ciancanelli, R. F.; Noll, B. C. Electrophilic Substitution of Nitrogen Heterocycles by Molybdenum Sulfide Complexes Organometallics 2000, 19, 3507-3515
7. Kanney, J.; Noll, B. C.; Rakowski DuBois, M. Reactions of Thiiranes and a Thietane with a High Valent Metal Chloride Organometallics 2000, 19, 4925-4928
8. Liu, F.; Martin-Mingot, A.; Jouannetaud, M.-P.; Zunino, F.; Thibaudeau, S. Superelectrophilic Activation in Superacid HF/SbF5 and Synthesis of Benzofused Sultams Org. Lett. 2010, 12, 868-871
9. Hajós, G.; Riedl, Z.; Kollenz, G. Recent Advances in Ring Transformations of Five-Membered Heterocycles and Their Fused Derivatives Eur. J. Org. Chem. 2001, 18, 3405-3414
10. Hill, R. L.; Kardorff, U.; Rack, M.; Got, N.; Baumann, E.; von Deyn, W.; Engel, S.; Mayer, G.; Otten, M.; Rheinheimer, J.; Witschel, M.; Misslitz, U.; Walter, H.; Westphalen, K. Substituted 4-Benzoylpyrazoles. U.S. Patent 6,028,035, 2000.
11. Janciene, R.; Stumbreviciute, Z.; Vektariene, A.; Sirutkaitis, R.; Podeniene, D.; Palaima, A.; Puodziunaite, B. Interaction of Derivatives of 7-Amino-1,5-benzo-diazepin-2-ones with α,β-Unsaturated Ketones Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 2010, 46, 998-1005
12. Janciene, R.; StumbrevičiuÌ...teÌ, Z.; Vektariene, A.; Kosychova, L.; Klimavičius, A. K.; Palaima, A.; Puodž iuÌ...naiteÌ, B. D. Synthesis of Novel Annelated Systems Based on the Interaction and Reactivity Estimation of Amino-1,5-benzodiazepin-2-ones with Dimethyl-2-oxoglutaconate J. Heterocycl. Chem. 2009, 46, 1339-1345
13. Janciene, R.; StumbrevičiuÌ...teÌ, Z.; Vektariene, A.; Kosychova, L.; Sirutkaitis, R.; Palaima, A.; Puodziunaite, B. Researches on Thiazolo-benzodiazepines. Behavior of Tetrahydro-1,5-benzodiazepinethiones with Aromatic α-Halogen Ketones Hereroat. Chem. 2008, 19, 72-81
14. Cernovska, C.; Kosata, B.; Svoboda, J.; Novotna, V. Novel Ferroelectric Liquid Crystals Based on Fused Thieno[3,2-b]furan and Thieno[3,2-b]thiophene Cores Liq. Cryst. 2006, 33, 987-996
15. Demus, D.; Goodby, J.; Gray, G. W.; Spiess, H.-W.; Vill, V.. Handbook of Liquid Crystals; Wiley-VCH: New York, 1998; Vol. 1.
16. Katritzky, A. R.; Jug, K.; Oniciu, D. C. Quantitative Measures of Aromaticity for Mono-, Bi-, and Tricyclic Penta- and Hexaatomic Heteroaromatic Ring Systems and Their Interrelationships Chem. Rev. 2001, 101, 1421-1449
17. Iskra, J. Halogenated Heterocycles Synthesis, Application and Environment; Springer-Verlag: New York, 2012.
18. Spcranza, M. Gas-Phase Reactivity of Five-Membered Heteroaromatics toward Electrophiles, An Experimental Check on Theoretical Predictions Pure Appl. Chem. 1991, 63, 243-254
19. Seed, A. Synthesis of Self-Organizing Mesogenic Materials Containing a Sulfur-Based Five-Membered Heterocyclic Core Chem. Soc. Rev. 2007, 36, 2046-2069
20. Belenkii, L. I.; Suslov, I. A; Chuvylkin, N. D. Substrate and Positional Selectivity in Electrophilic Substitution Reactions of Pyrrole, Furan, Thiophene and Selenophene Derivatives Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 2003, 39, 36-48
21. Belenkii, L. I.; Kim, T. G.; Suslov, I. A; Chuvylkin, N. D. Substrate and Positional Selectivity in Electrophilic Substitution Reactions in Pyrrole, Furan, Thiophene, And Selenophene Derivatives and Related Benzoannelated Systems Russ. Chem. Bull. 2005, 54, 853-863
22. Domingo, L. R.; Chamorro, E.; Pérez, P. Understanding the Reactivity of Captodative Ethylenes in Polar Cycloaddition Reactions. A Theoretical Study J. Org. Chem. 2008, 73, 4615-4624
23. Jaramillo, P.; Domingo, L. R.; Chamorro, E.; Pérez, P. Mechanistic Details of the Domino Reaction of Nitronaphthalenes with the Electron-Rich Dienes. A DFT Study J. Mol. Struct.: THEOCHEM 2008, 865, 68-72
24. Pérez, P.; Domingo, L. R.; Duque-Noreña, M.; Chamorro, E. A Condensed-to-Atom Nucleophilicity Index. An Application to the Director Effects on the Electrophilic Aromatic Substitutions J. Mol. Struct.: THEOCHEM 2009, 895, 86-91
25. Alves, C. N.; Carneiro, A. S.; Andrés, J.; Domingo, L. R. A DFT study of the Diels-Alder Reaction between Methyl Acrolein Derivatives and Cyclopentadiene. Understanding the Effects of Lewis Acids Catalysts Based on Sulfur Containing Boron Heterocycles Tetrahedron 2006, 62, 5502-5509
26. Ghomri, A.; Mekelleche, S. M. Reactivity and Regioselectivity of Five-Membered Heterocycles in Electrophilic Aromatic Substitution: A Theoretical Investigation J. Mol. Struct.: THEOCHEM 2010, 941, 36-40
27. Mineva, T. T.; Parvanov, V.; Petrov, I.; Neshev, N.; Russo, N. Fukui Indices from Perturbed Kohn-Sham Orbitals and Regional Softness from Mayer Atomic Valences J. Phys. Chem. A 2001, 105, 1959-1967
28. Madjarova, G.; Tadjer, A.; Cholakova, Tz. P.; Dobrev, A. A.; Mineva, T. Selectivity Descriptors for the Michael Addition Reaction as Obtained from Density Functional Based Approaches J. Phys. Chem. A 2005, 109, 387-393
29. Svoboda, J.; Pihera, P.; Sedmera, P.; Palecek, J. Electrophilic Substitution Reactions of [1]Benzothieno[3,2-b]furan Collect. Czech. Chem. Commun. 1996, 61, 888-900
30. Vachal, P.; Pihera, P.; Svoboda, J. Thieno[3,2-b]benzofuran-Synthesis and Reactions Collect. Czech. Chem. Commun. 1997, 62, 1468-1480
31. Vektariene, A.; Vektaris, G.; Svoboda, J. A Theoretical Approach to the Nucleophilic Behavior of Benzofused Thieno[3,2-b]furans Using DFT and HF Based Reactivity Descriptors ARKIVOC (Gainesvill, FL, U. S.) 2009, 7, 311-329
32. Truhlar, D. G.; Garrett, B. C.; Klippenstein, S. J. Current Status of Transition-State Theory J. Phys. Chem. 1996, 100, 12771-12800
33. Fukui, K. Formulation of the Reaction Coordinate J. Phys. Chem. A 1970, 74, 4161-4163
34. Gonzalez, C.; Schlegel, H. B. An Improved Algorithm for Reaction Path Following J. Chem. Phys. 1989, 90, 2154-2161
35. Rauk, A. Orbital Interaction Theory of Organic Chemistry; John Wiley & Sons: New York, 2001.
36. Ogino, T.; Watanabe, T.; Matsuura, M.; Watanabe, Ch.; Ozaki, H. Semiquantitative FMO Analysis of Substituent Effect on the Reaction of Permanganate Ion with Unsymmetrical Alkenes J. Org. Chem. 1998, 63, 2627-2633
37. Spino, C.; Rezaei, H.; Dory, Y. L. Characteristics of the Two Frontier Orbital Interactions in the Diels-Alder Cycloaddition J. Org. Chem. 2004, 69, 757-764
38. Bach, R. D.; Wolber, G. J.; Schlegel, H. B. The Origin of the Barriers to Thermally Allowed, Six-Electron, Pericyclic Reactions: The Effect of HOMO-HOMO Interactions on the Trimerization of Acetylene J. Am. Chem. Soc. 1985, 107, 2837-2841
39. Bach, R. D.; Wolber, G. J. Nucleophilic Substitution at Vinylic Carbon. The Importance of the HOMO-HOMO Interaction J. Am. Chem. Soc. 1984, 106, 1401-1409
40. Bach, R. D.; Wolber, G. J. The Mechanism of Oxygen Transfer from Oxaziridine to Ethylene: The Consequence of HOMO-HOMO Interactions on Frontier Orbital Narrowing J. Am. Chem. Soc. 1984, 106, 1410-1415
41. Bach, R. D.; McDouall, J. J. W.; Schlegel, H. B.; Wolber, G. J. Electronic Factors Influencing the Activation Barrier of the Diels-Alder Reaction. An Ab Initio Study J. Org. Chem. 1989, 54, 2931-2935
42. Bach, R. D.; Coddens, B. A.; McDouall, J. J. W.; Schlegel, H. B.; Davis, F. A.The Mechanism of Oxygen Transfer from an Oxaziridine to a Sulfide and a Sulfoxide: A Theoretical Study J. Org. Chem. 1990, 55, 3325-3330
43. Libit, L.; Hoffmann, R. Detailed Orbital Theory of Substituent Effects. Charge Transfer, Polarization, and the Methyl Group J. Am. Chem. Soc. 1974, 96, 1370-1383
44. Inagaki, S.; Fujimoto, H.; Fukui, K. Orbital Interaction in Three Systems J. Am. Chem. Soc. 1976, 98, 4693-4701
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Gaussian 03, revision C.02; Gaussian Inc.: Wallingford, CT, 2004.
46. Sousa, S. F.; Fernandes, P. A.; Ramos, M. J. General Performance of Density Functionals J. Phys. Chem. A 2007, 111, 10439-10452
47. Morgado, C. A.; McNamara, J. P.; Hillier, I. H.; Burton, N. A.; Vincent, M. A. Density Functional and Semiempirical Molecular Orbital Methods Including Dispersion Corrections for the Accurate Description of Noncovalent Interactions Involving Sulfur-Containing Molecules J. Chem. Theory Comput. 2007, 3, 1656-1664
48. MartInez, A.; Vazquez, M. V.; Carreo-Macedo, J. L.; Sansores, L. E.; Salcedo, R. Benzene Fused Five-Membered Heterocycles. A Theoretical Approach Tetrahedron 2003, 59, 6415-6422
49. Nathaniel, R.; Mineva, T.; Nikolova, R.; Bojilova, A. Density Functional Study of the Interaction of 3-(ω-Bromoacetyl)coumarin with Phosphites Int. J. Quantum Chem. 2006, 106, 1357-1366
50. Vektariene, A.; Vektaris, G. Quantum Chemical Estimation of Reactivity of 2,3,4,5-Tetrahydro-1,5-benzodiazepin-2(1H)-ones in Electrophilic Aromatic Substitution Heteroat. Chem. 2004, 15, 263-270
51. Janciene, R.; Vektariene, A.; Stumbriaviciute, Z.; Kosychova, L.; Klimavicius, A.; Puodziunaite, B. A. Straightforward Synthesis of Novel 4H-Thiazolo[3,2-d][1,5]benzodiazepine Derivatives Heteroat. Chem. 2004, 15, 363-368
52. Vektariene, A.; Vektaris, G.; Rankin, D. W. H. DFT Study of the Regioselectivity of Addition of Sulfenylchloride to Ethenes Heteroat. Chem. 2007, 18, 695-703
53. Janciene, R.; Vektariene, A.; Stumbreviciute, Z.; Puodziunaite, B. D. Experimental and Theoretical Investigation of Substituent Effects in a Two-Pathway Reaction of Tetrahydro-1,5-benzodiazepine-2-thiones with 4-Substituted 2-Bromoacetophenones Monatsh. Chem. 2011, 142, 609-618
54. Choe, S. J. Comparison of Different Theory Models and Basis Sets in Calculations of TPOP24N-Oxide Geometry and Geometries of meso-Tetraphenyl Chlorin N-Oxide Regioisomers Bull. Korean Chem. Soc. 2012, 33, 2861-2866
55. Carlson, H., A.; Nguyen, T. B.; Orozco, M.; Jorgensen, W. L. Accuracy of Free Energies of Hydration for Organic Molecules from 6-31G* Derived Partial Charges J. Comput. Chem. 2004, 14, 1240-1249
56. Rassolov, V. A.; Ratner, M. A.; Pople, J. A.; Redfern, P. C.; Curtiss, L. A. 6-31G* Basis Set for Third-Row Atoms J. Comput. Chem. 2001, 22, 976-984
57. Islam, S. M.; Poirier, R. A. New Insights into the Bromination Reaction for a Series of Alkenes. A Computational Study J. Phys. Chem. A 2007, 111, 13218-13232
58. Islam, S. M.; Huelin, S. D.; Dawe, M.; Poirier, R. A. Comparison of the Standard 6-31G and Binning-Curtiss Basis Sets for Third Row Elements J. Chem. Theory Comput. 2008, 4, 86-100
59. Halgren, T. A.; Lipscomb, W. N. The Synchronous-Transit Method for Determining Reaction Pathways and Locating Molecular Transition States Chem. Phys. Lett. 1977, 49, 225-232
60. Cancès, E.; Mennucci, B.; Tomasi, J. A New Integral Equation Formalism for the Polarizable Continuum Model: Theoretical Background and Applications to Isotropic and Anisotropic Dielectrics J. Chem. Phys. 1997, 107, 3032
61. Mennucci, B.; Cancès, E.; Tomasi, J. Evaluation of Solvent Effects in Isotropic and Anisotropic Dielectrics and in Ionic Solutions with a Unified Integral Equation Method: Theoretical Bases, Computational Implementation, and Numerical Applications J. Phys. Chem. B 1997, 101, 10506-10517
62. Trummal, A.; Rummel, A.; Lippmaa, E.; Burk, P.; Koppel, I. A. IEF-PCM Calculations of Absolute pKa for Substituted Phenols in Dimethyl Sulfoxide and Acetonitrile Solutions J. Phys. Chem. A 2009, 113, 6206-6212
63. Gonzalez, C.; Schlegel, H. B. An Improved Algorithm for Reaction Path Following J. Chem. Phys. 1989, 90, 2154-2161
64. Peterson, T. H.; Carpenter, B. K. Estimation of Dynamic Effects on Product Ratios by Vectorial Decomposition of a Reaction Coordinate. Application to Thermal Nitrogen Loss from Bicyclic Azo Compounds J. Am. Chem. Soc. 1992, 114, 766-767
65. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint Chem. Rev. 1988, 88, 899-926
66. Pierre, H.; Kohn, W. Inhomogeneous Electron Gas Phys. Rev. 1964, 136 (3B) 864-871
67. Kohn, W.; Sham, L. J. Self-Consistent Equations Including Exchange and Correlation Effects Phys. Rev. 1965, 140 (4A) 1133-1138
68. Lide, D. R. Handbook of Chemistry and Physics: A Ready-Reference Book of Chemical and Physical Data; CRC Press: Boca Raton, FL, 2008.
69. Vittadini, A.; Casarin, M.; Selloni, A. Chemistry of and on TiO2 Anatase Surfaces by DFT Calculations: A Partial Review Theor. Chem. Acc. 2007, 117 (5-6) 663-671
70. Bickelhaupt, F. M.; Baerends, E. J. Kohn-Sham Density Functional Theory: Predicting and Understanding Chemistry Rev. Comput. Chem. 2000, 15, 1-86
71. Hoffmann, R. Building Bridges between Inorganic and Organic Chemistry (Nobel Lecture) Angew. Chem., Int. Ed. Engl. 1982, 21, 711-724
72. Hoffmann, R. Solids and Surfaces: A Chemists View of Bonding in Extended Structures; VCH: Weinheim, Germany, 1988.
73. Hoffmann, R.; Woodward, R. B. Conservation of Orbital Symmetry Acc. Chem. Res. 1968, 1, 17-22
74. Fujimoto, H.; Mizutani, Y.; Iwase, K. An Aspect of Substituents and Peripheral Structures in Chemical Reactivities of Molecules J. Phys. Chem. 1986, 90, 2768-277
75. Fujimoto, H. Paired Interacting Orbitals: A Way of Looking at Chemical Interactions Acc. Chem. Res. 1987, 20, 448-453
76. Fujimoto, H.; Satoh, Sh. Orbital Interactions and Chemical Hardness J. Phys. Chem. 1994, 98, 1436-1441
77. Rodrigo, R. S.; Ramalho, T. C.; Santos, J. M.; Figueroa-Villar, J. D. On the Limits of Highest-Occupied Molecular Orbital Driven Reactions: The Frontier Effective-for-Reaction Molecular Orbital Concept J. Phys. Chem. A 2006, 110, 1031-1040
78. Zevallos, J. A.; Toro-Labbé, A. A Theoretical Analysis of the Kohn-Sham and Hartree-Fock Orbitals and Their Use in the Determination of Electronic Properties J. Chil. Chem. Soc. 2003, 48 (4) 39-47
79. Stowasser, R.; Hoffmann, R. What Do the Kohn-Sham Orbitals and Eigenvalues Mean? J. Am. Chem. Soc. 1999, 121, 3414-3420
80. Tee, O. S.; Paventi, M.; Bennett, J. M. Kinetics and Mechanism of the Bromination of Phenols and Phenoxide Ions in Aqueous Solution. Diffusion-Controlled Rates J. Am. Chem. Soc. 1989, 111, 2233-2240
81. Schubert, W. M.; Dial, J. K. Two-Step Mechanism of Noncatalytic Aromatic Bromination. Controlled Variation of the Rate-Controlling Step J. Am. Chem. Soc. 1975, 97, 3877-3878
82. Keefer, R. M.; Andrews, L. J. Halogen Order in the Kinetics of Bromination of Poly(Methylbenzenes) in 90% Aqueous Acetic Acid J. Am. Chem. Soc. 1977, 99, 5693-5695