Relation between the substituent effect and aromaticity in imidazole derivatives: A comparative study

Computational and Theoretical Chemistry

Volumn 994, Issue , 2012, Pages 97-104

  Chermahini, Alireza Najafi ^a   Hosseinzadeh, Behzad ^b   Beni, Alireza Salimi ^b   Teimouri, Abbas ^c  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

^b YASOUJ UNIVERSITY   (Iran)

^c PAYAME NOOR UNIVERSITY   (Iran)

Author keywords

HOMA; Imidazolate; Imidazole; NBO; NICS; Protonated imidazole

Indexed keywords

EID: 84864291509     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2012.06.024     Document Type: Article

References (60)

1. Katritzky A.R., Barczynski P., Musumarra G., Pisano D., Szafran M. Aromaticity as a quantitative concept. 1. A statistical demonstration of the orthogonality of classical and magnetic aromaticity in five- and six-membered heterocycles. J. Am. Chem. Soc. 1989, 111:7-15.
2. Minkin V.I., Glukhovtsev M.N., Simkin B.Y. Aromaticity, Antiaromaticity 1994, John Wiley & Sons, New York, pp.313.
3. Schleyer P.V.R., Jiao H. What is aromaticity?. Pure Appl. Chem. 1996, 68:209-218.
4. Lloyd D. What is aromaticity?. J. Chem. Inf. Comput. Sci. 1996, 36:442-447.
5. Krygowski T.M., Cyrański M.K., Czarnocki Z., Hafelinger G., Katritzky A.R. Aromaticity: a theoretical concept of immense practical importance. Tetrahedron 2000, 56:1783-1796.
6. Garrat P.J. Aromaticity 1986, Wiley, New York.
7. (Special Issue on Aromaticity). Chem. Rev. 2005, 105:3842-3888.
8. Cyrański M.K., Krygowski T.M., Katritzky A.R., Schleyer P.v.R. To what extent can aromaticity be defined uniquely?. J. Org. Chem. 2002, 67:1333-1338.
9. Stanger A. What is... aromaticity: a critique of the concept of aromaticity-can it really be defined?. Chem. Commun. 2009, 15:1939-1947.
10. Kekulé A. Sur la constitution des substances aromatiques. Bull. Soc. Chim. Fr. 1865, 3:98-110.
11. Schleyer P.V.R. Introduction: aromaticity. Chem. Rev. 2001, 101:1115-1118.
12. Krygowski T.M. Crystallographic studies of inter- and intramolecular interactions reflected in aromatic character of p-electron systems. J. Chem. Inf. Comput. Sci. 1993, 33:70-78.
13. Krygowski T.M., Cyrański M.K. Separation of the energetic and geometric contributions to the aromaticity of p-electron carbocyclics. Tetrahedron 1996, 52:1713-1722.
14. T.M. Krygowski, M.K. Cyrański, Aromatic character of carbocyclic p-electron systems deduced from molecular geometry, in: M. Hargittai, I. Hargittai (Eds.), Advances in Molecular Structure Research, London, 1997, pp. 227-268.
15. Krygowski T.M., Cyrański M.K. Structural aspects of aromaticity. Chem. Rev. 2001, 101:1385-1419.
16. Schleyer P.v.R., Maerker C., Dransfeld A., Jiao H., van Eikema Hommes N.J.R. Nucleus-independent chemical shifts: a simple and efficient aromaticity probe. J. Am. Chem. Soc. 1996, 118:6317-6318.
17. Chen Z., Wannere C.S., Corminboeuf C., Puchta R., Schleyer P.v.R. Nucleus-independent chemical shifts (NICS) as an aromaticity criterion. Chem. Rev. 2005, 105:3842-3888.
18. Schleyer P.v.R., Manoharan M., Wang Z.-X., Kiran B., Jiao H., Puchta R., vanEikema Hommes N.J.R. Dissected nucleus-independent chemical shift analysis of π-aromaticity and antiaromaticity. Org. Lett. 2001, 3:2465-2468.
19. Schleyer P.v.R., Jiao H., van Eikema Hommes N.J.R., Malkin V.G., Malkina O. An evaluation of the aromaticity of inorganic rings: refined evidence from magnetic properties. J. Am. Chem. Soc. 1997, 119:12669-12670.
20. Oziminski W.P., Dobrowolski J.C. Σ and π electron contributions to the substituent effect: natural population analysis. J. Phys. Org. Chem. 2009, 22:769-778.
21. Mazurek A., Dobrowolski J.C. Heteroatom incorporation effect in σ- and π-electron systems: the sEDA(II) and pEDA(II) descriptors. J. Org. Chem. 2012, 77:2608-2618.
22. Krygowski T.M., Oziminski W.P., Ramsden C.A. Sigma- and pi- electron structure of aza-azoles. J. Mol. Model. 2011, 17:1427-1433.
23. Oziminski W.P., Krygowski T. Comparison of the substituent effects in tetrazole systems and benzene. A computational study. Tetrahedron 2011, 6(7):6316.
24. Lambardino J.G., Wiseman E.H. Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles. J. Med. Chem. 1974, 17:1182-1188.
25. Golan D.E., Armstrong A.W. Principles of pharmacology: the pathophysiologic basis of drug therapy. Wolters Kluwer Health 2007, 107:88-99.
26. Bhat N.R., Zhang P.S., Mohanty S.B. p38 MAP kinase regulation of oligodendrocyte differentiation with CREB as a potential target. Neurochem. Res. 2007, 32:293-302.
27. Faulkner D.J. Marine natural products. Nat. Prod. Rep. 2000, 17:7-55.
28. Ho J.Z., Hohareb R.M., Ahn J.H., Sim T.B., Rapoport H.J. Enantiospecific synthesis of arbapentostatins. Org. Chem. 2003, 68:109-114.
29. Grimmett M.R. Comprehensive Heterocyclic Chemistry II 1996, 77-220. Pergamon, Oxford. A.R. Katritsky, E.F.V. Scriven (Eds.).
30. Grimmett M.R. Advances in imidazole chemistry. Adv. Heterocycl. Chem. 1970, 12:103-183.
31. Novelli A., De Santis A. General synthesis of C substituted imidazoles. Tetrahedron Lett. 1967, 8:265-269.
32. Grimmett M.R. Imidazole and Benzimidazole Synthesis 1997, Academic Press, New York.
33. Laufer S., Wagner G., Kotschenreuther D. Ones, thiones, and N-oxides: An exercise in imidazole chemistry. Angew. Chem. Int. Ed. 2002, 41:2290-2293.
34. Lai C.-L., Lee H.M., Hu C.-H. Theoretical study on the mechanism of N-heterocyclic carbene catalyzed transesterification reactions. Tetrahedron Lett. 2005, 46:6265-6270.
35. Perry M.C., Burgess K. Chiral N-heterocyclic carbene-transition metal complexes in asymmetric catalysis. Tetrahedron Asymmetry 2003, 14:951-961.
36. Dupont J., de Souza R., Suarez P. Ionic liquid (molten salt) phase organometallic catalysis. Chem. Rev. 2002, 102:3667-3692.
37. Kubicki M. Two tautomers in one crystal: 4 (5)-nitro-5 (4)-methoxyimidazole. Acta Crystallogr. Sect. B 2004, 60:191-196.
38. Maeki J., Taehtinen P., Kronberg L., Klika K.D. Restricted rotation/tautomeric equilibrium and determination of the site and extent of protonation in bi-imidazole nucleosides by multinuclear NMR and GIAO-DFT calculations. J. Phys. Org. Chem. 2005, 18:240-249.
39. Sadlej J., Jaworski A., Miaskiewicz K. A theoretical study of the vibrational spectra of imidazole and its different forms. J. Mol. Struct. 1992, 274:247-257.
40. Li G.-S., Ruiz-Lopez M.F., Zhang M.-S., Maigret B. Ab initio calculations of tautomer equilibrium and protonation enthalpy of 4-and 5-methylimidazole in the gas phase: basis set and correlation effects. J. Mol. Struct. (Theochem.) 1998, 422:197-204.
41. Cho S.-G., Cheun Y.-G., Park B.-S. A computational study of imidazole, 4-nitroimidazole, 5-nitroimidazole and 4, 5-dinitroimidazole. J. Mol. Struct. (Theochem.) 1998, 432:41-53.
42. Raczynaska E.D. Application of semiempirical method (AM1) to the study of tautomeric equilibria in the gas phase for simple compounds containing the amidine group: 4(5)-substituted imidazoles. Anal. Chim. Acta 1997, 348:431-441.
43. Worth G.A., King P.M., Richards W.G. Theoretical calculation of tautomer equilibria in solution: 4-(5-)methylimidazole. Biochem. Biophys. Acta 1989, 993:134-136.
44. Li G.-S., Ruiz-Lopez M.F., Zhang M.-S., Maigret B. Isolation of smaller nanocrystal au molecules: robust quantum effects in optical spectra. J. Phys. Chem. 1997, 101:7885-7891.
45. Luque F.J., Lopez-Bes J.M., Cemeli J., Aroztegui M., Orozco M. Solvent effects on tautomerism equilibria in heterocycles. Theor. Chem. Acc. 1997, 96:105-113.
46. Cysewski P. An ab initio study on nucleic acid bases aromaticities. J. Mol. Struct. (Theochem.) 2005, 714:29-34.
47. Mrozek A., Karolak-Wojciechowskaa J., Kiec-Kononowicz K. Five-membered heterocycles. Part III. Aromaticity of 1,3-imidazole in 5+n hetero-bicyclic molecules. J. Mol. Struct. (Theochem) 2003, 655:397-403.
48. Pozharsky A.F. Heteroaromaticity (review). Chem. Heterocycl. Compd. 1985, 21:717-749.
49. Krygowski T.M. Crystallographic studies of inter- and intramolecular interactions reflected in aromatic character of pi-electron systems. J. Chem. Inf. Comput. Sci. 1993, 33:70-78.
50. Krygowski T.M., Cyranski M.K. Separation of the energetic and geometric contributions to the aromaticity. Part IV. A general model for the π-electron systems. Tetrahedron 1996, 52:10255-10264.
51. Schleyer P.V.R., Maerker C., Dransfeld A., Jiao H., Hommes N.J.R.V.E. Magnetic evidence for the aromaticity and antiaromaticity of charged fluorenyl, indenyl, and cyclopentadienyl systems. J. Am. Chem. Soc. 1997, 119:7075-7083.
52. Subramanian G., Schleyer P.V.R., Jiao H. Aromaticity of annelated borepins. Organometallics 1997, 16:2362-2369.
53. Chermahini A.N., Dabbagh H.A., Teimouri A. Relation between the substituent effect and aromaticity in tetrazoles, protonated tetrazoles and tetrazolate derivatives. J. Mol. Struct. (Theochem) 2007, 822:33-37.
54. Chermahini A.N., Dabbagh H.A., Teimouri A. Theoretical studies on tautomerism of dihydropyrimidine tautomers. J. Mol. Struct. (Theochem) 2008, 857:105-110.
55. Chermahini A.N., Ghaedi A., Teimouri A., Momenbeik F., Dabbagh H.A. Density functional theory study of intermolecular interactions of cyclic tetrazole dimers. J. Mol. Struct. (Theochem) 2008, 867:78-84.
56. M.J. Frisch et al., Gaussian 03, Pittsburgh, PA, 2003.
57. Wolinski K., Hilton J.F., Pulay P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc. 1990, 112:8251-8260.
58. Gordy W.J. Dependence of bond order and of bond energy upon bond length. Chem. Phys. 1947, 15:305-310.
59. E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold. NBO Version 3.1.
60. Roman M., Dobrowolski J.Cz., Baranska M. Theoretical modeling of molecular spectra parameters of disubstituted diacetylenes. J. Chem. Inf. Model. 2011, 51:283-295.