DFT study on the reactivity of mono-substituted pyridine ligands

Computational and Theoretical Chemistry

Volumn 994, Issue , 2012, Pages 105-111

  Soliman, Saied M ^a  

^a Alexandria University Faculty Of Science   (Egypt)

Author keywords

DFT; Fukui; HSAB; Nucleophilicity; Pyridine

Indexed keywords

EID: 84864753612     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2012.06.020     Document Type: Article

References (78)

1. Kurosaki H., Sharma R.K., Aoki S., Inoue T., Okamoto Y., Sugiura Y., Doi M., Ishida T., Otsuka M., Goto M. Synthesis, characterization, and spectroscopic properties of three novel pentadentate copper(II) complexes related to the metal-chelating inhibitors against DNA binding with HIV-EP1. J. Chem. Soc. Dalton Trans. 2001, 441-447.
2. Sydow G., Wunderlich V., Baumbach L., Tonew E., Tonew M., Schröer H.P. The biological effects of coordination compounds of transitional metals. 6. Effect of 4-methyl-2-aminopyridine-palladium chloride and cis-dichlorodiammine-platinum(II) on retroviruses and the virus-associated RNA polymerase of the influenza virus. Zentralbl. Bakteriol. Mikrobiol. Hyg. 1986, 262:169-178.
3. Hemmert C., Pitie M., Renz M., Gornitzka H., Soulet S., Meunier B. Preparation, characterization and crystal structures of manganese(II), iron(III) and copper(II) complexes of the bis[di-1,1-(2-pyridyl)ethyl]amine (BDPEA) ligand: evaluation of their DNA cleavage activities. J. Biol. Inorg. Chem. 2001, 6:14-22.
4. Kapinos L.E., Sigel H. Acid-base and metal ion binding properties of pyridine-type ligands in aqueous solution. Effect of ortho substituents and interrelation between complex stability and ligand basicity. Inorg. Chim. Acta 2002, 337:131-142.
5. Öĝretir C., Ö zöĝüt D., Yarligan S., Arslan T. Quantum chemical studies on acidity-basicity behaviours of some substituted pyridine derivatives. J. Mol. Struct. (THEOCHEM) 2006, 759:73-78. (and references within).
6. Ziessel R. Schiff-based bipyridine ligands. Unusual coordination features and mesomorphic behaviour. Coord. Chem. Rev. 2001, 216-217:195-223.
7. Hagadorn J.R., Que L., Tolman W.B. N-donor effects on carboxylate binding in mononuclear iron(II) complexes of a sterically hindered benzoate ligand. Inorg. Chem. 2000, 39:6086-6090.
8. Holland J.M., Kilner C.A., Thornton-Pett M., Halcrow M.A. Steric effects on the electronic and molecular structures of nickel(II) and cobalt(II) 2,6-dipyrazol-1-ylpyridine complexes. Polyhedron 2001, 20:2829-2840.
9. Marlin D.S., Olmstead M.M., Mascharak P.K. Structure-spectroscopy correlation in distorted five-coordinate Cu(II) complexes: a case study with a set of closely related copper complexes of pyridine-2,6-dicarboxamide ligands. Inorg. Chem. 2001, 40:7003-7008.
10. Rawat D.S., Benites P.J., Incarvito C.D., Rheingold A.L., Zaleski J.M. The contribution of ligand flexibility to metal center geometry modulated thermal cyclization of conjugated pyridine and quinoline metalloenediynes of copper(I) and copper(II). Inorg. Chem. 2001, 40:1846-1857.
11. Lipinski R., Chruscinski L., Mlynarz P., Boduszek B., Kozlowski H. Coordination abilities of amino-phosphonate derivatives of pyridine. Inorg. Chim. Acta 2001, 322:157-161.
12. Chruscinski L., Mlynarz P., Malinowska K., Ochocki J., Boduszek B., Kozlowski H. Methylphosphonate, hydroxymethylphosphonate and aminomethylphosphonate ligands containing pyridine, pyrazole or imidazole side chains: the coordination abilities towards Cu(II) ions. Inorg. Chim. Acta 2000, 303:47-53.
13. Basolo F., Pearson R.G. Mechanism of Inorganic Reactions 1967, Wiley, New York. second ed.
14. Parr R.G., Pearson R.G. Absolute hardness: companion parameter to absolute electronegativity. J. Am. Chem. Soc. 1983, 105:7512-7516.
15. Pearson R.G. Absolute electronegativity and hardness: application to inorganic chemistry. Inorg. Chem. 1988, 27:734-740.
16. Pearson R.G. Chemical hardness and bond dissociation energies. J. Am. Chem. Soc. 1988, 110:7684-7690.
17. Pearson R.G. Absolute electronegativity and hardness: applications to organic chemistry. J. Org. Chem. 1989, 54:1423-1430.
18. Pearson R.G. The HSAB principle - more quantitative aspects. Inorg. Chim. Acta 1995, 240:93-98.
19. Deng H., Kebarle P. Bond energies of copper ion-ligand L complexes CuL2+ determined in the gas phase by ion-ligand exchange equilibria measurements. J. Am. Chem. Soc. 1998, 120:2925-2931.
20. Méndez F., Romero M.D.-L., Proft F.D., Geerlings P. The basicity of p-substituted phenolates and the elimination-substitution ratio in p-nitrophenethyl bromide: a HSAB theoretical study. J. Org. Chem. 1998, 63:5774-5778.
21. Datta D., Singh S.N. Pearson's chemical hardness, heterolytic dissociative version of Pauling's bond-energy equation and a novel approach towards understanding Pearson's hard-soft acid-base principle. J. Chem. Soc. Dalton Trans. 1991, 1541-1549.
22. Chattaraj P.K., Schleyer P.V.R. An ab initio study resulting in a greater understanding of the HSAB principle. J. Am. Chem. Soc. 1994, 116:1067-1071.
23. Méndez F., Tamariz J., Geerlings P. 1,3-Dipolar cycloaddition reactions: a DFT and HSAB principle theoretical model. J. Phys. Chem. A 1998, 102:6292-6296.
24. Pérez P., Toro-Labbé A., Contreras R. HSAB analysis of charge transfer in the gas-phase acid-base equilibria of alkyl-substituted alcohols. J. Phys. Chem. A 1999, 103:11246-11249.
25. -. Organometallics 1998, 17:4326-4328.
26. Nalewajaki R.F. Electrostatic effects in interactions between hard (soft) acids and bases. J. Am. Chem. Soc. 1984, 106:944-945.
27. Chattaraj P.K., Lee H., Parr R.G. Principle of maximum hardness. J. Am. Chem. Soc. 1991, 113:1854-1855.
28. Ramos-Morales F.R., Niconoff S.D., Basurto J.C., Bustamante F.J., Sánchez J.S. Theoretical study of reactivity based on the hard-soft/acid-base (HSAB) in isatoic anhydride and some derivatives. J. Mex. Chem. Soc. 2008, 52(4):241-248.
29. Campodónico P.R., Aizman A., Contreras R. Empirical scale of nucleophilicity for substituted pyridines. Chem. Phys. Lett. 2006, 422:204-209.
30. Shoeib T., Gorelsky S.I., Lever A.B.P., Siu K.W.M., Hopkinson A.C. Note when does the hard and soft acid base principle apply in the gas phase?. Inorg. Chim. Acta 2001, 315:236-239.
31. Shoeib T., El Aribi H., Michael Siu K.W., Hopkinson Alan C. A study of silver (I) ion-organonitrile complexes: ion structures, binding energies, and substituent effects. J. Phys. Chem. A 2001, 105(4):710-719.
32. Woodward S. HSAB matching and dismatching in selective catalysis and synthesis. Tetrahedron 2002, 58:1017-1050.
33. Tuszkanow M., Daszkiewicz M., Maciejewska G., Staszak Z., Wietrzyk J., Filip B., Golonka M. HSAB principle and nickel(II) ion reactivity towards 1-methyhydantoin. Polyhedron 2011, 30:2016-2025.
34. Yan M.K., Zheng C., Yin J., An Z.F., Chen R.F., Feng X.M., Fan J.S.Q., Huang W. Theoretical study of organic molecules containing N or S atoms as receptors for Hg(II) fluorescent sensors. Synth. Met. 2012, 162:641-649.
35. Geerlings P., De Proft F., Langenaeker W. Conceptual density functional theory. Chem. Rev. 2003, 103:1793-1873.
36. Chattaraj P.K., Sarkar U., Roy D.R. Electrophilicity index. Chem. Rev. 2006, 106:2065-2091.
37. Chattaraj P.K., Maiti B., Sarkar U. Philicity: a unified treatment of chemical reactivity and selectivity. J. Phys. Chem. A 2003, 107:4973-4975.
38. Roy D.R., Parthasarathi R., Padmanabhan J., Sarkar U., Subramanium V., Chattaraj P.K. Careful scrutiny of the philicity concept. J. Phys. Chem. A 2006, 110:1084-1093.
39. Padmanabhan J., Parthasarathi R., Elango M., Subramanian V., Krishnamoorthy B.S., Gutierrez-Oliva S., Toro-Labbé A., Roy D.R., Chattaraj P.K. A multiphilic descriptor for chemical reactivity and selectivity. J. Phys. Chem. A 2007, 111:9130-9138.
40. Jaramillo P., Pérez P., Contreras R., Tiznado W., Fuentealba P. On the definition of a nucleophilicity scale. J. Phys. Chem. A 2006, 110:8181-8187.
41. Jaramillo P., Domingo L.R., Chamorro E., Perez P. A further exploration of a nucleophilicity index based on the gas phase ionization potentials. J. Mol. Struct. (THEOCHEM) 2008, 865:68-72.
42. Perez P., Domingo L.R., Doque-Norena 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.
43. Gazquez J.L., Cedillo A., Vela A. Electrodonating and electroaccepting powers. J. Phys. Chem. A 2007, 111:1966-1970.
44. Pratihar S., Roy S. Nucleophilicity and site selectivity of commonly used arenes and heteroarenes. J. Org. Chem. 2010, 75:4957-4963.
45. Deuri S., Phukan P. A DFT study on nucleophilicity and site selectivity of nitrogen nucleophiles. Comput. Theor. Chem. 2012, 980:49-55.
46. Martin R.B. Nucleoside sites for transition metal ion binding. Acc. Chem. Res. 1985, 18:32-38.
47. Sigel H., Corfu N.A., Ji L.-n., Martin R.B. On the dichotomy of metal ion binding in adenosine complexes, comments. Inorg. Chem. 1992, 13:35-59.
48. Kinjo Y., Tribolet R., Corfu N.A., Sigel H. Stability and structure of xanthosine-metal ion complexes in aqueous solution, together with intramolecular adenosine-metal ion equilibria. Inorg. Chem. 1989, 28:1480-1489.
49. Kahmann K., Sigel H., Erlenmeyer H. Sulfur atom in aromatic compounds as ligand in chelate complex. Helv. Chim. Acta 1964, 47:1754-1763.
50. Sun M.S., Brewer D.G. Comparative formation constants for complexes of copper, nickel, and silver with some substituted pyridines. Can. J. Chem. 1967, 45:2729-2739.
51. Sigel H., Wynberg H., van Bergen T.J., Kahmann K. Acidity constants of the thienyl- and phenyl-pyridines and stability constants of the corresponding copper (II) 1:1 complexes. Helv. Chim. Acta 1972, 55:610-613.
52. Arpalahti J., Lönnberg H. Complexing of 3d transition metal ions with 9-substituted purines. I. Binding sites in aqueous solution. Inorg. Chim. Acta 1983, 78:63-68.
53. Kim S.-H., Martin R.B. Binding sites and stabilities of transition metal ions with nucleosides and related ligands. Inorg. Chim. Acta 1984, 91:19-24.
54. Ji L.-n., Corfu N.A., Sigel H. Stability of some metal-ion complexes of tubercidin (=7-deazaadenosine) in aqueous solution. An o-amino group inhibits complexation at N1 of purines. J. Chem. Soc., Dalton Trans. 1991, 1367-1375.
55. M.J. Frisch, et al., Gaussian-03, Revision C.01, Gaussian, Inc., Wallingford, CT, 2004.
56. Parr R.G., Donnelly R.A., Levy M., Palke W.E. Electronegativity: the density functional viewpoint. J. Chem. Phys. 1978, 68:3801-3808.
57. Parr R.G., Szentpaty L.V., Liu S. Electrophilicity index. J. Am. Chem. Soc. 1999, 121:1922-1924.
58. Yang W., Mortier W.J. The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines. J. Am. Chem. Soc. 1986, 108:5708-5711.
59. Reed A.E., Curtiss L.A., Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88:899-926.
60. Özcan M., Dehri I., Erbil M. Organic sulphur-containing compounds as corrosion inhibitors for mild steel in acidic media: correlation between inhibition efficiency and chemical structure. Appl. Surf. Sci. 2004, 236:155-164.
61. Pearson R.G. Hard and soft acids and bases. J. Am. Chem. Soc. 1963, 85:3533-3543.
62. Klopman G., Hudson R.F. Polyelectronic perturbation treatment of chemical reactivity. Theor. Chem. Acta 1967, 8:165-174.
63. Klopman G. Chemical reactivity and the concept of charge- and frontier-controlled reactions. J. Am. Chem. Soc. 1968, 90:223-234.
64. Pilepicć V., Uršić S. Nucleophilic reactivity of the nitroso group. Fukui function DFT calculations for nitrosobenzene and 2-methyl-2-nitrosopropane. J. Mol. Struct. (THEOCHEM) 2001, 538:41-49. (and reference within).
65. Chattaraj P.K., Maiti B. Reactivity dynamics in atom-field interactions: a quantum fluid density functional study. J. Phys. Chem. A 2001, 105:169-183.
66. Chermette H. Chemical reactivity indexes in density functional theory. J. Comput. Chem. 1999, 20:129-154.
67. Roy R.K., De Proft F., Geerlings P. Site of protonation in aniline and substituted anilines in the gas phase: a study via the local hard and soft acids and bases concept. J. Phys. Chem. A 1998, 102:7035-7040.
68. Langenaeker W., De Proft F., Geerlings P. Electron correlation effects on Fukui functions. J. Mol. Struct. (THEOCHEM) 1996, 362:175-179.
69. Arulmozhiraja S., Kolandaivel P. Condensed Fukui function: dependency on atomic charges. Mol. Phys. 1997, 90:55-62.
70. Langenaeker W., De Decker M., Geerlings P. Quantum-chemical study of the Fukui function as a reactivity index: probing the acidity of bridging hydroxyls in zeolite-type model systems. J. Mol. Struct. (THEOCHEM) 1990, 207:115-130.
71. Gazquez J.L., Galvan A., Vela Chemical reactivity in density functional theory: the N-differentiability problem. J. Mol. Struct. (THEOCHEM) 1990, 210:29-38.
72. Li Y., Evans J.N.S. The Fukui function: a key concept linking frontier molecular orbital theory and the hard-soft-acid-base principle. J. Am. Chem. Soc. 1995, 117:7756-7759.
73. Chandra A.K., Michalak A., Nguyen M.T., Nalewajski R.F. Regional matching of atomic softnesses in chemical reactions: a two-reactant charge sensitivity study. J. Phys. Chem. 1998, 102:10182-10188.
74. Gaâzquez J.L., Meândez F. The hard and soft acids and bases principle: an atoms in molecules viewpoint. J. Phys. Chem. 1994, 98:4591-4593.
75. Krishnamurti S., Roy R.K., Vetrivel R., Iwata S., Pal S. The local hard-soft acid-base principle: a critical study. J. Phys. Chem. A 1997, 101:7253-7257.
76. 2CO. J. Mol. Struct. (THEOCHEM) 1988, 163:305-313.
77. Katritzky A.R., Pozharski A.F. Handbook of Heterocyclic Chemistry 2000, Elsevier, Pergamon. second ed.
78. NIST/EPA. http://webbook.nist.gov/chemistry.