Theoretical study of changes in π-electron delocalization in the analogues of an ortho-Hydroxy schiff base when the proton is replaced with Li+ or BeH+

Journal of Chemical Information and Modeling

Volumn 45, Issue 6, 2005, Pages 1837-1841

  Krygowski, Tadeusz M ^a   Zachara, Joanna E ^a   Moszyński, Robert ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BERYLLIUM COMPOUNDS; DERIVATIVES; ISOMERS; MOLECULAR GRAPHICS; OPTIMIZATION; PROTONS;

AROMATICITY; ELECTRON DELOCALIZATION; TAUTOMER;

ELECTRONIC STRUCTURE;

EID: 28944446564     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci0502911     Document Type: Conference Paper

References (54)

1. (a) Ferretti, V.; Gilli, P.; Bertolesi V.; Gilli, G. Structure Correlation Methods in Chemical Crystallography. Cryst. Rev. 1996, 5, 3-104.
2. (b) Grabowski, S. J. Hydrogen Bonding Strength - Measures Based on Geometric and Topological Parameters. J. Phys. Org. Chem. 2004, 17, 18-31.
3. Gilli, G.; Belluci, F.; Ferretti, V.; Bertolesi, V. Evidence for Resonance Assisted Hydrogen Bonding from Crystal Structure Correlations on the Enol Form of the β-Diketone Fragment. J. Am. Chem. Soc. 1989, 111, 1023-1028.
4. Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. Evidence for Resonance Assisted Hydrogen Bonding. 2. Intercorrelation between Crystal Structure and Spectroscopic Parameters in Eight Intramolecularly Hydrogen Bonded 1,3-Diaryl-1,3-propanedione Enols. J. Am. Chem. Soc. 1991, 113, 4917-4925.
5. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. Covalent Nature of the Strong Homonuclear Hydrogen Bond. Study of the O-H...O System by Crystal Structure Correlation Methods. J. Am. Chem. Soc. 1994, 116, 909-915.
6. Gilli, P.; Bertolasi, V.; Pretto, L.; Ferretti, V.; Gilli, G. Covalent versus Electrostatic Nature of the Strong Hydrogen Bond: Discrimination among Single, Double and Asymmetric Single-Well Hydrogen Bonds by Variable-temperature X-ray Crystallographic Methods in β-Diketone Enol RAHB Systems. J. Am. Chem. Soc. 2004, 126, 3845-3855.
7. Grabowski, S. J. π-Electron Delocalization for Intramolecular Resonance Assisted Hydrogen Bonds. J. Phys. Org. Chem. 2003, 16, 797-802.
8. (b) Grabowski, S. J. Properties of a Ring Critical Point as Measures of Intramolecular H-Bond Strength. Monatsh. Chem. 2002, 133, 1373-1380.
9. (c) Grabowski, S. J. An Estimation of Strength of Intramolecular Hydrogen Bonds - Ab Initio and AIM Studies, J. Mol. Struct. 2001, 562, 137-143.
10. Steiner, T. The Hydrogen Bond in the Solid State. Angew. Chem., Int. Ed. 2002, 41, 48-76.
11. Kruszewski, J.; Krygowski, T. M. Definition of Aromaticity Basing on the Harmonic Oscillator Model. Tetrahedron Lett. 1972, 36, 3839-3842.
12. Krygowski, T. M. Crystallographic Studies of Intra- and Intermolecular Interactions Reflected in Aromatic Character of π-Electron Systems. J. Chem. Inf. Comput. Sci. 1993, 33, 70-78.
13. Krygowski, T. M.; Cyrański, M. K. Structural Aspects of Aromaticity. Chem. Rev. 2001, 101, 1385-1419.
14. (a) Castro, C.; Chen, Z.; Wannere, C. S.; Jiao, H.; Karney, W. L.; Mauksch, M.; Puchta, R.; Hommes, N. J. R. v. E.; Schleyer, P. v. R. Investigation of a Putative Möbius Aromatic Hydrocarbon. The Effect of Benzannelation on Möbius [4n]Annulene Aromaticity. J. Am. Chem. Soc. 2005, 127, 2425-2432.
15. (b) Poater, J.; Garcia-Cruz, I.; Illas, F.; Solà, M. Discrepancy Between Common Local Aromaticity Measures in a Series of Carbazole Derivatives. Phys. Chem. Chem. Phys. 2004, 6, 314-318.
16. (c) Krygowski, T. M.; Zachara, J. E.; Szatyłowicz, H. Molecular Geometry as a Source of Chemical Information. 3. How H-Bonding Affects Aromaticity of the Ring in the Case of Phenol and p-Nitrophenol Complexes: A B3LYP/6-311+G** Study. J. Org. Chem. 2004, 69, 7038-7043.
17. + in Variously Substituted Malonaldehydes. Theor. Chem. Acc. 2005, in press.
18. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. Evidence for Intramolecular N-H...O Resonance Assisted Hydrogen Bonding in β-Enaminoness and Related Heterodienes. A Combined Crystal Structural, IR and NMR Spectroscopic, and Quantum Mechanical Investigations. J. Am. Chem. Soc. 2000, 122, 10405-10417.
19. Vigato, P. A.; Tamburini, S. The Challenge of Cyclic and Acyclic Schiff Bases and Related Derivatives. Coord. Chem. Rev. 2004, 248, 1717-2128.
20. (a) Dziembowska, T. Intramolecular Hydrogen Bonding. Pol. J. Chem. 1994, 69, 1455-1489.
21. (b) Dziembowska, T. Resonance Assisted Intramolecular Hydrogen Bond in Schiff Bases. Pol J. Chem. 1998, 72, 193-209.
22. Suresh, C. H.; Koga, N. A Molecular Electrostatic Potential Bond Critical Point Model and Group Electronegativities. J. Am. Chem. Soc. 2002, 124, 1790-1797.
23. Krygowski, T. M.; Woźniak, K.; Anulewicz, R.; Pawlak, D.; Kołodziejski, W.; Grech, E.; Szady, A. Through-Resonance Assisted Ionic Hydrogen Bonding in 5-Nitro-N-salicylideneethylamine. J. Phys. Chem. A 1997, 101, 9399-9404.
24. Dominiak, P.; Grech, E.; Barr, G.; Teat, S.; Mallison, P.; Woźniak K. Neutral and Ionic Hydrogen Bonding in Schiff Bases. Chem. Eur. J. 2003, 9, 963-970.
25. (a) Coppens, P.; Schmidt, G. M. J. The Crystal Structure of the a-Modification of p-Nitrophenol near 90K. Acta Crystallogr. 1965, 18, 62-67.
26. (b) Coppens, P.; Schmidt, G. M. J. The Crystal Structure of the Metastable (β) Modification of p-Nitrophenol. Acta Crystallogr. 1965, 18, 654-663.
27. Krygowski, T. M.; Stepień, B.; Anulewicz-Ostrowska, R.; Dziembowska, T. π-Electron Delocalization in the Spacer of the O-H...N Bridge in Schiff Bases. Crystal and Molecular Structure of 3,5-dimethoxy- 2[(phenyimino)methyl]phenol and 4-methoxy-[(phenylimino)methyl]phenol. Tetrahedron 1999, 55, 5457-5464.
28. Krygowski, T. M.; Stepień, B. T.; Anulewicz-Ostrowska, R.; Cyrański, M. K.; Grabowski, S. J.; Rozwadowski, Z.; Dziembowska, T. Crystal and Molecular Structure of N-(3,5-dichloro-2-hydroxybenzylidene) and N-(2-hydroxy-3-methoxy-benzylidene)aniline oxides. Delocalization in the Spacer of the Intramolecular H-Bond and the Problem of Quasi-Aromaticity. Collect. Czech. Chem. Commun. 1999, 64, 1797-1806.
29. Filarowski, A. Intramolecular Hydrogen Bonding in o-Hydroxyaryl Schiff Bases. J. Phys. Org. Chem. 2005, 18, 686-698.
30. (a) Scheiner, S. In Hydrogen Bonding. A Theoretical Perspective; Oxford University Press: Oxford, 1997.
31. (b) Szalewicz, K. Hydrogen Bond in Encyclopedia of Physical Science and Technology, 3rd ed.; Academic Press: New York, 2002; Vol. 7, pp 505-538.
32. (c) Buckingham, A. D. In The Hydrogen Bond: An Electrostatic Interaction? Theoretical Treatments of Hydrogen Bonding; Hadži, D., Ed.; John Wiley & Sons Ltd.: Chichester, 1997.
33. (a) Sannigrahi, A. B.; Kar, T.; Niyogi, B. G.; Hobza, P.; Schleyer P. v. R. The Lithium Bond Reexamined. Chem. Rev. 1990, 90, 1061-1076.
34. - (X = F, Cl, and Br) Complexes: Topological Analysis of Electron Localization Function. Int. J. Quantum Chem. 2002, 90, 1108-1120.
35. Reihlen, H.; Illig, R.; Wittig, R. On the Reactivity of Coordinated Organic Compounds. Chem. Ber. 1925, 58, 12-19.
36. Calvin, M.; Wilson, K. W. Stability of Chelate Compounds. J. Am. Chem. Soc. 1945, 67, 2003-2007.
37. Djordjevic, C.; Lewis, J.; Nyholm, R. S. Reactivity of Coordinated Acetylacetone. Chem. Ind. (London) 1959, 122-123.
38. Collman, J. P.; Moss, R. A.; Maltz, H.; Heindel, C. C. The Reaction of Metal Chelates. I. Halogenation of Metal Chelates of 1,3-Diketones. J. Am. Chem. Soc. 1961, 83, 531-534.
39. Perrin, C. L.; Kim, Y. J. Symmetry of Metal Chelates. Inorg. Chem. 2000, 39, 3902-3910.
40. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T., Jr.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
41. zz value, the more aromatic is the ring.
42. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. Nucleus Independent Chemical Shift - A Simple and Efficient Aromaticity Probe. J. Am. Chem. Soc. 1996, 118, 6317-6318.
43. Schleyer, P. v. R.; Manoharan, M.; Wang, Z.-X.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. J. R. v. E. Dissected Nucleus-Independent Chemical Shift Analysis of π-Aromaticity and Antiaromaticity Org. Lett. 2001, 3, 2465-2468.
44. Corminboeuf, C.; Heine, T.; Seifert, G.; Schleyer, P. v. R.; Weber, J. Induced Magnetic Fields in Aromatic [n]-Annulenes - Interpretation of NICS Tensor Components. Phys. Chem. Chem. Phys. 2004, 6, 273-276.
45. Schleyer, P. v. R. Introduction: Aromaticity. Chem. Rev. 2001, 101, 1115-1118.
46. Julg, A.; Françoise, P. Geometry of Nonalternant Hydrocarbons: its Influence on the Transition Energies, a New Definition of Aromaticity. Theor. Chim. Acta 1967, 8, 249-259.
47. (a) Hellmann, H. In Einfürung in die Quantenchemie; Franz Deuticke: Leipzig, 1937.
48. (b) Feynman, R. P. Forces in Molecules. Phys. Rev. 1939, 56, 340-343.
49. Wiberg, K. B. Basis Set Effects on Calculated Geometries: G-311++G** vs aug-cc-pVDZ. J. Comput. Chem. 2004, 25, 1342-1346.
50. Jeffrey, G. A.; Ruble, J. R.; McMullan, R. K.; Pople, J. A. The Crystal Structure of Deuterated Benzene. Proc. R. Soc. London 1987, A414, 47-57.
51. Lazzeretti, P. Assessment of Aromaticity via Molecular Response Properties. Phys. Chem. Chem. Phys. 2004, 6, 217-223.
52. Krygowski, T. M.; Ejsmont, K.; Stepień, B. T.; Cyrański, M. K.; Poater, J.; Solà, M. Relation between the Substituent Effect and Aromaticity. J. Org. Chem. 2004, 69, 6634-6640.
53. Krygowski, T. M.; Stepień, B. T.; Cyrański, M. K.; Ejsmont, K. Relation Between Resonance Energy and Substituent Resonance Effect in p-Phenols. J. Phys. Org. Chem. 2005, 18, 886-891.
54. Cyrański, M. K.; Krygowski, T. M.; Wisiorowski, M.; Hommes, N. J. R. v. E.; Schleyer, P. v. R. Global and Local Aromaticity in Porphyrins: An Analysis Based on Molecular Geometry and Nucleus Independent Chemical Shift. Angew. Chem., Int. Ed. Engl. 1998, 37, 177-180.