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

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 7038-7043

  Krygowski, Tadeusz M ^a   Zachara, Joanna E ^a   Szatylowicz, Halina ^b  

^a UNIVERSITY OF WARSAW   (Poland)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; MOLECULAR ORIENTATION; STABILIZATION;

BOND LENGTH; LINEARITY; MOIETY; MOLECULAR GEOMETRY;

PHENOLS;

4 NITROPHENOL; PHENOL DERIVATIVE;

AB INITIO CALCULATION; ANALYTIC METHOD; ANISOTROPY; AROMATIZATION; ARTICLE; CHEMICAL ANALYSIS; COMPLEX FORMATION; GEOMETRY; HYDROGEN BOND; MAGNETISM; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 5444269375     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049245a     Document Type: Article

References (55)

1. Bergmann, E. D., Pullman, B., Eds. Aromaticity, Pseudoaromaticity, Antiaromaticity; Proceedings of an International Symposium, Jerusalem 1970, Israel Academy of Sciences and Humanities: Jerusalem, 1971.
2. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Ya. Aromaticity and Antiaromaticity-Electronic and Structural Aspects; Wiley: New York, 1994.
3. Special issue on aromaticity: Schleyer, P. v. R., Guest Ed. Chem. Rev. 2001, 707, 1115-1566.
4. Krygowski, T. M.; Cyranski M. K. Phys. Chem. Chem. Phys. 2003, 6, 249-255.
5. Institute for Scientific Information, Philadelphia (1996-2003). Retrieved 1 January 2004.
6. Krygowski, T. M.; Cyranski, M. K.; Czarnocki, Z.; Häfelinger, G.; Katritzky, A. R. Tetrahedron 2000, 56, 1783-1796.
7. Krygowski, T. M.; Cyranski, M. K. Chem. Rev. 2001, 707, 1385-1420.
8. Pauling, L. The Nature of the Chemical Bond and Structure of Molecules in Crystals; Cornell University Press: Ithaca, 1960; pp 188ff.
9. Cyranski, M. K.; Krygowski, T. M.; Katritzky, A. R.; Schleyer, P. v. R. J. Org. Chem. 2002, 67, 1333-1338.
10. Cyranski, M. K.; Schleyer, P. v. R.; Krygowski, T. M.; Jiao, H.; Hohlneicher, G. Tetrahedron 2003, 59, 1657-1665.
11. Julg, A.; Françoise, Ph. Theor. Chim. Acta 1967, 8, 249-259.
12. Kruszewski, J.; Krygowski, T. M. Tetrahedron Lett. 1972, 3839-3842.
13. Bird, C. W. Tetrahedron 1985, 41, 1409-1414.
14. Krygowski, T. M. J. Chem. Inf. Comput. Sci. 1993, 33, 70-78.
15. (a) Flygare, W. H. Chem. Rev. 1974, 74, 653-687.
16. (b) Dauben, H. J.; Wilson, J. D.; Laity, J. L. J. Am. Chem. Soc. 1968, 90, 811-813.
17. (c) Dauben, H. J.; Wilson, J. D.; Laity, J. L. J. Am. Chem. Soc. 1969, 91, 1991-1998.
18. (d) Dauben, H. J.; Wilson, J. D.; Laity, J. L. In Non-Benzenoid Aromatic Compounds; Snyder, J. P., Ed.; Academic Press: New York, 1971; Vol. 2.
19. For recent review, see: Lazzeretti, P. Prog. Nucl. Magn. Reson. Spectrosc. 2000, 36, 1-88.
20. Wannere, C. S.; Schleyer, P. v. R. Org. Lett. 2003, 5, 605-608.
21. Ferraro, M. B.; Lazzeretti, P.; Viglione, R. G.; Zanasi, R. Chem. Phys. Lett. 2004, 390, 268-271.
22. (a) Elser, V.; Haddon, R. C. Nature (London) 1987, 325, 792-794.
23. (b) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317-6318.
24. Ferraro, M. B.; Lazzeretti, P.; Viglione, R. G.; Zanasi, R. Chem. Phys. Lett. 2004, 390, 268-271.
25. Corminboeuf, C.; Heine, T.; Seifert, G.; Schleyer, P. v. R.; Weber, J. Phys. Chem. Chem. Phys. 2004, 6, 273-276.
26. (a) Breslow, R. Angew. Chem. 1968, 80, 573-578.
27. (b) Lloyd, D.; Marshall, D. R. Angew. Chem., Int. Ed. Engl. 1972, 11, 404-408.
28. Smith, B. M.; March, J. March's Advanced Organic Chemistry, 5th ed.; Wiley: New York, 2001; p 46.
29. Schleyer, P. v. R.; Jiao, H. Pure Appl. Chem. 1996, 68, 209-218.
30. Krygowski, T. M.; Ciesielski, A.; Bird, C. W.; Kotschy A. J. Chem. Inf. Comput. Sci. 1995, 35, 203-210.
31. Howard, S. T.; Krygowski, T. M. Can. J. Chem. 1997, 75, 1174-1181.
32. (a) Clar, E. Polycyclic Hydrocarbons; Academic Press, Inc.: London, 1964; Vols. 1 and 2.
33. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972.
34. Katritzky, A. R.; Karelson, M.; Wells, A. P. J. Org. Chem. 1996, 61, 1619-1623.
35. Cyranski, M. K.; Gilski, M.; Jaskólski, M.; Krygowski T. M. J. Org. Chem. 2003, 68, 8607-8613.
36. Shorter, J. Pure Appl. Chem. 1994, 66, 2451-2468.
37. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
38. Krygowski, T. M.; Zachara J. E.; Szatylowicz H. J. Phys. Org. Chem. 2004, 17, in press.
39. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
40. (b) Becke, A. D. J. Phys. Chem. 1993, 98, 1372-1377.
41. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
42. (d) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
43. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Revision A.7; Gaussian Inc.: Pittsburgh, PA, 1998.
44. Schleyer, P. v. R.; Manoharan, M.; Wang, Z.-X.; Kiran, B.; Jiao H.; Puchta, R.; Hommes, N. J. R. v. E. Org. Lett. 2001, 3, 2465-2468.
45. Systat Software Inc., Richmond, CA.
46. Pross A.; Radom L.; Taft R. W. J. Org. Chem. 1980, 45, 818-826.
47. George, P.; Trachtmann, M.; Bock, C. W.; Brett, A. M. Theor. Chim. Acta 1975, 38, 121-129.
48. Cyranski, M. K.; Krygowski, T. M.; Wisiorowski, M.; Hommes N. J. R. v. E.; Schleyer, P. v. R. Angew. Chem., Int. Ed. 1998, 37, 177-180.
49. (a) Katritzky, A. R.; Barczynski, P.; Musumurra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc. 1989, 777, 7-15.
50. (b) Jug, K.; Koester, A. J. Phys. Org. Chem. 1991, 4, 163-169.
51. (c) Katritzky, A. R.; Karelson, M.; Sild, S.; Krygowski, T. M.; Jug K. J. Org. Chem. 1998, 63, 5228-5231.
52. (d) Schleyer, P. v. R.; Freeman, P. K.; Jiao H.; Goldfuyß, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 337-340.
53. Lazzeretti, P. Phys. Chem. Chem. Phys. 2004, 6, 217-223.
54. Glukhovtsev M. N.; Schleyer P. v. R. Chem. Phys. Lett. 1992, 798, 547-554.
55. Haddon, R. C.; Raghavachari, K. J. Am. Chem. Soc. 1985, 707, 289-298.