Comparative studies on CHâ"̄F- hydrogen bond formation in benzene and exocyclically substituted pentafulvene derivatives

Journal of Physical Organic Chemistry

Volumn 26, Issue 7, 2013, Pages 575-582

  Oziminski, Wojciech P ^a   Krygowski, Tadeusz M ^b  

^a NATIONAL MEDICINES INSTITUTE   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

benzene; fulvene; hydrogen bond; substituent effect

Indexed keywords

BENZENE DERIVATIVES; BOND DISSOCIATION ENERGIES; COMPARATIVE STUDIES; FULVENE; HYDROGEN-BOND FORMATION; PARA-SUBSTITUTED BENZENES; STABILIZATION ENERGY; SUBSTITUENT EFFECT;

BOND STRENGTH (CHEMICAL); CHLORINE COMPOUNDS; COPYRIGHTS; DENSITY FUNCTIONAL THEORY; HYDROGEN BONDS; STABILIZATION;

BENZENE;

EID: 84879221024     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.3134     Document Type: Article

References (47)

1. D. Lloyd, The Chemistry of Conjugated Compounds: To Be or Not to Be Like Benzene, Wiley, Chichester, 1990.
2. V. I. Minkin, M. N. Glukhovtsev, B. Y. Simkin, Aromaticity and Antiaromaticity-Electronic and Structural Aspects, Wiley-Interscience Publ, New York, 1994.
3. A. Streitwieser Jr., Molecular Orbital Theory for Organic Chemists, J. Wiley, New York, 1961, 298ff.
4. P. V. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317.
5. M. K. Cyrański, Chem. Rev. 2005, 105; isodesmic reaction #11 in Table 13, p 3793
6. B. T. Stepien, T. M. Krygowski, M. K. Cyranski, J. Org. Chem. 2002, 67, 5987.
7. L. P. Hammett, Chem. Rev. 1935, 17, 125.
8. L. P. Hammett, Physical Organic Chemistry, McGraw-Hill, New York, 1940.
9. H. H. Jaffe, Chem. Rev. 1953, 53, 191.
10. O. Exner, in: Advances in Linear Free Energy Relationships (Eds:, N. B. Chapman, J. Shorter,), Plenum Press, New York, 1972, 1.
11. O. Exner, in: Correlation Analysis-Recent Advances (Eds:, N. B. Chapman, J. Shorter,), Plenum Press, NY, 1978, 439.
12. M. Charton, in: Progress in Physical Organic Chemistry, vol 10 (Ed:, A. Streitwieser,), J. Wiley, New York, 1973, 61.
13. M. Palusiak, T. M. Krygowski, New J. Chem. 2009, 33, 1753.
14. H. Szatyłowicz, T. M. Krygowski, M. Palusiak, J. Poater, M. Sola, J. Org. Chem. 2011, 76, 550.
15. M. Shahamirian, M. K. Cyrański, T. M. Krygowski, J. Phys. Chem. A, 2011, 115, 550.
16. T. M. Krygowski, M. A. Dobrowolski, M. K. Cyranski, W. P. Oziminski, P. Bultinck, Comp. Theor. Chem. 2012, 984, 36.
17. G. W. Wheland, D. E. Mann, J. Chem. Phys. 1949, 17, 264.
18. E. Kleinpeter, A. Fettke, Tetr. Lett. 2008, 49, 2776.
19. S. Noorizadech, E. Shakerzadech, Comp. Theor. Chem. 2011, 964, 141.
20. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
21. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623.
22. A. Pross, L. Radom, R. W. Taft, J. Org. Chem. 1980, 45, 818.
23. W. J. Hehre, L. Radom, P. v. R. Schleyer, A. J. Pople, Ab initio Molecular Orbital Theory, J. Wiley & Sons, NY, 1986, 360ff.
24. L. Sobczyk, S. J. Grabowski, T. M. Krygowski, Chem. Rev. 2005, 105, 3513.
25. S. J. Grabowski, Chem. Rev. 2011, 111, 2597.
26. E. Espinosa, I. Alkorta, J. Elguero, E. Molins, J. Chem. Phys. 2002, 117, 5529.
27. T. A. Keith, AIMAll (Version 10.12.13), TK Gristmill Software, Overland Park KS, USA, 2011, (aim.tkgristmill.com).
28. W. P. Oziminski, J. C. Dobrowolski, J. Phys. Org. Chem. 2009, 22, 769.
29. N. Sadlej-Sosnowska, Chem. Phys. Lett. 2007, 447, 192.
30. N. Sadlej-Sosnowska, K. Murlowska, Pol. J. Chem. 2008, 82, 935.
31. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford CT, 2004.
32. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.
33. H. H. Bilker, N. M. M. Nibbering, D. Espinosa, F. Mongin, M. Schlouer, Tetrahedron Lett. 1997, 38, 8519.
34. M. Namazian, M. L. Coote, J. Fluor. Chem. 2009, 130, 621.
35. T. M. Krygowski, J. E. Zachara, H. Szatyłowicz, J. Phys. Org. Chem. 2005, 18, 110.
36. O. A. Stasyuk, H. Szatyłowicz, T. M. Krygowski, J. Org. Chem. 2012, 77, 4035.
37. A. Pross, L. Radom, R. W. Taft, J. Org. Chem. 1980, 45, 818.
38. W. J. Hehre, L. Radom, P. v. R. Schleyer, A. J. Pople, Ab initio Molecular Orbital Theory, J. Wiley & Sons, N. York, 1986, 360ff.
39. F. Weinhold, C. Landis, Valency and Bonding, A Natural Bond Orbital Donor-Acceptor Perspective, Cambridge University Press, Cambridge, 2005, 595-596.
40. M. Palusiak, T. M. Krygowski, New J. Chem. 2009, 33, 1753.
41. P. Cysewski, T. Jelinski, T. M. Krygowski, W. P. Oziminski, Current Org. Chem. 2012, 16, 1920.
42. T. M. Krygowski, M. A. Dobrowolski, M. K. Cyranski, W. P. Oziminski, P. Bultinck, Comp. Theor. Chem. 2012, 984, 36.
43. J. Shorter, Correlation Analysis in Organic Chemistry: An Introduction to Linear Free-Energy Relationships, Clarendon Press, Oxford, 1973, Chapter 2.
44. Advances in Linear Free Energy Relationships (Eds:, N. B. Chapman, J. Shorter,), Plenum Press, London and New York, 1972.
45. W. P. Oziminski, T. M. Krygowski, J. Mol. Model. 2011, 17, 565.
46. T. M. Krygowski, N. Sadlej-Sosnowska, Chem.Phys. Lett. 2009, 476, 191.
47. T. M. Krygowski, N. Sadlej-Sosnowska, Struct. Chem. 2011, 22, 17. Warsaw University