π-Electron delocalisation for intramolecular resonance assisted hydrogen bonds

Journal of Physical Organic Chemistry

Volumn 16, Issue 10, 2003, Pages 797-802

  Grabowski, Sławomir Janusz ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

electron delocalisation; ab initio calculations; Bader theory; Intramolecular hydrogen bonds; Resonance assisted hydrogen bonds

Indexed keywords

HYDROGEN BONDS; MONOMERS; NUMERICAL ANALYSIS; RESONANCE;

DELOCALIZATION;

ELECTRON TRANSITIONS;

EID: 0141954936     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.675     Document Type: Article

References (34)

1. Jeffrey GA. An Introduction to Hydrogen Bonding. Oxford University Press: New York, 1997.
2. Desiraju GR, Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford University Press: New York, 1999.
3. Jeffrey GA, Saenger W. Hydrogen Bonding in Biological Structures Springer-Verlag: Berlin,. 1991.
4. Rozas I, Alkorta I, Elguero J. J. Phys. Chem. A 2001; 105: 10462-10467.
5. Scheiner S. Hydrogen Bonding: A Theoretical Perspective. Oxford University Press: New York, 1997.
6. Gilli G, Bellucci F, Ferretti V, Bertolasi V. J. Am. Chem. Soc. 1989; 111: 1023-1028.
7. Rybarczyk-Pirek AJ, Grabowski SJ, Małecka M, Nawrot-Modranka J. J. Phys. Chem. A 2002; 106: 11956-11962.
8. González L, Mó O, Yáñez M. J. Phys. Chem. 1997; 101: 9710-9719.
9. González L, Mó O, Yáñez. J. Org. Chem. 1999; 64: 2314-2321.
10. Latajka Z, Scheiner S. J. Phys. Chem. 1992; 96: 9764.
11. Grabowski SJ. J. Mol. Struct. 2001; 562: 137-143.
12. Buemi G. J. Mol. Struct. (Theochem). 2000; 499: 21-34.
13. Buemi G. Chem. Phys. 2002; 277: 241-256.
14. Madsen GKH, Iversen BB, Larsen FK, Kapon M, Reisner GM, Herbstein FH. J. Am. Chem. Soc. 1998; 120: 10040-10045.
15. Garcia-Viloca M, González-Lafont A, Lluch JM. J. Am. Chem. Soc. 1997; 119: 1081-1086.
16. Garcia-Viloca M, Gelabert R, González-Lafont A, Moreno M, Lluch JM. J. Phys. Chem. A 1997; 101: 8727-8733.
17. Bader RFW. Atoms in Molecules. A Quantum Theory. Oxford University Press: New York, 1990.
18. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin LR, Fox DJ, Keith T, Al.-Laham MA, Peng CY, Nanayakkara A, Gonzalez G, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98; Revision A.6. Gaussian, Inc.: Pittsburgh, PA, 1998.
19. Clark T, Chandrasekhar J, Spitznagel G, Schleyer P. V. R. J. Comput. Chem. 1983; 4: 294.
20. Frisch MJ, Pople JA, Binkley JS. J. Chem. Phys. 1984; 80: 3265.
21. Møller C, Plesset MS. Phys. Rev. 1934; 46: 618.
22. AIM2000 designed by Friedrieh Biegler-König, University of Applied Sciences, Bielefeld, Germany.
23. Cuma M, Scheiner S, Kar T. J. Mol. Struct. (Theochem)1999; 467: 37-49.
24. Craw JS, Bacskay J. J. Chem. Soc. Faraday Trans. 1992; 88: 2315.
25. Buemi G, Zuccarello F. J. Mol. Struct. (Theochem) 2002; 581: 71-85.
26. Wojtulewski S, Grabowski SJ. J. Mol. Struct. 2003; 645: 287-294.
27. Cioslowski J, Surján P. J. Mol. Struct. (Theochem) 1992; 255: 9-33.
28. Mó O, Yánez M, Elguero J. J. Chem. Phys. 1992; 97: 6628.
29. Mó O, Yánez M, Elguero J. J. Mol. Struct. (Theochem) 1994; 314: 73.
30. Grabowski SJ. J. Phys. Chem. A 2001; 105: 10739.
31. Sanz P, Yánez M, Mó O. J. Phys. Chem. A 2002; 106: 4661-4668.
32. Krygowski TM, Stepień B, Anulewicz-Ostrowska R, Dziembowska T. Tetrahedron 1999; 55: 5457-5464.
33. Kruszewski J, Krygowski TM. Tetrahedron Lett. 1972; 38.
34. Krygowski TM. J. Chem. Inf. Comput. Sci. 1993; 33: 70-78.