DFT and AIM studies on two-ring resonance assisted hydrogen bonds

Journal of Molecular Structure: THEOCHEM

Volumn 621, Issue 3, 2003, Pages 285-291

  Wojtulewski, Sławomir ^a   Grabowski, Sławomir J ^a,b  

^a UNIVERSITY OF BIALYSTOK   (Poland)

^b UNIVERSITY OF LODZ   (Poland)

Author keywords

2,4 Dihydroxybut 2 ene 4 dial; Bond critical points; DFT calculations; Resonance assisted hydrogen bonds; Ring critical points; The Bader theory

Indexed keywords

2,4 DIHYDROXYBUT 2 ENE 4 DIAL; ALKENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CORRELATION COEFFICIENT; ENERGY; HYDROGEN BOND; PROTON TRANSPORT; THEORETICAL STUDY;

EID: 0037470279     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(02)00608-5     Document Type: Article

References (37)

1. G.A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer, Berlin, 1991.
2. G.R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, New York, 1999.
3. J.D. Dunitz, X-ray Analysis and the Structure of Organic Molecules, Cornell University Press, Ithaca, London, 1979.
4. G.R. Desiraju, Crystal Engineering - the Design of Organic Solids, Elsevier, Amsterdam, 1989.
5. M. Ichikawa, Acta Crystallogr. B34 (1978) 2074.
6. S.J. Grabowski, T.M. Krygowski, Tetrahedron 54 (1998) 5683 and references cited therein.
7. S.J. Grabowski, Chem. Phys. Lett. 338 (2001) 361.
8. S.J. Grabowski, Tetrahedron 54 (1998) 10153.
9. M. Palusiak, S.J. Grabowski, J. Mol. Struct. (2002) in press.
10. J.W. Larson, T.B. McMahon, J. Am. Chem. Soc. 103 (1983) 2944.
11. J.W. Larson, T.B. McMahon, J. Am. Chem. Soc. 106 (1984) 517.
12. V. Bertolasi, P. Gilli, V. Ferretti, G. Gilli, J. Am. Chem. Soc. 113 (1991) 4917.
13. S.J. Grabowski, J. Phys. Chem. A 105 (2001) 10739.
14. R.F.W. Bader, Atoms in Molecules. A Quantum Theory, Oxford University Press, New York, 1990.
15. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, L.R. Martin, D.J. Fox, T. Keith, M.A. Al.-Laham, C.Y. Peng, A. Nanayakkara, G. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, GAUSSIAN 98, Revision A.6, Gaussian Inc., Pittsburgh, PA, 1998.
16. R. Krishnam, J.S. Binkley, R. Seeger, J.A. Pople, J. Chem. Phys. 80 (1984) 3265.
17. A.D. Becke, J. Chem. Phys. 98 (1993) 5648.
18. AIM2000 designed by Friedrich Biegler-König, University of Applied Sciences, Bielefeld, Germany.
19. F.W. Biegler-König, R.F.W. Bader, Y.H. Tang, J. Comput. Chem. 3 (1982) 317.
20. R.F.W. Bader, Y.H. Tang, Y. Tal, F.W. Biegler-König, J. Am. Chem. Soc. 104 (1984) 946.
21. S.J. Grabowski, J. Mol. Struct. 562 (2001) 137.
22. M. Cuma, S. Scheiner, T. Kar, J. Mol. Struct. (Theochem) 467 (1999) 37.
23. W.J. Hehre, L. Radom, P.v.R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York, 1986.
24. I. Rozas, I. Alkorta, J. Elguero, J. Phys. Chem. A 105 (2001) 10462.
25. M.T. Carrol, C. Chang, R.F.W. Bader, Mol. Phys. 63 (1988) 387.
26. M.T. Carrol, R.F.W. Bader, Mol. Phys. 65 (1988) 695.
27. U. Koch, P. Popelier, J. Phys. Chem. 99 (1995) 9747.
28. O. Mó, M. Yáñez, J. Elguero, J. Chem. Phys. 97 (1992) 6628.
29. O. Mó, M. Yáñez, J. Elguero, J. Mol. Struct. (Theochem) 314 (1994) 73.
30. O. Mó, M. Yáñez, I. Rozas, J. Elguero, J. Chem. Phys. 100 (1994) 2871.
31. E. Espinosa, M. Souhassou, H. Lachekar, C. Lecomte, Acta Crystallogr. B55 (1999) 563.
32. Y.A. Abramov, Acta Crystallogr. A53 (1997) 264.
33. E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett. 285 (1998) 170.
34. E. Espinosa, I. Alkorta, I. Rozas, J. Elguero, E. Molins, Chem. Phys. Lett. 336 (2001) 457.
35. D. Quiñonero, A. Frontera, P. Ballester, C. Garau, A. Costa, P.M. Deyà, Chem. Phys. Lett. 339 (2001) 369.
36. S.J. Grabowski, Monatsch. für Chem. 133 (2002) 1373.
37. P. Popelier, Atoms in Molecules. An Introduction, Prentice-Hall, Pearson Education Limited, Englewood Cliffs, NJ, 2000.