Interplay between hydrogen-bond formation and multicenter π-electron delocalization: Intramolecular hydrogen bonds

Journal of Physical Chemistry A

Volumn 112, Issue 42, 2008, Pages 10689-10696

  Lenain, Pieterjan ^a,b   Mandado, Marcos ^a   Mosquera, Ricardo A ^a   Bultinck, Patrick ^b  

^a UNIVERSITY OF VIGO   (Spain)

^b GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ATOMIC PHYSICS; ATOMS; BINDING SITES; BOND STRENGTH (CHEMICAL); ELECTRONS; HYDROGEN; NONMETALS; OXYGEN; QUANTUM THEORY; SULFUR;

AROMATICITY; BOND FORMATIONS; BOND STRENGTHS; DELOCALIZATION; DELOCALIZATION INDEXES; INTRAMOLECULAR HYDROGEN BONDS; INTRAMOLECULAR HYDROGENS; MALONALDEHYDE; MOLECULAR ENERGIES; QUANTUM THEORY OF ATOMS IN MOLECULES; RELATIVE ENERGIES; RELATIVE STRENGTHS; RESONANCE MODELS;

HYDROGEN BONDS;

EID: 55649091440     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp805084n     Document Type: Article

References (29)

1. Lenain, P.; Mandado, M.; Mosquera, R. A.; Bultinck, P. J. Phys. Chem. A, 2008, 112, 7898.
2. Sobczyk, L.; Grabowski, S. J.; Krygowski, T. M. Chem. Rev 2005, 105, 3513, and references therein.
3. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, Oxford, 1997.
4. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, New York, Heidelberg, 1991.
5. Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511.
6. Murrel, J. M.; Kettle, S. F.; Tedder, J. M. The Chemical Bond; John Wiley & Sons, Chichester, 1985.
7. Sing, U. C.; Kollman, P. A. J. Chem. Phys. 1985, 83, 4033.
8. Spackman, M. A. J. Chem. Phys. 1986, 85, 6587.
9. Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1.
10. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, 1990.
11. Grabowski, S. J. J. Phys. Org. Chem. 2003, 16, 797.
12. Palusiak, M.; Simon, S.; Sola, M. J. Org. Chem. 2006, 71, 5241.
13. Mandado, M.; González-Moa, M. J.; Mosquera, R. A. J. Comput. Chem. 2007, 28, 127.
14. Bultinck, P.; Michel, R.; Ponec, R.; Van Gheluwe, B.; Carbö-Dorca, R.; Popelier, P. J. Phys. Chem. A 2006, 110, 7642.
15. Mandado, M.; Otero, N.; Mosquera, R. A. Tetrahedron 2006, 62, 12204.
16. Mandado, M.; Krishtal, A.; Van Alsenoy, C.; Bultinck, P.; Hermida-Ramon, J. M. J. Phys. Chem. A 2007, 111, 11885.
17. Caramori, G. F.; de Oliveira, K. T.; Galembeck, S. E.; Bultinck, P.; Constantino, M. G. J. Org. Chem. 2007, 72, 76.
18. Ponec, R.; Bultinck, P.; Gallegos-Saliner, A. J. Phys. Chem. A 2005, 109, 6606.
19. Angyan, J. G.; Loos, M.; Mayer, I. J. Phys. Chem. 1994, 98, 5244.
20. Jabłoński, M.; Kaczmarek, M.; Sadlej, A. J. J. Phys. Chem. A 2006, 110, 10890.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J. 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, 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.
22. AIMPAC: A suite of Programs for the Theory of Atoms in Molecules; Bader, R. F. W., and coworkers, Eds.; McMaster University: Hamilton, ON, Canada: contact: bader@mcmail.cis.mcmaster.ca.
23. Alkorta, I.; Elguero, J.; Mo, O.; Yáñez, M.; del Bene, J. E. Mol. Phys. 2004, 102, 2563.
24. Alkorta, I.; Elguero, J.: Mó, O.; Yáñez., M.; del Bene, J. E. Chem. Phys. Lett. 2005, 411, 411.
25. Wojtulewski, S.; Grabowski, S. J. Chem. Phys. Lett. 2003, 378, 388.
26. Clar. E. The Aromatic Sextet; 3. Wiley & Sons: London, 1972.
27. Mandado, M.; González.-Moa, M. J.; Mosquera, R. A. J. Comput. Chem. 2007, 28, 1625.
28. Randié, M. Chem. Rev. 2003, 103, 3449.
29. Mandado, M.; González.-Moa, M. J.; Mosquera, R. A. ChemPhysChem 2007, 8, 696.