Resonance-assisted hydrogen bonding in terms of substituent effect

Tetrahedron

Volumn 65, Issue 10, 2009, Pages 2010-2014

  Krygowski, Tadeusz M ^a   Zachara Horeglad, Joanna E ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

Electron delocalization; Hydrogen bond; RAHB; Substituent effect

Indexed keywords

MALONALDEHYDE; PROTON; SALICYLALDEHYDE;

ARTICLE; CONTROLLED STUDY; ELECTRICITY; ELECTRON; ELECTRON TRANSPORT; HYDROGEN BOND; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON TRANSPORT; QUANTUM MECHANICS; RESONANCE ASSISTED HYDROGEN BOND; SUBSTITUTION REACTION;

EID: 59249109195     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.006     Document Type: Article

References (45)

1. In: Scheiner S. (Ed). Intermolecular Interactions: From van der Waals to Strongly Bound Complexes (1997), Wiley, New York, NY
2. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford University Press, New York, NY
3. Gerlt J.A., Kreevoy M.M., Cleland W.W., and Frey P.A. Chem. Biol. 4 (1997) 259-267
4. Perrin C.L., and Nielson J.B. Annu. Rev. Phys. Chem. 48 (1997) 511-544
5. Desiraju G.R. Acc. Chem. Res. 35 (2002) 565-573
6. Meyer E.A., Castellano R.K., and Diederich F. Angew. Chem., Int. Ed. 42 (2003) 1210-1250
7. Sobczyk L., Grabowski S.J., and Krygowski T.M. Chem. Rev. 105 (2005) 3513-3560
8. Krygowski T.M., and Szatyłowicz H. Trends Org. Chem. 11 (2006) 37-53
9. Pauling L. The Nature of the Chemical Bond (1960), Cornell University Press, New York, NY
10. Pure Appl. Chem. 71 (1999) 1919-1981
11. Gilli G., Belluci F., Ferretti V., and Bertolasi V. J. Am. Chem. Soc. 111 (1989) 1023-1028
12. Gilli G., and Gilli P. J. Mol. Struct. 552 (2000) 1-15
13. Williams D.E., Dunke W.L., and Rundle R.E. Acta Crystallogr. 15 (1962) 627-635
14. Ogoshi H., and Yoshida Z. J. Chem. Soc. D: Chem. Commun. (1970) 176-177
15. Scheiner S. Hydrogen Bonding. A Theoretical Perspective (1997), Oxford University Press, Oxford
16. Glendening E.D., Badenhoop J.K., and Weinhold F. J. Comput. Chem. 19 (1998) 628-646
17. Weinhold F., and Landis C.R. Valency and Bonding (2005), Cambridge University Press, Cambridge
18. Alkorta I., Elguero J., Mó O., Yáñez M., and Del Bene J.E. Mol. Phys. 102 (2004) 2563-2574
19. Alkorta I., Elguero J., Mó O., Yáñez M., and Del Bene J.E. Chem. Phys. Lett. 411 (2002) 411-415
20. Sanz P., Mó O., Yáñez M., and Elguero J. Chem.-Eur. J. 14 (2008) 4225-4232
21. Sanz P., Mó O., Yáñez M., and Elguero J. ChemPhysChem 8 (2007) 1950-1958
22. In: Grabowski S.J. (Ed). Hydrogen Bonding-New Insights. Series: Challenges and Advances in Computational Chemistry and Physics Vol. 3 (2006), Springer, Dordrecht
23. Grabowski S.J. J. Phys. Org. Chem. 16 (2003) 797-802
24. Grabowski S.J. J. Mol. Struct. 562 (2001) 137-143
25. Cuma M., Scheiner S., and Kar T. J. Mol. Struct. (THEOCHEM) 467 (1999) 37-49
26. Krygowski T.M., Zachara J.E., and Szatyłowicz H. J. Phys. Org. Chem. 18 (2005) 110-114
27. Grabowski S.J. J. Phys. Org. Chem. 17 (2004) 18-31
28. Hammett L.P. Physical Organic Chemistry (1940), McGraw-Hill, New York, NY
29. Exner O. In: Chapman N.B., and Shorter J. (Eds). Advances in Linear Free Energy Relationships (1972), Plenum, London 1-69
30. Charton M. Prog. Phys. Org. Chem. 10 (1973) 81-204
31. Charton M. Prog. Phys. Org. Chem. 13 (1981) 119-251
32. Hansch C., Leo A., and Taft W.R. Chem. Rev. 91 (1991) 165-195
33. Krygowski T.M., and Ste{ogonek}pień B.T. Chem. Rev. 105 (2005) 3482-3512
34. Jaffe H.H. Chem. Rev. 53 (1953) 191-261
35. Shorter J. Pure Appl. Chem. 66 (1994) 2451-2468
36. Shorter J. Pure Appl. Chem. 69 (1997) 2497-2510
37. Krygowski T.M., Zachara-Horeglad J.E., Palusiak M., Pelloni S., and Lazzeretti P. J. Org. Chem. 73 (2008) 2138-2145
38. Krygowski T.M., Zachara J., and Szatyłowicz H. J. Org. Chem. 69 (2004) 7038-7043
39. Ste{ogonek}pień B.T., Cyrański M.K., and Krygowski T.M. Chem. Phys. Lett. 350 (2001) 537-542
40. Krygowski T.M. J. Chem. Inf. Comput. Sci. 33 (1993) 70-78
41. Krygowski T.M., Szatyłowicz H., and Zachara J.E. J. Chem. Inf. Model. 45 (2005) 652-656
42. Krygowski T.M., Szatyłowicz H., and Zachara J.E. J. Chem. Inf. Comput. Sci. 44 (2004) 2077-2082
43. Bertolasi V., Pretto L., Ferretti V., Gilli P., and Gilli G. Acta Crystallogr., Sect. B 62 (2006) 1112-1120
44. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi 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 G.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., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford, CT
45. Pauling L. J. Am. Chem. Soc. 69 (1947) 542-553