The "hydrazinoturn" hydrogen bonding network in hydrazinopeptides and aza-β3-peptides as probed by an AIM topological analysis of the electronic density

Journal of Molecular Structure: THEOCHEM

Volumn 869, Issue 1-3, 2008, Pages 41-46

  Simo, Cyrille ^a   Salaün, Arnaud ^a   Arnarez, Clément ^b   Delemotte, Lucie ^b   Haegy, Alexandre ^c   Kachmar, Ali ^c   Laurent, Adèle D ^b   Thomas, Jennifer ^b   Jamart Grégoire, Brigitte ^a   Le Grel, Philippe ^d   Hocquet, Alexandre ^a  

^a LAB DE CHIM PHYS MACROMOLECULAIRE   (France)

^b NANCY UNIVERSITÉ   (France)

^c CNRS   (France)

^d INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

AIM; Aza 3 peptides; Bifurcated hydrogen bonding; Hydrazinopeptides; Hydrazinoturn

Indexed keywords

EID: 54249161321     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2008.08.019     Document Type: Article

References (39)

1. Lelais G., and Seebach D. Helv. Chim. Acta 86 (2003) 4152-4168
2. Salaün A., et al. J. Org. Chem. 70 (2005) 6499-6502
3. Cheguillaume A., et al. J. Org. Chem. 66 (2001) 4923-4929
4. Gellman S.H. Acc. Chem. Res. 31 (1998) 171-180
5. Hill D.J., et al. Chem. Rev. 101 (2001) 3893-4012
6. Le Grel P., and Guichard G. Foldamers based on Remote Intrastrand Interactions in Foldamers. In: Huc I., and Hecht S. (Eds) (2007), Wiley-VCH Verlag, Weinheim 35-74
7. Aubry A., et al. Biopolymers 31 (1991) 793-801
8. Gunther R., and Hofmann H. J. Am. Chem. Soc. 123 (2001) 247-255
9. Salaun A., et al. J. Org. Chem. 71 (2006) 150-158
10. Bader R.F.W. Atoms In Molecules. A Quantum Theory (1990), Clarendon, Oxford
11. Carroll M.T., and Bader R.F.W. Mol. Phys. 65 (1988) 695
12. Koch U., and Popelier P.L.A.J. Phys. Chem. 99 (1995) 9747
13. Popelier P.L.A.J. Phys. Chem. A 102 (1998) 1873
14. Hocquet A. Phys. Chem. Chem. Phys. 03 (2001) 3192-3199
15. Louit G., Hocquet A., and Ghomi M. Phys. Chem. Chem. Phys. 4 (2002) 3843-3848
16. Yurenko Y.P., et al. Chem. Phys. Lett. 447 (2007) 140-146
17. Yurenko Y.P., et al. J. Phys. Chem. B 112 (2008) 1240
18. Yurenko Y.P., et al. J. Phys. Chem. B 111 (2007) 6263-6271
19. Yurenko Y.P., et al. J. Phys. Chem. B 111 (2007) 9655-9663
20. Louit G., et al. PhysChemComm 5 (2002) 94-98
21. Becke A.D. J. Chem. Phys. A 98 (1993) 5648
22. Miehlich B., Savin A., Stoll H., and Preuss H. Chem. Phys. Lett. 157 (1989) 200
23. Lee C., Yang W., and Parr R.G. Phys. Rev. 37 (1988) 785
24. Vosko S.H., Wilk L., and Nusair M. Can. J. Phys. 58 (1980) 1200
25. Ditchfield R., Hehre W.J., and Pople J.A. J. Chem. Phys. 54 (1971) 724
26. Hehre W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 56 (1972) 2257
27. Hariharan P.C., and Pople J.A. Mol. Phys. 27 (1974) 209
28. Gordon M.S. Chem. Phys. Lett. 76 (1980) 163
29. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
30. Frisch M.J., Pople J.A., and Binkley J.S. J. Chem. Phys. 80 (1984) 3265
31. Gaussian 03, Revision C.02, 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, [...]
32. Csaszar P., and Pulay P. J. Mol. Struct. (Theochem) 114 (1984) 31
33. Farkas O., and Schlegel H.B. J. Chem. Phys. 111 (1999) 10806
34. GaussView, Version 3.0, Roy Dennington II, Todd Keith, John Millam, Ken Eppinnett, W. Lee Hovell, Ray Gilliland, Semichem, Inc., Shawnee Mission, KS, 2003.
35. Biegler-König F., Schönbohm J., and Bayles D. J. Comput. Chem. 22 (2001) 545-559
36. Aicken F.M., and Popelier P.L.A. Can. J. Chem. 78 (2000) 415
37. Song J.-W., Lee H.-J., Choi Y.-S., and Yoon C.-J. J. Phys. Chem. A 110 5 (2006) 2065-2071
38. Song L., Liu M., Wu W., Zhang Q., and Mo Y. J. Chem. Theory Comput. 1 3 (2005) 394-402
39. Grana A.M., and Mosquera R.A. J. Mol. Struct. 556 1-3 (2000) 69-76