Summary
We have computationally studied the interaction modes, localization and orientation of a benzene (Bz) molecule on the surface of micelles formed by cetyltrimethylammonium salts CTAX. Experimental 1H-NMR data on complexation shifts induced by Bz on the polar head hydrogens and on the adjacent methylene hydrogens of CTAX have been interpreted using a computational approach that combines an automatic molecular docking procedure with a calculation module that accounts for NMR complexation shifts due to ring current diamagnetic anisotropy. Three different models were used to reduce the complexity of the micellar system. Computational results, in good agreement with available experimental data, point to a preferential localization of the Bz molecule along the CTAX alkyl tail, about 3.9 Å away from the charged nitrogen. The Bz molecular plane is predicted perpendicular to the C-H bonds of the alkyl tail. The good results obtained with the simplest model suggest that it could be used to study more complex systems involving surfactants endowed with molecular recognition or catalytic abilities.
Similar content being viewed by others
References
Chasman D.I., Protein Struct., 417 (2003)
KB. Lipkowitz (2001) J. Chromatogr. A. 906 417 Occurrence Handle10.1016/S0021-9673(00)00946-8 Occurrence Handle11215900
B.K. Shoichet S.L. Mc Govern B. Wai J. Irwin (2002) Curr. Opin. Chem. Biol. 6 439 Occurrence Handle10.1016/S1367-5931(02)00339-3 Occurrence Handle12133718
M. Cui X. Huang X. Luo J.M. Briggs R. Ji K. Chem J. Shen H. Jiang (2002) J. Med. Chem. 45 5249 Occurrence Handle10.1021/jm020082x Occurrence Handle12431052
P. Burkhard V. Hommel M. Sanner M.D. Walkinshaw (1999) J. Mol. Biol. 287 IssueID5 853 Occurrence Handle10.1006/jmbi.1999.2621 Occurrence Handle10222195
D.A. Gschwend A.C. Good I.D. Kuntz (1996) J. Mol. Recogn. 9 IssueID2 175 Occurrence Handle10.1002/(SICI)1099-1352(199603)9:2<175::AID-JMR260>3.0.CO;2-D
K. B. Lipkowitz (2000) Acc. Chem. Res. 33 555 Occurrence Handle10.1021/ar980115w Occurrence Handle10955986
Mittol, K.L. (Ed.) Micellization, Solubilization and Microemulsions, Vol. 1, Plenum Press, New York, 1997
Fendler, J. and Fendler, E., Catalysis in Micellar and Macromolecular Systems, Academic Press, New York, 1975
Wasan, D.T., Ginn, M.E. and Shah, D.O. (Eds.) Surfactants in Chemical/Process Engineering, Dekker, New York, 1988
D.C. Herman J.F. Artiola R.M. Miller (1995) Environ. Sci. Technol. 29 2280
G. Cerichelli S. Cerritelli M. Chiarini P. Maria ParticleDe A. Fontana (2002) Chem. Eur. J. 8 5204 Occurrence Handle10.1002/1521-3765(20021115)8:22<5204::AID-CHEM5204>3.0.CO;2-C
. Kabir-ud-Din S. Kumar P.S. Goyal (1996) Langmuir 12 1496 Occurrence Handle10.1021/la950677d
G.J. Duns L.W. Reeves D.W. Yang D.S. Williams (1995) J. Colloid Interf. Sci. 173 261 Occurrence Handle10.1006/jcis.1995.1325
P. Mukerjee J.R. Cardinal (1978) J. Phys. Chem. 82 1620 Occurrence Handle10.1021/j100503a010
L. Pauling (1936) J. Chem. Phys. 4 673 Occurrence Handle10.1063/1.1749766
C.W. Haigh R.B. Mallion (1980) Progr. Nucl. Magn. Reson. Spectrosc. 13 303 Occurrence Handle10.1016/0079-6565(79)80010-2
H. Stamm H. Jäckel (1989) J. Am. Chem. Soc. 111 6544 Occurrence Handle10.1021/ja00199a010
U. Fleisher W. Kutzelnigg P. Lazzaretti V. Mühlenkamp (1994) J. Am. Chem. Soc. 116 5289
J.A. Pople (1956) J. Chem. Phys. 24 1111 Occurrence Handle10.1063/1.1742701
J.S. Wangh R.W. Fessenden (1957) J. Am. Chem. Soc. 79 846 Occurrence Handle10.1021/ja01561a017
C.E. Johnson F.A. Bovey (1958) J. Chem. Phys. 29 101 Occurrence Handle10.1063/1.1744645
R. Abraham (1961) J. Mol. Phys. 4 145
R.J. Abraham C.J. Medforth (1987) Magn. Reson. Chem. 25 432 Occurrence Handle10.1002/mrc.1260250510
J.E. Cochran T.J. Parrott B.S. Withlock H.W. Withlock (1992) J. Am. Chem. Soc. 114 2269 Occurrence Handle10.1021/ja00032a057
M.J. Schneider (1993) Ree. Trav. Chim. Pays-Bas 112 412
G. Cerichelli G. Mancini (2000) Langmuir 16 182 Occurrence Handle10.1021/la990748z
S. Alcaro F. Gasparrini O. Iucani S. Mecucci D. Misiti M. Pierini C. Villani (2000) J. Comput. Chem. 21 515 Occurrence Handle10.1002/(SICI)1096-987X(200005)21:7<515::AID-JCC2>3.0.CO;2-5
C.D. Bruce M.L. Berkowitz L. Perera M.D.E. Forbes (2002) J. Phys. Chem. B 106 3788 Occurrence Handle10.1021/jp013616z
D. P. Tieleman D. Spoel Particlevan der H. J. C. Berendsen (2000) J. Phys. Chem. B, 104 6380
R.J. Abraham M. Canton M. Reid L. Griffiths (2000) J.␣Chem. Soc., Perkin Trans. 2 803
Alkorta, I. and Elguero, J., New J. Chem., (1998) 381
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Angelini, G., Cerichelli, G., Cerritelli, S. et al. An Effective Simulation of Aqueous Micellar Aggregates by Computational Models. J Comput Aided Mol Des 19, 259–269 (2005). https://doi.org/10.1007/s10822-005-4994-5
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s10822-005-4994-5