Information Textbooks Media Resources

Portraying the Structure of Micelles

F. M. Menger
Department of Chemistry, Emory University, Atlanta, GA 30322
R. Zana
Institut Charles Sadron, 6, rue Boussingault, F67083 Strasbourg Cedex, France
B. Lindman
Chemical Center, University of Lund, Physical Chemistry 1, Lund, Sweden
An amphiphilic compound contains a polar or ionic
group (e.g., a trimethylammonium group) connected to a
long hydrocarbon tail (e.g., a hexadecyl chain). When an
amphiphile is dissolved in water above a certain concentration, it self-assembles into an aggregate of 50100 molecules
called a micelle. Micelles are mentioned in almost all organic chemistry and biochemistry texts owing, in part, to
their importance in detergency and as models of biological
membranes.
Unfortunately, the micelle is most commonly portrayed
in organic chemistry texts (16) and in biochemistry texts
(712) (and, for that matter, in this Journal [13]) as the
spokes of a wheel. Figure 1A is typical of what these drawings look like.
Sometimes, but not often, a picture is described as being schematic; but even with this caveat students receive
a totally erroneous concept of reality. A micelle is, in fact, a
highly disorganized structure with multiple bent chains,
cavities, hydrocarbonwater contact, and deviations from an
exact spherical shape (14). It is thus far better to present a
micelle as a brushheap of molecules (Fig. 1B) than as the
spokes of a wheel. Comparison of the two models, Figure
1A and Figure 1B, reveals clearly one reason why the latter is preferred: one cannot situate 50100 terminal methyl
groups at a single point, namely the center of a sphere. Note
that even Figure 1B is highly schematic in that it is a planar representation of a three-dimensional object. Moreover,
the chains are not drawn with their true van der Waals radii
owing, in part, to the fact that micelle structure is unknown
in such detail. Nonetheless, the Figure 1B does more properly depict the disorder, nonlinearity, and fluctional character of the liquid-like micelle interior.
G. S. Hartley, one of the first to discuss micelle structure, wrote in 1936 the following words (15):
The symmetrical asterisk formhas no physical basis
and is drawn for no other reason than that the human
mind is an organizing instrument and finds unorganized
processes uncongenial.

For reasons of artistic convenience, we presume, the socalled Hartley model evolved into the spokes-of-a-wheel
structure that Hartley disclaimed decades ago. Now that
computer software allows Figure 1B to be drawn as readily
as Figure 1A, textbooks and journals should use this more
appropriate representation.
Editors note: See also the 3-D structure of a micelle depicted
on page 93 of this issue and related discussion on page 94.

Figure 1. A: the misnamed Hartley micelle as portrayed in most

modern chemistry and biochemistry texts. B: a more realistic schematic attempting to depict the disordered and fluid nature of the
micelle interior.

Literature Cited
1. Ouellette, R. J.; Rawn, J. D. Organic Chemistry; Prentice-Hall:
Upper Saddle River, NJ, 1996; p. 792.
2. Morrison, R. T.; Boyd, R. N. Organic Chemistry, 6th ed.; PrenticeHall: Englewood Cliffs, NJ, 1992; p 1125.
3. Wade, L. G. Organic Chemistry, 3rd ed.; Prentice-Hall: Englewood
Cliffs, NJ, 1995; p 1216.
4. Fessenden, R. J.; Fessenden, J. S. Organic Chemistry, 5th ed.;
Brooks/Cole: Pacific Grove, CA, 1994; p 946.
5. Carey, F. A. Organic Chemistry, 2nd ed.; McGraw-Hill: New York,
1992; p 771.
6. Volhardt, K. P. C.; Schore, N. E. Organic Chemistry, 2nd ed.; Freeman: New York, 1994; p 780.
7. Mathews, C. K.; Van Holde, K. E. Biochemistry, 2nd ed.; Benjamin/
Cummings: Menlo Park, CA, 1996; p 321.
8. Horton, H. R.; Moran, L. A.; Ochs, R. S.; Rawn, J. D.; Scrimgeour,
K. G. Principles of Biochemistry, 2nd ed.; Prentice-Hall: Upper
Saddle River, NJ, 1996; p 35.
9. Stryer, L. Biochemistry, 4th ed.; Freeman: New York, 1995; p 269.
10. Voet, D.; Voet, J. G. Biochemistry, 2nd ed.; Wiley: New York, 1995;
p 285.
11. Garrett, R. H.; Grisham, C. M. Biochemistry; Saunders College
Publishing: Fort Worth, TX, 1995; p 39.
12. Lehninger, A. L.; Nelson, D. L.; Cox, M. M. Principles of Biochemistry, 2nd ed.; Worth: New York, 1993; p 87.
13. Goodling, K.; Johnson, K.; Lefkowitz, L.; Williams, B. W. J. Chem.
Educ. 1994, 71, A8.
14. Menger, F. M.; Carnahan, D. W. J. Am. Chem. Soc. 1986, 108, 1297;
Smit, B.; Esselink, K.; Hilbers, P. A. J.; van Os, N. M.; Rupert, L.
A. M.; Szleifer, I. Langmuir 1993, 9, 9; Gruen, D. W. R. J. Phys.
Chem. 1985, 89, 153.
15. Hartley, G. S. Aqueous Solutions of Paraffin-Chain Salts. A Study
of Micelle Formation; Herman: Paris, 1936; see especially Fig. 11A
and the accompanying discussion.

JChemEd.chem.wisc.edu Vol. 75 No. 1 January 1998 Journal of Chemical Education

115