Abstract
The occurrence of a nanoscale disperse phase in the homochiral solutions of N-trifluoroacetylated α-amino alcohols (TFAAAs) was found experimentally by the observation of the Tyndall effect and dynamic light scattering (DLS) measurements. The nanoscale fraction was observed at concentrations lower than the critical concentration of gelation and string formation (c*). Direct optical microscopy showed that, as a rule, strings with a helical structure resulted from the homogeneous nucleations. Chirooptical measurements revealed some signs of helicity below the concentration threshold (c*). The molecular dynamics simulation of the condensation of a homochiral TFAAA in heptane showed that TFAAA molecular aggregates 2–3 nm in diameter were formed already after 100 ns. These aggregates have some signs of the homogeneous nucleations with a helical structure, and they can be considered as the nuclei of helical strings.
Similar content being viewed by others
References
G. Godeau and D. Barthelemy, Langmuir 25, 8447 (2009).
M. George and R. G. Weiss, Accounts Chem. Res. 39, 489 (2006).
A. A. Bredikhin, Z. A. Bredikhina, and A. V. Pashagin, Mendeleev Commun. 21, 144 (2011).
C. Li, N. J. Buurma, I. Haq, C. Turner, and S. P. Armes, Langmuir 21, 11026 (2005).
J. Peng, K. Liu, J. Liu, et al., Langmuir 24, 2992 (2008).
A. Gansäuer, I. Winkler, T. Klawonn, et al., Organometallics 28, 1377 (2008).
A. R. Hirst, I. A. Coates, T. R. Boucheteau, et al., J. Am. Chem. Soc. 130, 9113 (2008).
C. C. Lee, C. Grenier, E. W. Meijer, and A. P. H. J. Schenning, Chem. Soc. Rev. 38, 671 (2009).
S. Vauthey, S. Santoso, H. Gong, et al., Proc. Natl. Acad. Sci. 99, 5355 (2002).
M. George, G. P. Funkhouser, P. Terech, and R. G. Wise, Langmuir 22, 7885 (2006).
S. Laan, B. L. Feringa, R. M. Kellogg, and J. Esch, Langmuir 18, 7136 (2002).
K. Inoue, Y. Ono, Y. Kanekiyo, et al., J. Org. Chem. 64, 2933 (1999).
B. G. Bag, G. C. Maity, and S. R. Pramanik, Supramol. Chem. 17, 383 (2010).
J. Madsen, S. P. Armes, K. Bertal, et al., Biomacromolecules 10, 1875 (2009).
C. Zhan, P. Gao, and M. Liu, Chem. Commun., 462 (2005).
P. Terech and R. G. Weiss, Chem. Rev. 97, 3133 (1997).
S. J. Langford, M. J. Latter, V. L. Lau, et al., Org. Lett. 8, 1371 (2006).
R. G. Weiss and P. Terech, Molecular Gels (Springer, Dordecht, 2006).
P.-G. de Gennes, Scaling Concepts in Polymer Phyics (Cornell Univ. Press, Ithaca, London, 1979).
S. V. Stovbun, Russ. J. Phys. Chem. B 5, 546 (2011).
S. V. Stovbun, O. N. Krutius, A. M. Zanin, D. S. Skorobogat’ko, and R. G. Kostyanovskii, Russ. J. Phys. Chem. B 5, 846 (2011).
S. V. Stovbun, A. M. Zanin, A. A. Skoblin, A. I. Mikhailov, R. G. Kostyanovskii, M. V. Grishin, and B. R. Shub, Russ. J. Phys. Chem. B 5, 1019 (2011).
S. V. Stovbun and A. A. Skoblin, Mosc. Univ. Phys. Bull. 67, 317 (2012).
S. V. Stovbun, A. M. Zanin, A. A. Skoblin, A. I. Mikhailov, and A. A. Berlin, Dokl. Phys. Chem. 442, 36 (2012).
S. V. Stovbun, A. M. Zanin, A. A. Skoblin, D. P. Shashkin, A. I. Mikhailov, M. V. Grishin, and B. R. Shub, Russ. J. Phys. Chem. B 7, 1 (2013).
S. V. Stovbun, A. A. Skoblin, A. M. Zanin, M. V. Grishin, B. R. Shub, Yu. M. Rybin, I. M. Ageev, G. G. Shishkin, and V. A. Tverdislov, Bull. Exp. Biol. Med. 154, 34 (2012).
S. V. Stovbun and A. A. Skoblin, Mosc. Univ. Phys. Bull. 67, 274 (2012).
S. V. Stovbun, A. A. Skoblin, and V. A. Tverdislov, Bull. Exp. Biol. Med. 152, 703 (2012).
S. V. Stovbun, A. M. Zanin, D. S. Skorobogat’ko, A. A. Skoblin, Ya. A. Litvin, A. I. Mikhailov, O. N. Krutius, and R. G. Kostyanovskii, Russ. J. Phys. Chem. B 6, 341 (2012).
S. V. Stovbun and A. A. Skoblin, Khim. Fiz. 31 (7), 7 (2012).
S. V. Stovbun and A. A. Skoblin, Mosc. Univ. Phys. Bull. 67, 278 (2012).
S. V. Stovbun, A. A. Skoblin, J. A. Litvin, M. G. Mikhaleva, and V. A. Tverdislov, Mosc. Univ. Phys. Bull. 70, 45 (2015).
V. A. Tverdislov and L. V. Yakovenko, Mosc. Univ. Phys. Bull. 63, 151 (2008).
V. A. Tverdislov, A. E. Sidorova, and L. V. Yakovenko, Biophysics 57, 120 (2012).
V. A. Tverdislov, Biophysics 58, 128 (2013).
S. V. Stovbun, A. A. Skoblin, and V. A. Tverdislov, Biophysics 59, 876 (2014).
I. I. Artobolevsky, Theory of Mechanisms and Machines. (Textbook. 4th ed., M.: Nauka, 1988).
S. V. Stovbun, A. A. Skoblin, Y. A. Litvin, A. A. Kirsankin, M. V. Grishin, B. R. Shub, Y. V. Zubavichus, A. A. Veligzhanin, L. D. Popov, E. A. Raspopova, and Y. N. Tkachenko, Russ. J. Phys. Chem. B 8, 801 (2014).
S. V. Stovbun, A. A. Skoblin, A. M. Zanin, Ya. A. Litvin, V. A. Tverdislov, A. A. Kirsankin, M. V. Grishin, and B. R. Shub, Russ. J. Phys. Chem. B 8, 620 (2014).
S. Stovbun, A. Skoblin, A. Zanin, F. Bulygin, V. Fedorenko, and V. Lyaskovskiy, Khim. Fiz. 32 (3), 12 (2013).
S. V. Stovbun, A. M. Zanin, A. A. Skoblin, I. A. Bilenko, F. V. Bulygin, O. E. Dracheva, V. S. Fedorenko, and V. L. Lyaskovskii, Meas. Tech. 55, 734 (2012).
D. V. Zlenko, M. G. Mikhaleva, and S. V. Stovbun, Russ. J. Phys. Chem. B 10, 531 (2016).
R. G. Kostyanovsky, D. F. Lenev, O. N. Krutius, and A. A. Stankevich, Mendeleev Commun. 15, 140 (2005).
D. A. Friedrichsberg, Course of Colloid Chemistry (St. Petersburg: Lan, 2010).
B. Hess, D. Spoel, and E. Lindahl, GROMACS User Manual 4.5 (The GROMACS Development Teams at the Royal Inst. Technol., Uppsala Univ., Sweden, 2001–2010).
B. Hess, C. Kutzner, D. Spoel, and E. Lindahl, J. Chem. Theory Comput. 4, 435 (2008).
W. L. Jorgensen, D. S. Maxwell, and J. Tirado-Rives, J. Am. Chem. Soc. 118, 11225 (1996).
P. B. Moore, C. F. Lopez, and M. L. Klein, Biophys. J. 81, 2484 (2001).
H. J. C. Berendsen, J. P. M. Postma, A. di Nola, and J. R. Haak, Phys. Rev. 31, 1695 (1985).
V. L. Golo and K. V. Shaitan, Biophysics 47, 611 (2002).
U. Essmann, L. Perera, M. L. Berkowitz, et al., J. Chem. Phys. 103, 8577 (1995).
C. I. Bayly, P. Cieplak, W. D. Cornell, and P. A. Kollman, J. Phys. Chem. 97, 10269 (1993).
A. A. Granovsky, Firefly version 7.1.G. http://classic.chem.msu.su/gran/firefly/index.html.
S. Pronk, S. Páll, R. Schulz, et al., Bioinformatics 29, 845 (2013).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.M. Zanin, D.V. Zlenko, Ya.A. Litvin, A.A. Skoblin, S.V. Stovbun, 2018, published in Khimicheskaya Fizika, 2018, Vol. 37, No. 6, pp. 9–17.
Rights and permissions
About this article
Cite this article
Zanin, A.M., Zlenko, D.V., Litvin, Y.A. et al. Helical Structure of Nucleation in a Solution of a Chiral Trifluoroacetylated Amino Alcohol. Russ. J. Phys. Chem. B 12, 394–402 (2018). https://doi.org/10.1134/S1990793118030326
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1990793118030326