Features of self-organization of highly dilute solutions of (S)-, (R)-, and (SR)-methionines and related carbamides and glycolurils

• Published in: Russian chemical bulletin 2015-09, Vol.64 (9), p.2125-2134
• Main Authors: Ryzhkina, I. S., Sergeeva, S. Yu, Masagutova, E. M., Murtazina, L. I., Mishina, O. A., Timosheva, A. P., Baranov, V. V., Kravchenko, A. N., Konovalov, A. I.
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Full Articles; Inorganic Chemistry; Organic Chemistry
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-015-1127-8

Aqueous solutions of ( S )-, ( R )-, and ( SR )-methionines ( 1–3 ); carbamide ( 4 ); ( S )-, ( R )-, and ( SR )- N -carbamoylmethionines ( 5–7 ); glycoluril ( 8 ); and glycolurils containing ( S )and ( R )-methionine moieties ( 9 and 10 ) kept under natural and hypoelectromagnetic conditions were studied in comparison by a complex of physicochemical methods (dynamic and electrophoretic light scattering, conductometry, pH-metry, and dielcometry). The process of selforganization and the properties of dilute solutions (1.0•10 –15 –10 –1 mol L –1 ) of compounds 1 – 10 was shown for the first time to depend substantially on the structure of the solute and configuration of methionine (Met) enantiomers. In the series 1 – 3 , the greatest ability to self-organization is observed for solutions of (SR)-Met in which supramolecular domains (1.0•10 –5 –1.0•10 –1 mol L –1 ) and nanoassociates (1.0•10 –11 –1.0•10 –8 mol L –1 ) are formed. The formation of nanoassociates in a concentration range of 1.0•10 –12 –1.0•10 –6 mol L –1 can be responsible for the appearance of nonmonotonic concentration dependences of the physicochemical properties of solutions of N-carbamoylmethionines 5 – 7 , whereas the physicochemical properties are more pronounced in solution of (S)-N-carbamoylmethionine 5 than in solutions of 6 and 7 . The strongest influence of the configuration of the Met enantiomer on the ability of solution to self-organization was revealed in a series of glycolurils 9 , 10 : solutions of 9 with the (S)-Met moiety are disperse systems in which nanoassociates are formed in a range of 1.0•10 –15 –1.0•10 –5 mol L –1 , whereas in solutions of 10 with the ( R )-Met fragment the ability to self-organization in the low-concentration range is absent.