Cocatalyst Binding Effects in Organocatalytic Ring- Opening Polymerization of L-Lactide
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1 University of Rhode Island Chemistry Faculty Publications Chemistry 2015 Cocatalyst Binding Effects in Organocatalytic Ring- Opening Polymerization of L-Lactide Oleg I. Kazakov Matthew K. Kiesewetter University of Rhode Island, Follow this and additional works at: The University of Rhode Island Faculty have made this article openly available. Please let us know how Open Access to this research benefits you. This is a pre-publication author manuscript of the final, published article. Terms of Use This article is made available under the terms and conditions applicable towards Open Access Policy Articles, as set forth in our Terms of Use. Citation/Publisher Attribution Kazakov, O. I., & Kiesewetter, M. K. (2015). Cocatalyst Binding Effects in Organocatalytic Ring-Opening Polymerization of L- Lactide. Macromolecules, 48(17), Available at: This Article is brought to you for free and open access by the Chemistry at DigitalCommons@URI. It has been accepted for inclusion in Chemistry Faculty Publications by an authorized administrator of DigitalCommons@URI. For more information, please contact digitalcommons@etal.uri.edu.
2 ln([l-la] 0 /[L-LA]) ln([la] 0 /[LA]) Supporting Information for Cocatalyst Binding Effects in Organocatalytic Ring-Opening Polymerization of L-Lactide Oleg I. Kazakov and Matthew K. Kiesewetter* Department of Chemistry, University of Rhode Island, Kingston, RI USA y = x R² = t, h Figure S1. First order evolution of [LA] versus time in the 1/HMTETA catalyzed ROP of LA from benzyl alcohol in CDCl3. [LA]o = 0.5 mmol; [HMTETA]o = [1]o = mmol; [benzyl alcohol]o = mmol y = x R² = t, h Figure S2. First order evolution of [LA] versus time in the 1/Me6TREN catalyzed ROP of LA from benzyl alcohol in CDCl3. [LA]o = 0.5 mmol; [Me6TREN]o = [1]o = mmol; [benzyl alcohol]o = mmol.
3 ln([l-la] 0 /[L-LA]) y = x R² = t, h Figure S3. First order evolution of [LA] versus time in the 1/TMEDA catalyzed ROP of LA from benzyl alcohol in CDCl3. [LA]o = 0.5 mmol; [TMEDA]o = [1]o = mmol; [benzyl alcohol]o = mmol k obs, h y = x R² = A) ([1]+[TMEDA]), M
4 k obs, h y = x - 1E-05 R² = B) [1], M k obs, h [TMEDA], M C) Figure S4. Observed rate constant (kobs) vs concentration plots for the 1/TMEDA catalyzed ROP of L-LA: A) [1] = [TMEDA], B) [1] > [TMEDA], [TMEDA] = 0.05 M, C) kobs vs [TMEDA], [1] = 0.05 M (bottom).
5 δ, ppm Figure S5. (left) Observed rate constant (kobs) vs [1][Me6TREN], and (right) observed rate constant (kobs) vs [1] 2 for the 1/Me6TREN catalyzed ROP of L-LA /DABCO 1/Me6TREN 1/PMDTA 1/TMEDA 1/TMTACN [Alkyl Amine], M Figure S6. Binding curves for the association of 1 with alkylamine cocatalysts. The curve fitting method was used to extract binding constants, see Experimental Section. The chemical shift is of the ortho-protons of 1. Equation used for binding studies. 1-3 obs = H ( /2[H]o){[H]o + [G]o + 1/K (([H]o + [G]o + 1/K) 2 4[H]o[G]o) 1/2 } Where: obs is the observed chemical shift of the TU in the presence of base H is the chemical shift of free TU in the absence of base is the difference in the chemical shift of host and complex, ( C H) K is the binding constant, Keq The binding constants were determined by fitting the binding curve with the quadratic form of the binding equation shown above (Keq and variables). 1-2 The value of the binding constants determined from curve fitting are within experimental error of those
6 Ln (Keq) determined from the slope of the linear (Lineweaver-Burke) forms of the binding equation /T (1/K) HMTETA Me6TREN TACN TMEDA DABCO PMDETA Figure S7. Temperature dependent binding. Computational Images of Cocatalyst Complexes. Figure S TMEDA. See Experimental Section for computational details and below for optimized coordinates.
7 Figure S Me6TREN. See Experimental Section for computational details and below for optimized coordinates. Figure S DABCO. See Experimental Section for computational details and below for optimized coordinates.
8 Figure S HMTETA. See Experimental Section for computational details and below for optimized coordinates. Optimized Energies and Atomic Coordinates: 1 + HMTETA Cartesian Coordinates (Angstroms) Atom X Y Z C C S S N N H H N N H H C C C C C C C C C C C C H H H H H H C C C C C C C C C C C C H H H H H H
9 25 H H H H H H H H H H H H H H H H C C C C F F F F F F F F F F F F N N C C H H H H C C C C H H H H C C H H H H C C H H H H N N N N C C H H H H H H C C H H H H H H C C H H H H C C H H H H H H H H H H H H C C H H H H N N C C H H H H H H C C
10 84 H H H H H H TACN Cartesian Coordinates (Angstroms) Atom X Y Z N N C C H H H H H H C C H H H H C C H H H H C C H H H H C C H H H H N N N N C C H H H H C C H H H H C C H H H H H H C C N N H H N N H H S S C C C C C C C C C C C C H H H H H H C C C C C C C C C C
11 50 C C H H H H H H H H H H H H H H H H H H H H H H C C C C F F F F F F F F F F F F C C H H H H H H Me 6TREN Cartesian Coordinates (Angstroms) Atom X Y Z C C S S N N H H N N H H C C C C C C C C C C C C H H H H H H C C C C C C C C C C C C H H H H H H H H H H H H
12 28 H H H H H H H H H H C C C C F F F F F F F F F F F F N N C C H H H H C C C C H H H H C C H H H H C C H H H H C C H H H H N N N N N N C C H H H H H H C C H H H H H H C C H H H H H H C C H H H H H H C C H H H H H H C C H H H H H H H H H H
13 1 + DABCO Cartesian Coordinates (Angstroms) Atom X Y Z C C S S N N H H N N H H C C C C C C C C C C C C H H H H H H C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H C C C C F F F F F F F F F F F F N N C C H H H H C C H H H H C C H H H H
14 51 C C H H H H C C H H H H C C H H H H N N PMDETA Cartesian Coordinates (Angstroms) Atom X Y Z C C S S N N H H N N H H C C C C C C C C C C C C H H H H H H C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H C C C C F F F F F F F F F F F F N N
15 42 C C H H H H C C C C H H H H C C H H H H C C H H H H N N N N C C H H H H H H C C H H H H H H C C H H H H H H C C H H H H H H H H H H H H TMEDA Cartesian Coordinates (Angstroms) Atom X Y Z C C S S N N H H N N H H C C C C C C C C C C C C H H H H H H C C C C
16 18 C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H C C C C F F F F F F F F F F F F N N C C H H H H C C C C H H H H C C H H H H N N C C H H H H H H C C H H H H H H H H H H H H H H SI References (1) Webb, J. E. A.; Crossley, M. J.; Turner, P.; Thordarson, P. J. Am. Chem. Soc. 2007, 129, (2) Thordarson, P. Chem. Soc. Rev. 2011, 40, (3) Deranleau, D. A. J. Am. Chem. Soc. 1969, 91, 4044.
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