Department of Chemistry, University of Rhode Island, Kingston, RI USA
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1 Supporting Information for Controlled Organocatalytic Ring-Opening Polymerization of - Thionocaprolactone Partha P. Datta and Matthew K. Kiesewetter Department of Chemistry, University of Rhode Island, Kingston, RI USA Figure S1. MALDI-TOF of the PtnCL resulting from the 1/BEMP catalyzed ROP of tncl. Minor peaks could not be identified, but they are not consistent with H+, Li+, Na+ or K+ adducts of cyclic or linear PtnCL with benzyl alcohol or BEMP end groups..
2 Figure S2. (upper) GPC trace of PtnCL resulting from the 1/BEMP catalyzed ROP of tncl from pyrene butanol. The high weight tail grows in late in the ROP. (middle) GPC traces (UV) showing the evolution of the peak shape as a function of conversion. (lower) GPC traces (UV) of the polymer species resulting from allowing the ROP solution to stir with catalysts after full conversion (5h is full conversion).
3 Figure S3. Temperature dependent equilibrium constant for the reversible ROP of tncl catalyzed by TBD from benzyl alcohol. Figure S4. First order evolution of monomer vs time for the copolymerization of tncl and VL. Reaction conditions tncl (1M, 100 mg), VL (1M, 100 mg), 1 mol% benzyl alcohol, 5 mol% BEMP, 5 mol% 1 in C 6D 6.
4 Figure S5. Titration curve for the binding of tncl to 1. Observed chemical shift of 1 (o- protons, 5 mm) vs [tncl] in C 6D 6. Solid line is the fit from the quadratic binding equation. Figure S6. First order evolution of [tncl] vs time in the 1/BEMP catalyzed ROP from benzyl alcohol.
5 Figure S7. The binding of ethyl acetate (or ethyl thionoacetate) to 1 is too low to be measured, and the binding of tncl to 1 is: K eq = 1.6. Because the binding constant of 1 to ethyl thionoacetate is greater than unity, the selectivity of 1 for tncl must be: K eq(sel.) 1.6, or G < 0.27 kcal/mol if the selectivity at the reagents were to be translated to the transition state. This incongruity suggests other modes of action of 1 upon the reaction that are unique to the transition state.
6 Figure S8. 13 C NMR (75 MHz, CDCl 3) spectrum of the polymer resulting from the ROP of tncl (2M, toluene) from benzyl alcohol (1 mol%) catalyzed by DBU (5 mol%) at room temperature. The formation of poly(thionocaprolactone) as evidenced by the carbonyl resonance at 223 ppm.
7 a b b c a Figure S9. 13 C NMR (75 MHz, CDCl 3) spectrum of the polymer resulting from the ROP of tncl (2M, toluene) from benzyl alcohol (1 mol%) catalyzed by DBU (5 mol%) at 100 C results in the formation of poly(thiono-co-thiocaprolactone) as evidenced by the two carbonyl resonances at 223 ppm and 199 ppm. The most downfield resonance is due to unconverted monomer.
8 b b a a Figure S C NMR (75 MHz, CDCl 3) spectrum of P(tnCL-co-VL) (50:50).
9 Figure S11. 1 H NMR (300 MHz, CDCl 3) spectrum of P(tnCL-co-VL) (50:50).
10 Figure S12. 1 H NMR (300 MHz, CDCl 3) spectrum of tncl.
11 Figure S C NMR (75 MHz, CDCl 3) spectrum of tncl.
12 Figure S14. 1 H NMR (300 MHz, CDCl 3) spectrum of PtnCL.
13 COMPUTATIONAL OUTPUT Figure S15. Calculated (DFT B3LYP//6-31G**) electrostatic potential of atoms in the C=X bond of 7-membered and s-trans lactones. methyl thionoacetate SPARTAN '14 Quantum Mechanics Driver: (Win/64b) Release Method: RB3LYP Basis set: 6-31G** Number of shells: 39
14 Number of basis functions: 109 Multiplicity: 1 Solvation: toluene [SM8] Free Energy of Solvation : kj/mol SCF total energy: hartrees Cartesian Coordinates (Angstroms) Atom X Y Z C C C C H H H H H H O O C C H H H H H H S S Atomic Charges: Electrostatic Mulliken Natural 1 C1 : C2 : H1 : H4 : H5 : O2 : C3 : H2 : H6 : H7 : S1 :
15 methyl thionoacetate + TU SPARTAN '14 Quantum Mechanics Driver: (Win/64b) Release Method: RB3LYP Basis set: 6-31G** Number of shells: 184 Number of basis functions: 553 Multiplicity: 1 Solvation: toluene [SM8] Free Energy of Solvation : kj/mol SCF total energy: hartrees 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
16 15 H H H H H H H H H H H H H H H H H H C C C C C C C C C C C C H H H H H H C C C C F F F F F F F F F F F F C C O O C C H H C C H H H H H H H H H H S S Atomic Charges: Electrostatic Mulliken Natural 1 C1 : S1 : N1 : H3 : N2 : H2 : C2 : C3 : C5 :
17 10 C4 : C6 : C7 : H6 : H10 : H7 : H11 : H1 : H5 : H8 : H9 : H12 : H13 : H14 : C8 : C9 : C10 : C11 : C12 : C13 : H4 : H15 : H18 : C14 : C15 : F1 : F2 : F3 : F4 : F5 : F6 : C16 : O2 : C17 : H19 : C18 : H21 : H26 : H28 : H29 : H30 : S2 :
18 methyl acetate Method: RB3LYP Basis set: 6-31G** Number of shells: 38 Number of basis functions: 105 Multiplicity: 1 Solvation: toluene [SM8] Free Energy of Solvation : kj/mol SCF total energy: hartrees Cartesian Coordinates (Angstroms) Atom X Y Z O O C C C C H H H H H H O O C C H H H H H H Atomic Charges: Electrostatic Mulliken Natural 1 O1 : C1 : C2 : H1 : H4 : H5 : O2 : C3 : H2 : H6 : H7 :
19 methyl acetate + TU Method: RB3LYP Basis set: 6-31G** Number of shells: 183 Number of basis functions: 549 Multiplicity: 1 Solvation: toluene [SM8] Free Energy of Solvation : kj/mol SCF total energy: hartrees 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 H H H H
20 18 H H H H H H H H H H H H C C C C C C C C C C C C H H H H H H C C C C F F F F F F F F F F F F O O C C O O C C H H C C H H H H H H H H H H Atomic Charges: Electrostatic Mulliken Natural 1 C1 : S1 : N1 : H3 : N2 : H2 : C2 : C3 : C5 : C4 : C6 : C7 :
21 13 H6 : H10 : H7 : H11 : H1 : H5 : H8 : H9 : H12 : H13 : H14 : C8 : C9 : C10 : C11 : C12 : C13 : H4 : H15 : H18 : C14 : C15 : F1 : F2 : F3 : F4 : F5 : F6 : O1 : C16 : O2 : C17 : H19 : C18 : H21 : H26 : H28 : H29 : H30 :
22 CL Method: RB3LYP Basis set: 6-31G** Number of shells: 62 Number of basis functions: 170 Multiplicity: 1 Solvation: toluene [SM8] Free Energy of Solvation : kj/mol SCF total energy: hartrees Cartesian Coordinates (Angstroms) Atom X Y Z C C O O C C 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 O O Atomic Charges: Electrostatic Mulliken Natural 1 C1 :
23 2 O1 : C2 : H1 : H3 : C3 : H4 : H5 : C4 : H2 : H8 : C5 : H6 : H10 : C6 : H9 : H12 : O2 : CL + TU Method: RB3LYP Basis set: 6-31G** Number of shells: 207 Number of basis functions: 614 Multiplicity: 1
24 Solvation: toluene [SM8] Free Energy of Solvation : kj/mol SCF total energy: hartrees Cartesian Coordinates (Angstroms) Atom X Y Z C C O O C C 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 H H N N C C 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
25 41 H H H H H H H H H H H H H H H H S S C C C C F F F F F F F F F F F F O O Atomic Charges: Electrostatic Mulliken Natural 1 C1 : O1 : C2 : H1 : H3 : C3 : H4 : H5 : C4 : H2 : H8 : C5 : H6 : H10 : C6 : H9 : H12 : H7 : N1 : C7 : N2 : H15 : C8 : C9 : C10 : C11 : C12 : C13 :
26 29 H14 : H16 : H19 : C14 : C15 : C16 : C17 : C18 : C19 : H13 : H20 : H21 : H22 : H23 : H24 : H25 : H26 : H27 : H28 : H29 : S2 : C20 : C21 : F1 : F2 : F3 : F4 : F5 : F6 : O2 : tncl Method: RB3LYP Basis set: 6-31G** Number of shells: 63 Number of basis functions: 174 Multiplicity: 1
27 Solvation: toluene [SM8] Free Energy of Solvation : kj/mol SCF total energy: hartrees Cartesian Coordinates (Angstroms) Atom X Y Z S S C C O O C C 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 Atomic Charges: Electrostatic Mulliken Natural 1 S1 : C1 : O1 : C2 : H1 : H3 : C3 : H4 : H5 : C4 : H2 : H8 : C5 : H6 : H10 : C6 : H9 : H12 :
28 tncl + TU Method: RB3LYP Basis set: 6-31G** Number of shells: 208 Number of basis functions: 618 Multiplicity: 1 Solvation: toluene [SM8] Free Energy of Solvation : kj/mol SCF total energy: hartrees Cartesian Coordinates (Angstroms) Atom X Y Z S S C C O O C C 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
29 18 H H H H N N C C 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 S S C C C C F F F F F F F F F F F F Atomic Charges: Electrostatic Mulliken Natural 1 S1 : C1 : O1 : C2 : H1 :
30 6 H3 : C3 : H4 : H5 : C4 : H2 : H8 : C5 : H6 : H10 : C6 : H9 : H12 : H7 : N1 : C7 : N2 : H15 : C8 : C9 : C10 : C11 : C12 : C13 : H14 : H16 : H19 : C14 : C15 : C16 : C17 : C18 : C19 : H13 : H20 : H21 : H22 : H23 : H24 : H25 : H26 : H27 : H28 : H29 : S2 : C20 : C21 : F1 : F2 :
31 55 F3 : F4 : F5 : F6 : tcl Method: RB3LYP Basis set: 6-31G** Number of shells: 63 Number of basis functions: 174 Multiplicity: 1 Solvation: toluene [SM8] Free Energy of Solvation : kj/mol SCF total energy: hartrees Cartesian Coordinates (Angstroms) Atom X Y Z O O C C S S C C 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
32 18 H H Atomic Charges: Electrostatic Mulliken Natural 1 O1 : C1 : S1 : C2 : H1 : H3 : C3 : H5 : H6 : C4 : H4 : H7 : C5 : H8 : H9 : C6 : H2 : H11 : tcl + TU Method: RB3LYP Basis set: 6-31G** Number of shells: 208 Number of basis functions: 618 Multiplicity: 1 Solvation: toluene [SM8]
33 Free Energy of Solvation : kj/mol SCF total energy: hartrees Cartesian Coordinates (Angstroms) Atom X Y Z C C H H N N H H C C S S N N H H O O C C S S C C 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 C C 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 C C
34 43 C C C C C C C C C C H H H H H H C C C C F F F F F F F F F F F F Atomic Charges: Electrostatic Mulliken Natural 1 C1 : H2 : N1 : H3 : C2 : S1 : N2 : H5 : O1 : C4 : S2 : C5 : H10 : H11 : C6 : H13 : H14 : C7 : H15 : H16 : C8 : H9 : H18 : C9 : H17 : H19 : C10 : H1 : H12 : C11 :
35 31 H21 : H22 : C12 : H4 : H24 : C13 : H23 : H26 : C14 : H25 : H28 : C3 : C15 : C16 : C17 : C18 : C19 : H6 : H7 : H27 : C20 : C21 : F1 : F2 : F3 : F4 : F5 : F6 :
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