Supporting Information: Design principles for α-tocopherol analogues

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1 Supplementary Material for Organic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2005 Supporting Information: Design principles for α-tocopherol analogues David Shanks,* a Håkan Frisell, b Henrik Ottosson, a and Lars Engman* a a Department of Chemistry, Organic Chemistry, Box 599, Uppsala University, SE Uppsala, Sweden; lars.engman@kemi.uu.se b Department of Organic Chemistry, Karlstad University, SE Karlstad, Sweden. Contents i. Tables of calculated vs experimental IP and BDE values for reference compounds. S1 ii. Geometrical parameters and BDE values for compounds 4-7. S2 iii. Absolute energies, energy corrections and cartesian coordinates for compounds 4-6. S3-S12 i. Table of calculated vs experimental IP values for reference compounds. compound calculated IP / ev Experimental IP / ev Median Lowest Highest 4-methoxyphenol methoxytoluene dimethyl telluride thioanisole hydroquinone methoxythiophene anisole methylphenol benzo[b]thiophene methylthiophene phenol tellurophene benzenethiol Benzo[b]furan methylfuran methylselenophene tetrahydrothiophene acetylselenophene selenophene thiophene furan acetylfuran tetrahydrofuran ethyl 4-methylphenyl selenide ,2-Dimethyl-2,3-dihydrobenzo[b]selenophene (methylthio)tellurophene ethyl phenyl selenide methyl 2-methylphenyl selenide benzo[b]tellurophene (methylthio)selenophene selenoanisole (methylthio)thiophene benzo[b]selenophene methyltellurophene benzeneselenol S1

2 resorcinol acetyltellurophene acetylthiophene Table of calculated vs experimental BDE values for reference compounds Phenol Calc. BDE / kcal mol -1 Exp. BDE / kcal mol -1 unsubstituted methyl t-butyl methoxy ,6-dimethyl ,6-dimethoxy ,5-di-t-butyl ,5-dimethoxy ,4,6-trimethyl ,4,6-trimethoxy ,3,6-trimethyl-4- methoxy- 2,3,5,6-tetramethyl-4- methoxy a ii. Geometrical parameters and BDE values for compounds 4-7 a-d. a Compound dihedral φ / bonding angle σ / sum of aromatic angles λ / BDE / kcal mol -1 4a a a a b b b b c c c c d d d d a BDE values given relative to the calculated value for HPMC (6a). S2

3 iii. Absolute energies (a.u.), energy corrections (a.u.) and cartesian coordinates for compounds a antioxidant E(RB+HF-LYP) = (LANL2DZ) E(RB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= a phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= a radical cation E(UB+HF-LYP) = Zero-point correction= b antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= S3

4 4b phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= b radical cation E(UB+HF-LYP) = Zero-point correction= c antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= c phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= c radical cation E(UB+HF-LYP) = Zero-point correction= S4

5 d antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= d phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= d radical cation E(UB+HF-LYP) = Zero-point correction= a antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= S5

6 a phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= a radical cation E(UB+HF-LYP) = Zero-point correction= b antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= b phenoxyl radical S6

7 E(ROB+HF-LYP) = Thermal correction to Enthalpy= b radical cation E(UB+HF-LYP) = Zero-point correction= c antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= c phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= S7

8 c radical cation E(UB+HF-LYP) = Zero-point correction= d antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= d phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= d radical cation E(UB+HF-LYP) = Zero-point correction= S8

9 a antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= a phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= a radical cation E(UB+HF-LYP) = Zero-point correction= b antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= S9

10 b phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= b radical cation E(UB+HF-LYP) = Zero-point correction= c antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= S10

11 c phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= c radical cation E(UB+HF-LYP) = Zero-point correction= d antioxidant E(RB+HF-LYP) = (LANL2DZ) E(ROB+HF-LYP) = (LANL2DZdp) Zero-point correction= Thermal correction to Enthalpy= d phenoxyl radical E(ROB+HF-LYP) = Thermal correction to Enthalpy= S11

12 d radical cation E(UB+HF-LYP) = Zero-point correction= S12

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