Supporting Information for Achieving Accurate. Reduction Potential Predictions for. Anthraquinones in Water and Aprotic Solvents:
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1 Supporting Information for Achieving Accurate Reduction Potential Predictions for Anthraquinones in Water and Aprotic Solvents: Effects of Inter- and Intramolecular H-Bonding and Ion Pairing Hyungjun Kim, Theodore Goodson, III, and Paul M. Zimmerman Department of Chemistry, Ann Arbor, Michigan 48109, United States Phone: (734) Contents: 1. Figure S1. Structure of AQs in acidic aqueous solution and corresponding short name. 2. Table S1. Theoretical and experimental two-electron two-proton reduction potential of AQs in QW set. (in V) 3. Table S2. The calculated first and second reduction potential (RP) of anthraquinone in the library. (in V) 4. Table S3. The calculated first and second reduction potential of selected five AQs depending on the chemical models. (in V) 5. Table S4. The first reduction potential at different local minima (w/ and w/o H-bond), and numerical value of each interaction. (in V) To whom correspondence should be addressed 1
2 Figure S1. Structure of AQs in acidic aqueous solution and corresponding short name. S 3 H S 3 H S 3 H S 3 H QW-1 QW-2 QW-3 S 3 H S 3 H S 3 HH 3 S S 3 H H 3 S QW-4 QW-5 QW-6 H C 2 H C 2 Me H QW-7 QW-8 QW-9 H QW-10 QW-11 QW-12 NH 2 NH 2 QW-13 QW-14 QW-15 S2
3 Figure S1. Continued. NH 2 NH 2 NH 2 H QW-16 QW-17 QW-18 H H 3 S S 3 H QW-19 S3
4 Table S1. Theoretical and experimental two-electron two-proton reduction potential of AQs in QW set. (in V) QW-n R1 R2 R3 R4 R5 R6 R7 R8 DFT(PCM) a DFT(SM8) b QM/MM c Expt. 1 S3H d 2 - S3H d 3 S3H S3H d 4 S3H S3H d 5 - S3H S3H d 6 - S3H S3H d 7 - C2H d 8 - C2Me d 9 H H e 10 H - - i f 11 Me - - i f 12 Me - - Me f 13 i - - i f 14 NH g 15 - NH g 16 NH2 Et g 17 NH2 Me Me g 18 NH2 Me - Me g 19 H S3H S3H H h [a] ωb97x-d/g3large/pcm(bondi)/ωb97x-d/6-31g* [b] QM: Anthraquinone derivatives, MM: Water. QM(ωB97X-D/G3large)/MM(TIP3P) [c] ωb97x-d/6-31+g**/sm8/ωb97x-d/6-31g* [d] Conant, J. B., Fieser, L. F., J. Am. Chem. Soc., 1924, 46, [e] jani, R., Raouf, J. Ebrahimi, M., Iran. J. Chem. & Chem. Eng., 2001, 20, [f] Salimi, A., Mousavi, M. F., Sharghi, H., Shamsipur, M., Bull. Chem. Soc. Jpn., 1999, 72, [g] Shamsipur, M., Salimi, A., Golabi, S. M., Sharghim H., Mousavi, M. F., J. Solid State Electrochem., 2001, 5, [h] Huskinson, B., Marshak, M. P., Suh, C., Er. S., Gerhardt, M. R., Galvin C. J., Chen, X., Aspuru-Guzik, A., Gordon, R. G., Aziz, M. Nature, 2014, 505, [i] CH2CHCH2 S4
5 Table S2. The calculated first and second reduction potential (RP) of anthraquinone in the library. (in V) CF a tbu tbu tbu Acetyl CH2Br [i] 8 - CH2Cl [i] 9 - CH2H Cl Cl CHBr [i] 12 - Cl Cl Cl Me Cl N C2H C2H Cl C2H C2H C2H NH CCl Et Me Me Me NH NH NH2 Cl H H H NH Me Me S3H S3H S3H S3H S3H S5
6 Table S2. Continued. 31 b b [ii] 32 b b [ii] 33 b - - b [iii] [iii] 34 c c [iii] 35 d d [iv] 36 e e f g h j k - CH2Me - - CH2Me - CH2Me l - - l Allyloxy Allyloxy - CH2Me Allyloxy - Me Br - - NHMe Cl Cl Cl Cl Cl Cl - - Cl Cl - - Cl Cl - - Cl Cl CCl [i] 53 Cl C2H Cl Me F F F F F F F F Me - - Me Me Me NEt2 - - NEt NH i Pr NH i Pr S3H [ii] [ii] S6
7 Table S2. Continued. 61 NH i Pr - - Br NH i Pr - - Br S3H [ii] 63 NH i Pr - - NH i Pr NH NH NH NH Cl - - Cl NH NH NH NHCφ m NH S3H [ii] [ii] 70 NH2 - - Cl NH2 - - C2H [v] 72 NH2 - - NH NH2 - - NH2 - S3H NH2 - - NH2 NH2 - - NH NH2 - - NH2 N NH2 - - NHCφ NH2 - - NHMe NH2 - - N2 NH2 - - N NH2 - - H NH2 - - H Cl - - Cl NH2 - Br H NH2 n n NH NH2 Br - o [iii] 84 NH2 Br - q NH2 Br - Br NH2 Br - NH2 N NH2 Br - NHφ NH2 Br - H NH2 CH=Nφ - NHCφ NH2 CH S7
8 Table S2. Continued. 91 NH2 Cl - r NH2 Cl - Br NH2 Cl - Cl NH2 Cl Cl NH NH2 CN - NHC6H11 s NH2 CN CN NH NH2 C2Et - NH NH2 C2H NH2 C2H - N NH2 Me NH2 Me - Br NH2 Me - Cl NH2 NH NH2 NHCφ - Br NH2 NHMe NH2 N2 - NH NH2 (CH2)2H - H NH2 φ - H NH2 φ φ NH NH2 Me - H NH2 S(CH2)2H - NHφ NH2 Sφ - H NH2 SH S3H NH2 SH - NH NH2 S3H NH2 S3H S3H [ii] 117 NH2 S3H S3H NH2 S3H S3H NH2 S3H - - S3H [ii] 120 NH2 S3H - o S8
9 Table S2. Continued. 121 NH2 S3H - u NH2 S3H - w NH2 S3H - x NH2 S3H - Br NH2 S3H - NH NH2 S3H - NHφ NH2 S3H - NHC6H11 s NH2 S3H - NHMe NHC6H11 s NHC6H11 s S3H [ii] [ii] 131 NHC6H11 s - - Br NHCφ [iii] 133 NHCφ NHCφ NHCφ Cl NHCφ NHCφ NHCφ - - Cl [iii] 137 NHCφ - - NHCφ NHCφ - - H NHCφ NHMe NHMe - - y NHMe - - z NHMe - - Br NHMe Br - Br NMe2 - - NMe N N N N S3H [ii] 148 N N N S3H [ii] 150 N2 C2H S9
10 Table S2. Continued. 151 N2 Me φ φ φ φ CH2Me - CH2Me - CH2Me - CH2Me H Me [vi] 156 H H H r - - r H NH i Pr [vi] 159 H NH i Pr - - Br H H [vi] 161 H - - aa H - - NHCφ H - - r H - - NH2 NH2 - - H H - - NH2 H - - NH H - - NHφ N2 - - H H - - NHMe H - - N H - - N2 N2 - - H H - - N2 H - - N [vi] 170 H - - N2 Sφ - - H H - - H H - - H Cl - - Cl H - - H NH H - - H NHφ - - NHφ H - - H N H - - H H H - - H H - - H H - ab NH2 H - - NH H - CH2H H [vi] 180 H - Me [vi] S10
11 Table S2. Continued. 181 H - Me H H - H - - Me - H H - H NH H - Me - - Me - H H ab - NH2 H - - NH H ab - N2 H - - N [vi] 187 H ac [vi] 188 H ac Me [vi] 189 H Allyl [vi] 190 H Br - H H CH2φ - H H CH2Br CH2Br H [i] 193 H Me Me [vi] 194 H NHBu - H H H [vi] 196 H H - - H - - H H H - H H H NH [vi] 199 H H S3H H S(CH2)2H - H H Sφ - H H S3H S3H H [ii] 203 H S3H - - H S3H [ii] 204 H S3H - NH2 NH2 - S3H H [ii] 205 H S3H - NH2 N2 - S3H H [ii] 206 H S3H - NH2 H - - NH [ii] 207 H S3H - NH2 H S3H - NH [ii] 208 H S3H - NH2 H S3H - N [ii] 209 H S3H - H [ii] 210 Me Me S11
12 Table S2. Continued. 211 Me - - r Me ad Me Acetyl Me Allyl Me Me Me Me Pentyl Me SBr [i] [i] 218 S3H [ii] 219 S3H S3H [ii] [ii] 220 S3H S3H [ii] 221 S3H C2H [ii] [ii] Functional group: If not specified, there ia a hydrogen atom. a) Piperidin-1-yl, b) p-toluidino-2 -sulfonic acid, c) 2-Nitrophenylamino, d) 2,4-Dinitrophenoxy, e) Phenylethylamino, f ) N=N-C6H4NMe2, g) 3-Methoxyphenoxy, h) NH(CH2)3Me, i) Prefix, iso, j) 1,3-Dioxolan-2-yl, k) Hexa-2,5-dienyloxy, l) 2-(4-Hydroxyphenyl)ethylamino m) φ: phenyl ring, n) Ethoxyphenoxy, o) 4-Methylphenylsulfonicamido, p) Prefix, para, q) NH(CH2)NMe2, r) p-toluidino, s) Cyclohexyl, t) Prefix, tert, u) p-methylaminomethylanilino, w) 2,4-Eiethyl-6-methylphenylamino, x) 4-Acetylaminoanilino, y) NH(CH2)2H, z) NH(CH2)4NMe2, aa) p-methoxybenzoylamino, ab) p-methoxyphenyl, ac) CH2CH=CHCH2CH3, ad) CH=CH-(CH2)2-CH3 Reduction potential [i] Reductive dehalogenation in gas phase geometry optimization. Solution-phase geometry optimization is performed. If reductive dehalogenation is observed at solution-phase geometry also, this is left blank. [ii] C= Protonation by S3H [iii] C= Protonation by NH or NH2 [iv] Ring formation [v] C= Protonation C2H [vi] C= Protonation H S12
13 Table S3. The calculated first and second reduction potential of selected five AQs depending on the chemical models. (in V) 1 st reduction potential 2 nd reduction potential Solute-only with PCM Solute-only with SM8 Expt. a Solute-only with PCM Solute-only with SM8 IP-corrected in gas IP-corrected in sol Expt. a a) Experimental results are from our measurements. The SM8 model gives improved estimation for the second reduction of the Solute-only model in polar aprotic solvent. (For the first reduction potential, SM8 shows similar performance to PCM.) SM8 model, however, predicts no favorable IP interaction, so is unable to remedy the problems with PCM. In other words, the IP-corrected PCM model remains preferred over the SM8 model. S13
14 Table S4. The first reduction potential at different local minima (w/ and w/o H-bond), and numerical value of each interaction. (in V) w/ H-bond w/o H-bond H-bond (Theory) a H-bond (Expt.) b ther c dh dh dh dh a) Theoretical estimation of H-bond is made by the difference of V(w/ H-bond) V(w/o H-bond). b) Ashnagar, A.; Bruce, J.; Dutton, P.; Prince, R. C. ne- and Two-Electron Reduction of Hydroxy-1,4-naphthoquinones and Hydroxy-9,10-anthraquinones. Biochim. Biophys. Acta 1984, 801, c) The other interaction refers to the sum of mesomeric and inductive effect. This is estimated by the difference of V(w/o H-bond) V(AQ). Another local minimum of the dihydroxyl-substituted species exists where the hydrogen atoms in the hydroxyl groups hydrogen are placed far from the carbonyl groups to prevent the hydrogen atom from forming the intramolecular H-bond. The mesomeric and inductive effect of the H groups on the reduction potential can be separated out at these geometries, and the numerical values of H-bond are listed in Table S4. The all of the local minima w/o H-bond are predicted to have lower reduction potential than AQ. The net H-bond effect can be estimated by the differences of reduction potential between the local (w/o H-bond) and global minimum (w/ H-bond). Theoretically determined H-bond interaction overestimates the measured value of V for di-substitution and V for monosubstitution. (H-bond (Expt.) column in Table S4) The mesomeric and inductive effect of two H groups are estimated to lower reduction potential as expected, since the H group is one of EDGs. (See the last column in Table S4) S14
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