SUPPORTING INFORMATION. for. Maja Lambert, Lars Olsen, and Jerzy W. Jaroszewski* Contents
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1 SUPPORTING INFORMATION for Stereoelectronic Effects on 1 H NMR Chemical Shifts in Methoxybenzenes Maja Lambert, Lars Olsen, and Jerzy W. Jaroszewski* Contents 1. General Experimental Procedures: page S2 2. Calculations: page S2 3. Table S1. 1 H NMR Chemical Shifts for Model Compounds 3-16: page S3 4. Table S2. Structures of Different Conformations of Compounds 3-16 Calculated in the Gas Phase: page S3 5. Table S3. Structures of Different Conformations of Compounds 3-16 Calculated in Chloroform: page S5 6. Table S4. Cartesian Atomic Coordinates of Conformers of Compounds 3-16 Calculated in the Gas Phase: page S7 7. Table S5. Cartesian Atomic Coordinates of Conformers of Compounds 3-16 Calculated in Chloroform: page S1 8. Table S6. Nuclear Shieldings (σ, ppm) for Different Conformations of Compounds 3-16 Calculated in the Gas Phase: page S13 9. Table S7. Nuclear Shieldings (σ, ppm) for Different Conformations of Compounds 3-16 Calculated in Chloroform: page S14 1. Table S8. Mean Average Errors for Calculated Chemical Shifts of Various Conformations of 3-16: page S H NMR Spectra of Compounds 9-16 in CDCl 3 : page S17 S1
2 General Experimental Procedures Preparative HPLC separations were performed on a preparative HPLC system consisting of a degasser, pump, autosampler, automatic fraction collector and a PDA detector operating at 254 nm, using a 25 cm x 2 cm i.d., 5 µm particle size C 18 column; linear gradient of CH 3 CN (1 to 6% during 3 min) in H 2 O (.1 % formic acid) at a flow rate of 2 ml/min was used. NMR spectra were recorded at 25 C in chloroform-d (99.8 % deuterium) on a 6 MHz spectrometer equipped with a 5 mm inverse-configuration probe, using TMS as internal reference. Sensitivity-enhanced 1 H- 13 C HSQC, 1 H- 13 C HMBC (optimized for J C,H = 7.7 Hz), and NOESY (mixing time 6 ms) were recorded using standard library pulse sequences. Compounds 3-8, 2, 3, 4-trihydroxybenzaldehyde, and 2, 3, 4-trimethoxybenzaldehyde were obtained from commercial suppliers. Solvents were HPLC grade and water was purified by deionization and.22-µm membrane filtration. Calculations Initial conformations were generated by a Monte Carlo search using the MMFF force field. All DFT calculations were carried out with the Gaussian3 quantum mechanical package 12 using the hybrid density functional method B3LYP. The structures were geometry-optimized without symmetry constraints using the 6-31G** basis set, separately in vacuo and in solvent (chloroform). Single-point calculations and chemical shielding calculations (with the GIAO method) of the G-31D** optimized geometries were performed at the G(2d,2p) level. Calculated nuclear shieldings of degenerate conformations were averaged as appropriate. Solvent calculations were performed using the CPCM approach, which is an implementation of the conductor-like screening solvation model (COSMO) in Gaussian3. S2
3 TABLE S1. 1 H NMR Chemical Shifts for Model Compounds 3-16 in CDCl 3 Relative to Internal TMS cpd. systematic name Chemical shift, δ aromatic H CH 3 OCH 3 3 1,2,3-benzenetriol 6.49 (H-4, H-6), 6.68 (H-5) 4 3-methoxy-1,2-benzenediol 6.48 (H-4), 6.76 (H-5), (H-6) 5 2-methoxy-1,3-benzenediol 6.51 (H-4, H-6), 6.87 (H-5) ,3-dimethoxyphenol 6.48 (H-4), 6.93 (H-5), 6.6 (H-6) 3.9 (2-OCH 3 ), 3.86 (2-OCH 3 ) 7 2,6-dimethoxyphenol 6.59 (H-3, H-5), 6.8 (H-4) ,2,3-trimethoxybenzene 6.59 (H-4, H-6), 6.99 (H-5) 3.87 (1- and 3-OCH 3 ), 3.86 (2-OCH 3 ) 9 4-methylbenzene-1,2,3-triol 6.55 (H-5), 6.39 (H-6) methoxy-4-methylbenzene-1,2-diol 6.6 (H-5), 6.65 (H-6) methoxy-4-methylbenzene-1,3-diol 6.75 (H-5), 6.43 (H-6) methoxy-6-methylbenzene-1,2-diol 6.38 (H-4), 6.61 (H-5) ,3-dimethoxy-4-methylphenol 6.77 (H-5), 6.62 (H-6) (2-OCH 3 ), 3.83 (3-OCH 3 ) 14 2,3-dimethoxy-6-methylphenol 6.38 (H-4), 6.78 (H-5) (2-OCH 3 ), 3.89 (3-OCH 3 ) 15 2,6-dimethoxy-3-methylphenol 6.63 (H-4), 6.57 (H-5) (2-OCH 3 ), 3.87 (6-OCH 3 ) 16 1,2,3-trimethoxy-4-methylbenzene 6.82 (H-5), 6.58 (H-6) (1-OCH 3 ), 3.87 (2- OCH 3 ), 3.83 (3-OCH 3 ) TABLE S2. Structures of Different Conformations of Compounds 3-16 Calculated in the Gas Phase a cpd. Conformations in gas phase with relative energies (kj/mol) conformation 1 conformation 2 conformation 3 conformation 4 conformation S3
4 S4
5 a Structures optimized at the B3LYP/6-31G** level, energies calculated at the B3LYP/ G(2d,2p) level. TABLE S3. Structures of Different Conformations of Compounds 3-16 Calculated in Chloroforma cpd. conformation 1 Conformations in chloroform with relative energies (kj/mol) conformation 2 conformation 3 conformation 4 conformation S5
6 Structures optimized at the B3LYP/6-31G** level, energies calculated at the B3LYP/ G(2d,2p) level with the CPCM solvent model. a S6
7 TABLE S4. Cartesian Atomic Coordinates of Conformers of Compounds 3-16 Calculated in the Gas Phase a cpd. conformation 1 conformation 2 conformation 3 conformation 4 conformation C C C C C C H O O H H O H H H C C C C C C H O O H H O H H C H H H C C C C C C H C O O H H O H H H H H C C C C C C H C O O H H O H H C H H H H H C C C C C C H H O O H H O C C H H H H H H C C C C C C H O O H H O H H H C C C C C C H O O H H O H H C H H H C C C C C C H C O O H H O H H H H H C C C C C C H C O O H H O H H C H H H H H C C C C C C H H O O H H O C C H H H H H H S7
8 8 C C C C C C H C O O H H O H C C H H H H H H H H C C C C C C H C O O H H O H C C H H H H H H H H C C C C C C H C O O H H O H C C H H H H H H H H C C C C C C H C O O H H O H C C H H H H H H H H C C C C C C H O O H O H H H C H H H C C C C C C H O O H O H H H C H H H C C C C C C H O O H O H H H C H H H C C C C C C O O H H O H H C H H H C H H H C C C C C C O O H H O H H C H H H C H H H C C C C C C H C O O H O H H H H H C H H H C C C C C C H C O O H O H H H H H C H H H C C C C C C H C O O H O H H H H H C H H H C C C C C C H O O H O H H C H H H C H C C C C C C H O O H O H H C H H H C H S8
9 H H H H C C C C C C C O O H H O H H C H H H H H C H H H C C C C C C C O O H H O H H C H H H H H C H H H C C C C C C H C O O H O H H C H H H H H C H H H C C C C C C H C O O H O H H C H H H H H C H H H C C C C C C H H O O H O C C H H H H H H C H H H C C C C C C H H O O H O C C H H H H H H C H H H C C C C C C H H O O H O C C H H H H H H C H H H C C C C C C H C O O H O H C C H H H H H H H H C H H H C C C C C C H C O O H O H C C H H H H H H H H C H H H a DFT structures optimized at the B3LYP/6-31G** level. C C C C C C H C O O H O H C C H H H H H H H H C H H H C C C C C C H C O O H O H C C H H H H H H H H C H H H C C C C C C H C O O H O H C C H H H H H H H H C H H H S9
10 TABLE S5. Cartesian Atomic Coordinates of Conformers of Compounds 3-16 Calculated in Chloroform a cpd. conformation 1 conformation 2 conformation 3 conformation 4 conformation C C C C C C H O O H H O H H H C C C C C C H O O H H O H H C H H H C C C C C C H C O O H H O H H H H H C C C C C C H C O O H H O H H C H H H H H C C C C C C H H O O H H O C C H H H H H H C C C C C C H O O H H O H H H C C C C C C H O O H H O H H C H H H C C C C C C H C O O H H O H H H H H C C C C C C H C O O H H O H H C H H H H H C C C C C C H H O O H H O C C H H H H H H S1
11 8 C C C C C C H C O O H H O H C C H H H H H H H H C C C C C C H C O O H H O H C C H H H H H H H H C C C C C C H C O O H H O H C C H H H H H H H H C C C C C C H C O O H H O H C C H H H H H H H H C C C C C C H O O H O H H H C H H H C C C C C C H O O H O H H H C H H H C C C C C C H O O H O H H H C H H H C C C C C C O O H H O H H C H H H C H H H C C C C C C O O H H O H H C H H H C H H H C C C C C C H C O O H O H H H H H C H H H C C C C C C H C O O H O H H H H H C H H H C C C C C C H C O O H O H H H H H C H H H C C C C C C H O O H O H H C H H H C H C C C C C C H O O H O H H C H H H C H S11
12 H H H H C C C C C C C O O H H O H H C H H H H H C H H H C C C C C C C O O H H O H H C H H H H H C H H H C C C C C C H C O O H O H H C H H H H H C H H H C C C C C C H C O O H O H H C H H H H H C H H H C C C C C C H H O O H O C C H H H H H H C H H H C C C C C C H H O O H O C C H H H H H H C H H H C C C C C C H H O O H O C C H H H H H H C H H H C C C C C C H C O O H O H C C H H H H H H H H C H H H C C C C C C H C O O H O H C C H H H H H H H H C H H H C C C C C C H C O O H O H C C H H H H H H H H C H H H C C C C C C H C O O H O H C C H H H H H H H H C H H H a DFT structures optimized at the B3LYP/6-31G** level with the CPCM solvent model. C C C C C C H C O O H O H C C H H H H H H H H C H H H S12
13 TABLE S6. Nuclear Shieldings (σ, ppm) for Different Conformations of Compounds 3-16 Calculated in the Gas Phase a experimental Conformations in gas phase cpd. H-atom chemical shift, δ conformation 1 conformation 2 conformation 3 conformation 4 3 H-4, H H H H H OCH H-4, H H OCH H H H OCH OCH H-3, H H OCH 3 6-OCH H-4, H H OCH OCH 3, 3- OCH H H CH H H OCH CH H H OCH CH H H OCH CH H H OCH H CH H conformation 5 S13
14 H OCH OCH CH H H OCH OCH CH H H OCH OCH H CH a Structures were optimized with B3LYP/6-31G** and NMR shielding constants calculated with B3LYP/ G(2d,2p); energy of conformations increases from 1 to 5. TABLE S7. Nuclear Shieldings (σ, ppm) for Different Conformations of Compounds 3-16 Calculated in Chloroform a experimental Conformations in gas phase cpd. H-atom chemical shift, δ conformation 1 conformation 2 conformation 3 conformation 4 3 H-4, H H H H H OCH H-4, H H OCH H H H OCH OCH H-3, H H OCH 3, 6- OCH H-4, H H OCH OCH 3, 3- OCH H H conformation 5 S14
15 CH H H OCH CH H H OCH CH H H OCH CH H H OCH H CH H H OCH OCH CH H H OCH OCH CH H H OCH OCH H CH a Structures were optimized with B3LYP/6-31G** and NMR shielding constants calculated with B3LYP/ G(2d,2p) using the CPCM solvent model. TABLE S8. Mean Average Errors for Calculated Chemical Shifts of Various Conformations of 3-16 a mean average error, ppm compound conformation gas phase chloroform H atoms in H atoms in benzene ring all H atoms benzene ring all H atoms S15
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