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84962447913
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note
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4 it cannot interpret the differences between gallic acids and gallic acid esters, such as 1 and 5, because both of them have similar side chains.
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7
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84962335615
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6b
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11
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1842712340
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Kong L., Sun Z.-L., Wang L.-F., Zhang H.-Y., and Yao S.-D. Helv. Chim. Acta 87 (2004) 511
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29
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84962433452
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note
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In vacuo data were also calculated to compare with the in solvent results (see in Supporting information for detail).
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31
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84962440260
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note
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A high-level approach, labeled as (RO)B3LYP/6-311 + G(2d,2p)//(RO)B3LYP/6-31 + G(d)/(RO) B3LYP/6-31 + G(d) (which means that (RO)B3LYP/6-31 + G(d) was used to optimize molecular structures (in solvent) and obtain vibrational frequencies and then (RO)B3LYP/6-311 + G(2d,2p) was employed to give SPE (also in solvent)), was used to calculate O-H BDEs and IPs of GADs 1 (including anion) and 5. Both methods give very similar O-H BDEs and IPs for the GADs, which partially arises from the fact that AM1 behaves as good as (RO)B3LYP/6-31 + G(d) in optimizing molecular structures (see Supporting information for detail).
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33
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84962350795
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaroni, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. 'Gaussian 98, Revision A.11', Gaussian, Inc., Pittsburgh, PA, 2001.
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34
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84962433417
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As Gaussian 98 failed to optimize the structures of some GADs by (RO)B3LYP/6-31 + G(d) in ethanol, Gaussian 03 program was resorted to do calculations for these GADs (see Supporting information for detail).
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35
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84962350790
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27b
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37
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84962440255
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note
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i (-1417.960021 hartree) is the energy of initial molecule.
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38
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84962440249
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note
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The big difference between in solvent and in vacuo IPs highlights the necessity of taking solvent effect into consideration in SAR study of antioxidants.
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41
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84962457384
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note
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4
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42
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84962433445
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note
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6b
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