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Volumn 16, Issue 15, 2006, Pages 4095-4098

Proton dissociation is important to understanding structure-activity relationships of gallic acid antioxidants

Author keywords

Antioxidant; Bond dissociation enthalpy; Density functional theory; Gallic acid derivatives; Ionization potential; Structure activity relationships

Indexed keywords

ANTIOXIDANT; GALLIC ACID; PROTON;

EID: 84962385280     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.04.096     Document Type: Article
Times cited : (69)

References (43)
  • 6
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    • note
    • 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.
  • 7
    • 84962335615 scopus 로고    scopus 로고
    • 6b
  • 29
    • 84962433452 scopus 로고    scopus 로고
    • note
    • In vacuo data were also calculated to compare with the in solvent results (see in Supporting information for detail).
  • 31
    • 84962440260 scopus 로고    scopus 로고
    • note
    • 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).
  • 33
    • 84962350795 scopus 로고    scopus 로고
    • 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.
  • 34
    • 84962433417 scopus 로고    scopus 로고
    • 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).
  • 35
    • 84962350790 scopus 로고    scopus 로고
    • 27b
  • 37
    • 84962440255 scopus 로고    scopus 로고
    • note
    • i (-1417.960021 hartree) is the energy of initial molecule.
  • 38
    • 84962440249 scopus 로고    scopus 로고
    • note
    • The big difference between in solvent and in vacuo IPs highlights the necessity of taking solvent effect into consideration in SAR study of antioxidants.
  • 41
    • 84962457384 scopus 로고    scopus 로고
    • note
    • 4
  • 42
    • 84962433445 scopus 로고    scopus 로고
    • note
    • 6b


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.