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Structure-antibacterial activity relationship of maleic ether compound by density functional theory


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Structure-antibacterial activity relationship of maleic ether compound by density functional theory
Li MingjianChen YanFeng Changjun
School of Chemistry and Chemical Engineering,Xuzhou Institute of Technology,Xuzhou 221111,China
computational chemistry maleic ether antibacterial activity sclerotinia sclerotiorum density functional theory quantitative structure-activity relationship
S482.2; O6-051
The density functional theory(DFT)method of quantum chemistry is used to study the quarititative structure-activity relationship(QSAR)of the antibacterial activities EM50 of 14 maleic ether compounds to sclerotinia sclerotiorum.The DFT-B3LYP method with the basic set 6-31G(d)is employed to calculate the molecular geometries and electronic structures of 14 maleic ether molecules.The energy of the highest occupied molecular orbital EHOMO,the energy of the lowest unoccupied molecular orbital ELUMO,the energy of the next lowest unoccupied molecular orbital ENHOMO,the energy of the next highest occupied molecular orbital ENLUMO,the net charge of atoms in molecules QZ,the dipole moment μ,the vibrational energy at OK Ev,the total energy E,the heat capacity Cv and the entropy Sm are selected as structural descriptors qL.The main independent factors affecting the antibacterial activities EM50 is determined by leaps-and-bounds regression analysis,and then satisfactory QSAR model is established.The good stability and predictive ability of the model are examined by the leave-one-out(LOO)cross-validation method and variance inflation factors VIF.The fitting correlation coefficient R2 and the cross-validation coefficient R2cv are 0.910 and 0.818,respectively.The result suggests that the energy of highest occupied molecular orbital EHOMO and the net charge QO7 of O7 atom are the predominant factors affecting the antibacterial activity against sclerotinia sclerotiorum.The antibacterial activity of the compounds increase with the increase of the EHOMO; however,the higher the QO7 is,the lower the antibacterial activity is.The models may be used as the theoretical reference for the design of new maleic ether compounds with high antibacterial activities.


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Last Update: 2014-10-31