化合物定量结构与色谱保留相关关系的研究
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摘要
化合物的定量结构-色谱保留相关(OSRR)是色谱学基础理论研究的重要课题,它将被分析物的色谱保留数据与其分子结构特征相关联。QSRR方法在研究分子结构参数与色谱保留性质的递变规律、实现色谱过程中保留数据的预测、选择分离条件及探索色谱保留机制等方面有重要意义,如今越来越受到色谱工作者的重视。
本论文选取意义明确的结构参数,运用多种数理统计方法,构建了含有氮、氧、硫等杂原子的几类化合物集合的气相色谱保留指数模型,结果令人满意。根据建立的QSRR方程探讨了化合物在不同极性色谱柱上的保留机理。论文主要包括以下几方面的工作:
(一)构建了烷基吡啶类化合物在两种不同极性固定相(SE-30和PEG-351)上的气相色谱保留指数的QSRR模型,运用遗传函数近似法得到的QSRR方程具有高度的相关性(R_1~2=0.990,R_2~2=0.989),优选出的结构参数包括了量子化学参数和物理化学参数,经方程得到的保留指数估计值与实验测定值较为一致:还构建了硝基苯甲酸酯类化合物在两种不同极性固定相(SE-30和OV-351)上的OSRR模型,运用多元线性回归方法也得到了高度相关的QSRR方程(R_1=0.9975,R_2=0.9910),采用留一法(LOO)进行交互检验证明了模型的稳定性。
(二)选用烷基苯酚类化合物和饱和酯类化合物作为研究对象,研究了化合物定量结构与色谱保留的相关关系。用遗传函数近似法建立了烷基苯酚类化合物的气相色谱保留指数的QSRR方程,相关性良好(R~2=0.972),经方程得到的保留指数估计值与实验测定值较为一致;又分别用遗传函数近似法和多元线性回归法,构建了在四种不同极性固定相(SE-30、DC-710、XE-60、Silar 5CP)上的饱和酯类化合物的QSRR模型,得到的QSRR方程均具有高度的相关性。由多元线性回归得到的方程其相关系数分别为:R_1=0.9969,R_2=0.9947,R_3=0.9959,R_4=0.9935;由遗传函数近似法得到的方程其相关系数平方分别为:R_1~2=0.9994,R_2~2=0.9972,R_3~2=0.9985,R_4~2=0.9974。对比可知对于该体系用遗传函数近似法得到的OSRR方程相关关系更好。
(三)研究了不饱和取代的硫醚类化合物在四种不同极性固定相(ApiezonM、OV-17、TritonX-305、PEG-1000)上的定量结构与色谱保留的相关关系。用多元线性回归法建立的QSRR方程具有高度的相关性(R_1=0.9984,R_2=0.9982,R_3=0.9940,R_4=0.9911),用留一法验证了模型的稳定性。
通过对含氮、氧、硫等杂原子的几类化合物的QSRR研究,均得到相关性显著的QSRR模型,证明了该方法的可行性。可以用来有效地预测化合物的色谱保留值,并为选择化合物最佳的色谱分离条件提供依据,从而减少实验的盲目性,同时节省了时间和大量的人力物力。
Quantitative structure-retention relationship(QSRR)of compounds is an impotant topic in chromatographic basis study.It relate chromatographic retention data of analyte with its molecular structure.QSRR has significant meaning in many way.It can give information on the relation between molecular structure parameters and chromatographic retention mechanism.It can also help us to predict chromatographic retention data and to select the condition of separate.Nowadays QSRR is more and more recognized by the chromatographic experts.
This paper begins with selecting structure parameters which have specific chemical meaning as molecular descriptors,and then using statistical method,such as multiple linear regression(MLR)and genetic function approximation(GFA),to develop QSRR models.The compounds studied in this paper contain O-、N-、Sgroups. The results indicate that the QSRR models developed are very satisfactory. The major work is described as follows:
(1)QSRR models for the gas chromatographic retention indices of alkyl pyridines on two different polarity stationary phases(SE-30 and PEG-351)have been developed. By using genetic function approximation method,we obtained empirical equations with high correlation(R~2_1 =0.990,R~2_2=0.989).RIpre came from QSRR equation was close to RIref came from reference.Then nitryl-benzoic esters were studied. QSRR models for the gas chromatographic retention indices of nitryl-benzoic esters on two different polarity stationary phases(SE-30 and OV-351)have been developed by using multiple linear regression method.Empirical equation with high correlation(R_1=0.9975,R_2=0.9910)was obtained.Use leave-one-out method to prove the stability of models.
(2)Choosing alkylphenols and saturated ester as object,QSRR of compounds contained O- were studied.By using genetic function approximation method,we obtained QSRR functions of alkylphenols with high correlation(R~2=0.972).Then the retention indices of saturated ester on four different polarity stationary phases(SE-30. DC-710,XE-60,Silar 5CP)was studied.QSRR equations were respectively built with multiple linear regression method and genetic function approximation method.QSRR equations were both good.But by contrast the two method,we found that genetic function approximation method fit to this series of compounds and the equations built by genetic function approximation method were better.The statistical result came from multiple linear regression method was:R_1=0.9969,R_2=0.9947,R_3=0.9959, R_4=0.9935.The result came from genetic function approximation method was: R~2_1=0.9994,R~2_2=0.9972,R~2_3=0.9985,R~2_4=0.9974.They were all considered as high correlation.
(3)QSRR models for the gas chromatographic retention indices of sulfur ether on four different polarity stationary phases(Apiezon M,OV-17,Triton X-305,PEG-1000) were developed.The equations were built with multiple linear regression method. Empirical equation with high correlation(R_1=0.9984,R_2=0.9982,R_3=0.9940, R_4=0.9911)was obtained.Then use leave-one-out method to prove the stability of models.
By studying the compounds contained O-,N-,S- groups,QSRR models with high correlation were obtained.So the feasibility of QSRR method can be proved. QSRR models can be used to predict the chromatographic retention datas and to select the best separation conditions.It can help us save time of experiment and reduce the blindness in the experiment.
本论文选取意义明确的结构参数,运用多种数理统计方法,构建了含有氮、氧、硫等杂原子的几类化合物集合的气相色谱保留指数模型,结果令人满意。根据建立的QSRR方程探讨了化合物在不同极性色谱柱上的保留机理。论文主要包括以下几方面的工作:
(一)构建了烷基吡啶类化合物在两种不同极性固定相(SE-30和PEG-351)上的气相色谱保留指数的QSRR模型,运用遗传函数近似法得到的QSRR方程具有高度的相关性(R_1~2=0.990,R_2~2=0.989),优选出的结构参数包括了量子化学参数和物理化学参数,经方程得到的保留指数估计值与实验测定值较为一致:还构建了硝基苯甲酸酯类化合物在两种不同极性固定相(SE-30和OV-351)上的OSRR模型,运用多元线性回归方法也得到了高度相关的QSRR方程(R_1=0.9975,R_2=0.9910),采用留一法(LOO)进行交互检验证明了模型的稳定性。
(二)选用烷基苯酚类化合物和饱和酯类化合物作为研究对象,研究了化合物定量结构与色谱保留的相关关系。用遗传函数近似法建立了烷基苯酚类化合物的气相色谱保留指数的QSRR方程,相关性良好(R~2=0.972),经方程得到的保留指数估计值与实验测定值较为一致;又分别用遗传函数近似法和多元线性回归法,构建了在四种不同极性固定相(SE-30、DC-710、XE-60、Silar 5CP)上的饱和酯类化合物的QSRR模型,得到的QSRR方程均具有高度的相关性。由多元线性回归得到的方程其相关系数分别为:R_1=0.9969,R_2=0.9947,R_3=0.9959,R_4=0.9935;由遗传函数近似法得到的方程其相关系数平方分别为:R_1~2=0.9994,R_2~2=0.9972,R_3~2=0.9985,R_4~2=0.9974。对比可知对于该体系用遗传函数近似法得到的OSRR方程相关关系更好。
(三)研究了不饱和取代的硫醚类化合物在四种不同极性固定相(ApiezonM、OV-17、TritonX-305、PEG-1000)上的定量结构与色谱保留的相关关系。用多元线性回归法建立的QSRR方程具有高度的相关性(R_1=0.9984,R_2=0.9982,R_3=0.9940,R_4=0.9911),用留一法验证了模型的稳定性。
通过对含氮、氧、硫等杂原子的几类化合物的QSRR研究,均得到相关性显著的QSRR模型,证明了该方法的可行性。可以用来有效地预测化合物的色谱保留值,并为选择化合物最佳的色谱分离条件提供依据,从而减少实验的盲目性,同时节省了时间和大量的人力物力。
Quantitative structure-retention relationship(QSRR)of compounds is an impotant topic in chromatographic basis study.It relate chromatographic retention data of analyte with its molecular structure.QSRR has significant meaning in many way.It can give information on the relation between molecular structure parameters and chromatographic retention mechanism.It can also help us to predict chromatographic retention data and to select the condition of separate.Nowadays QSRR is more and more recognized by the chromatographic experts.
This paper begins with selecting structure parameters which have specific chemical meaning as molecular descriptors,and then using statistical method,such as multiple linear regression(MLR)and genetic function approximation(GFA),to develop QSRR models.The compounds studied in this paper contain O-、N-、Sgroups. The results indicate that the QSRR models developed are very satisfactory. The major work is described as follows:
(1)QSRR models for the gas chromatographic retention indices of alkyl pyridines on two different polarity stationary phases(SE-30 and PEG-351)have been developed. By using genetic function approximation method,we obtained empirical equations with high correlation(R~2_1 =0.990,R~2_2=0.989).RIpre came from QSRR equation was close to RIref came from reference.Then nitryl-benzoic esters were studied. QSRR models for the gas chromatographic retention indices of nitryl-benzoic esters on two different polarity stationary phases(SE-30 and OV-351)have been developed by using multiple linear regression method.Empirical equation with high correlation(R_1=0.9975,R_2=0.9910)was obtained.Use leave-one-out method to prove the stability of models.
(2)Choosing alkylphenols and saturated ester as object,QSRR of compounds contained O- were studied.By using genetic function approximation method,we obtained QSRR functions of alkylphenols with high correlation(R~2=0.972).Then the retention indices of saturated ester on four different polarity stationary phases(SE-30. DC-710,XE-60,Silar 5CP)was studied.QSRR equations were respectively built with multiple linear regression method and genetic function approximation method.QSRR equations were both good.But by contrast the two method,we found that genetic function approximation method fit to this series of compounds and the equations built by genetic function approximation method were better.The statistical result came from multiple linear regression method was:R_1=0.9969,R_2=0.9947,R_3=0.9959, R_4=0.9935.The result came from genetic function approximation method was: R~2_1=0.9994,R~2_2=0.9972,R~2_3=0.9985,R~2_4=0.9974.They were all considered as high correlation.
(3)QSRR models for the gas chromatographic retention indices of sulfur ether on four different polarity stationary phases(Apiezon M,OV-17,Triton X-305,PEG-1000) were developed.The equations were built with multiple linear regression method. Empirical equation with high correlation(R_1=0.9984,R_2=0.9982,R_3=0.9940, R_4=0.9911)was obtained.Then use leave-one-out method to prove the stability of models.
By studying the compounds contained O-,N-,S- groups,QSRR models with high correlation were obtained.So the feasibility of QSRR method can be proved. QSRR models can be used to predict the chromatographic retention datas and to select the best separation conditions.It can help us save time of experiment and reduce the blindness in the experiment.
引文
[1]A.J.P.Martin,Some theoretical aspects of partition chromatography,Bilchem Soc.Symp.,1950.3:4-22
[2]J.Green,S.Marcinkiewicz,D.Mchal,Paper chromatography and chemical structure,J.Chromatogr.,1963,10:158-166
[3]J.Iwasa,T.Fujita,C.Hansch,Substituent constants for aliphatic functions obtained from partition coefficients,J.Med.Chem.,1965,8:150-158
[4]E.Tomlinson,Chromatographic hydrophobic parameters in correlation analysis of structure-activity relationships,J.Chromatogr.,1975,113:1-12
[5]R.Kaliszan,Chromatography in studies of quantitative structure-activity relation ships,J.Chromatogr.,1981,220:71-84
[6]R.Kaliszan,High performance liquid chromatography as a source of structural information for medicinal chemistry,J.Chromatogr.Sci.,1984,22:362-370
[7]R.Kaliszan,Quantitative relationships between molecular structure and chromato graphic retention,Implications in physical,analytical and chemistry,Crit.Rev.Anal.Chem.,1986,16:323-341
[8]R.Kaliszan,H.Fork,The relationship between the R_M values and the connectivity indices for pyrazine carbothioamide derivatives,Chromatographia,1977,10:346-355
[9]R.Kaliszan,Correlation between the retention indices and the connectivity indices of alcohols and methyl esters with complex cyclic structure.Chromatographia,1977,10:529-540
[10]I.Michotte,D.L.Massart,Molecular connectivity and retention indexes,J.Pharm.Sci.,1977,66:1630-1654
[11]戴朝政,卢佩章,李浩春,关于分子结构与气相色谱保留规律的研究,色谱,1988,6(2):81-86
[12]D.Papazova,N.Dimov,Study of the relationship between the molecular structure and gas chromatographic retention of alkenes on squalane,J.Chromatogr.,1977,137:2 59-264
[13]N.Dimov,An exacte quation of solute for the calculation of the retention indices of isoalkanes on squalane,J.Chromatogr.,1976,119:109-118
[14]N.Dimov,A.Osman,Selection of molecular descriptors used in quantitative structure-gas chromatographic retention relationships,Anal.Chim.Acta,1996.323:15-25
[15]J.Novak,J.Vejrosta,M.Roth,J.Janak,Correlation of gas chromatographic specific retention volumes of homologous compounds with temperature and methylene number,J.Chromatogr.,1980,199:209-216
[16]M.Gassiot,E.Fernandez,G.Firpo,R.Carbo,M.Martin,Empirical quantum chemical approach to structure-gas chromatographic retention index relationships,J.Chromatogr.,1975,108:337-344
[17]L.Buydens,D.L.Massart,P.Geerlings,Prediction of gas chromatographic retention indexes with topological,Physicochemical and Quantum Chemical Parameters,Anal.Chem.,1983,55(4):738-744
[18]F.Saura-Calixto,A.Garcia-Raso,M.A.Raso,Study of the applications of magnitudes of energy and charge of molecular orbitals to GC retention-easters.J.Chromatogr.,1984,22(1):22-26
[19]王亚伟,高玉红,姚小军等,单硫醚在不同极性固定相上的气相色谱保留指数与结构的相关性研究,色谱,2002,20(5):415-418
[20]施介华,江峰,严巍等,酯在聚硅氧烷类固定相上的色谱保留机理研究,浙江工业大学学报,2004,32(4):418-422
[21]Yuhong Gao,Yawei Wang,Xiaojun Yao,Mancang Liu,The prediction for gas chromatographic retention index of disulfides on stationary phases of different polarity,Talanta,2003,59:229-237
[22]D.Bonchev,Ov.Mekenjan,G.Protic,N.Trinajastic,Application of topological indices to gas chromatographic data:calculation of the retention indices of isomeric alkylbenzenes,J.Chromatogr.,1979,176:149-156
[23]M.Randic,On characterization of molecular branching,J.Am.Chem.Soc.,1975.97:6609-6623
[24]M.Randic,The structural origin of chromatographic retention data,J.Chromato gr.,1978,161:1-14
[25]L.B.Kier,L.H.Hall,M.J.Murray.M.Randic,Molecular connectivity Ⅰ:relationship to nonspecific local anesthesia,J.Pharm.Sci.,1975,64(12):1971-1974
[26]Lowell H.Hall,Lemont B.Kier,Molecular connectivity and substructure analysis,J.Pharm.Sci.,1978,67(12):1743-1747
[27]L.B.Kier,L.H.Hall,Molecular connectivity in structure activity analysis,Research Studies Press Ltd.,Wiley,1986,18-20
[28]Chunhui Lu,Weimin Guo,Chunsheng Yin,A Lu index for QSAR/QSPR studies,Chemical Physics Letters,2006,417:11-15
[29]Chunhui Lu,Weimin Guo,Chunsheng Yin,Quantitative structure-retention relationship study of the gas chromatographic retention indices of saturated esters on different stationary phases using novel topological indices,Anal.Chim.Acta,2006.561:96-102
[30]Fengping Liu,Yizeng Liang,Chenzhong Cao,Neng Zhou,QSPR study of GC retention indices for saturated esters on seven stationary phases based on novel topological indices,Talanta,2007,72:1307-1315
[31]Vilma E.F.Heinzen,Miriam F.Soares,Rosendo A.Yunes,Semi-empirical topological method for the prediction of the chromatographic retention of cis- and trans-alkene isomers and alkanes,J.Chromatogr.A.,1999,849:495-506
[32]姚瑜元,许禄,袁秀顺,有机化合物的结构-活性相关性研究-三个新的拓扑指数及其应用,化学学报,1991,51(11):1041-1047
[33]申琦,许禄,李华,新拓扑指数Am在构效关系研究中的应用,分析化学,1996,24(10):1152-1155
[34]冯长君,堵锡华,胺类化合物Kovats指数的拓扑研究,色谱,2001,19(2):124-127
[35]Palagiri Tulasamma,Kalluru Subramanyam Reddy,Quantitative structure and retention relationships for gas chromatographic data:Application to alkyl pyridines on apolar and polar phases,J.Molecular Graphics and Modelling,2006,25:507-513
[36]郭伟强,分子识别原理在色谱保留值定量化描述中的应用研究,浙江大学博士学位论文,2002
[37]许禄,化学计量学,第一版,北京:科学出版社,1985:339-349
[38]L.Ekievt,Z.G.Zachwieja,J.Bojarski,Quasi-column chromatography of barbituric acid derivatives Ⅱ.Separation on Non-polar adsorbents using binary water-organic solvent mixtures as the mobile phase,Chromatographia.1980,13(8):472-478
[39]J.Bermejo,M.D.Guillen,Prediction of Kovats retention index of saturated alcohols on stationary phases of different polarity,Anal.Chem.,1987,59(1):94-97
[40]A.R.Katritzky,E.S.Ignatchenko,R.A.Barcock,Prediction of gas chromato graphic retention times and response factors using a general quatitative structure-property relationships treatment,Anal.Chem.,1994,66(11):1799-1807
[41]J.Olivero,K.Kannan,Quantitative structure-retention relationships of polychlorinated naphthalenes in gas chromatography,J.Chromatogr.A.,1999,849:621-627
[42]Yawei Wang,Xiaojun Yao,Xiaoyun Zhang,Mancang Liu,The prediction for gas chromatographic retention indices of saturated esters on stationary phases of different polarity,Talanta,2002,57:641-652
[43]Yawei Wang,An Li,Guibin Jiang,Development of quantitative structure gas chr- omatographic relative retention time models on seven stationary phases for 209poly- brominated diphenyl ether congeners,J.Chromatogr.A.,2006,1103:314-328
[44]韩海洪,有机醇的结构与色谱保留指数的相关性拓扑指数法研究,计算机与应用化学,2003,20(5):687-689
[45]郄毅巍,李江波,曹维良等,环醇和酯的定量结构.保留关系的研究,北京化工大学学报,2003,30(3):85-88
[46]严海英,韩海洪,低沸点烷烃Kovats指数的拓扑结构研究,青海师范大学学报(自然科学版),2004,4:51-53
[47]刘利,曹晨忠,谢斌,邹立科,硫醚、硫醇色谱保留指数的QSRR研究,湖南科技大学学报(自然科学版),2005,20(4):74-79
[48]刘红艳,王遵尧,刘树深,翟志才,多氯萘的气相色谱保留指数与其结构参数的定量关系,色谱,2005,23(4):336-340
[49]Rong-Jing Hu,Huan-Xiang Liu,Rui-Sheng Zhang,QSPR prediction of GC retention indices for nitrogen-containing polycyclic aromatic compounds from heuristically computed molecular descriptors,Talanta,2005,68:31-39
[50]寇建仁,张生万,胡永钢等,不同极性固定相上醇色谱保留指数的预测,化学通报,2006,3:196-200
[51]Corwin Hansch,Robert Muir,Toshio Fujita,The correlation of biological activity of plant growth regulators and chloromycetin derivatives with hammett constants and partition coefficients,J.Am.Chem.Soc.,1963,85(18):2817-2824
[52]A.G..Fragkaki,M.A.Koupparis,C.G.Georgakopoulos,Quantitative structure-retention relationship study of α-,β-,and β_2-agonists using multiple linear regression and partial least-squares procedures,Anal.Chim.Acta,2004,512:165-171
[53]Orsolya Farkas,Karoly Héberger,Igor G.Zenkevich,Quantitative structure-retention relationships XIV prediction of gas chromatographic retention indices for saturated O-,N-,and S-heterocyclic compounds,Chemometrics and intelligent laborAtory systems,2004,72:173-184
[54]Tim Hancock,Raf Put,Danny Coomans,A performance comparison of modern statistical techniques for molecular descriptor selection and retention prediction in chromatographic QSRR studies,Chemometrics and intelligent laboratory systems,2005,76:185-196
[55]代振宇,陈维红,周涵,杨海鹰,色谱保留时间-结构参数定量关系研究,色谱,2000,18(2):125-127
[56]J.Thomas Leonard,Kunal Roy,Exploring molecular shape analysis of styrylquinoline derivatives as HIV-1 integrase inhibitors,J.Medi.Chem.,2008,43:81-92
[57]Pramod C.Nair,M.Elizabeth Sobhia,Quantitative structure activity relationship studies on thiourea analogues as influenza virus neuraminidase inhibitors,J.Medi.Chem.,2008,43:293-299
[58]刘树深,有机物分子电性距离矢量表征及其应用,北京:高等教育出版社,2005,70
[59]R.Kaliszan,Quantitative structure retention relationships,Anal.Chem.,1992.64(11):619-631
[60]Simion Gocan,Florin Irimie,Prediction of the lipophilicity of some plant growth-stimulating amido esters of ethanolamine using reversed-phase thin-layer chromatography,J.Chromatogr.A.,1994,675(1-2):282-285
[61]M.Kucha r,V.Rejholec,E.Kraus,V.Miller,Influence of intramolecular interactions on chromatographic behaviour of arylaliphatic acid:I.Comparison of reversed-phase thin-layer and high-performance liquid chromatography,J.Chromatogr.A.,1983,280:279-288
[62]B.Kocjan,J.Sliwiok,Chromatographic and spectroscopic comparison of the hydrophobilicity of vitamins D2 and D3,J.Planar of Chromatogr.,Modern TLC.1994,7:327-328
[63]Gabriela Cimpan,Cristina Bota,Mioara Coman,Nelu Grinberg,Simion Gocan,A lipophilicity study for some 2-hydrazinothiazolic derivatives with antifungal activity by reversed phase thin layer chromatography,J.Liq.Chromatogr.&Rel.Technol.,1999,22(1):29-40
[64]A.Pahliara,E.Khamis,A.Trinh,P.A.Carrupt,R.S.Testa,Structural properties governing retention mechanisms on RP-HPLC stationary phases used for lipophilicity measurements,J.Liq.Chromatogr.&Rel.Technol.,1995,18(9):1721-1745
[65]J.Thomas,O.Adetchessi,F.Pehourcq,P.Dallet,C.Jarry,Determination of partition coefficients of 2-amino-2-oxazolines by RP-HPLC:application to hydrophobicity studies,J.Liq.Chromatogr.&Rel.Technol.,1997,20(5):671-679
[66]Marcela Longhi,Marcela Linares,Maria M.de Bertorello,High performance liquid chromatography of isoxazolyl-naphthoquinones:a comparison between experimental and theoretical lipophilicity,J.Liq.Chromatogr.&Rel.Technol.,1996,19(12):1947-1956
[67]邹汉法,张玉奎,洪名放,舒玉瑛,卢佩章,反相液相色谱中溶质保留值与溶剂化结构参数间的定量关系,化学学报,1995,53:269-274
[68]Hanfa Zou,YuKui Zhang,Peizhang Lu,Effect of molecular structure on the solute-micelle and solute-stationary phase binding constants in micellar liquid chromatography,Anal.Chem.Acta,1995,310:461-471
[69]A.Pyka,Topological indexes and R[M]values of the pKa values of isomeric methylphenols,chlrophenols and nitrophenols,Part X,J.Planar Chromatogr.. Modern TLC,1996,9:52-55
[70]A.Pyka,Topological indexes and R[M]values of the pKa values of isomeric methylanilines and chloroanilines,J.Planar of Chromatogr.,Modern TLC.,1998.11:61-63
[71]C.B.C.Boyce,B.V.Milborrow,A simple assessment of partition data for correlating structure and biological activity using thin-layer chromatography,Nature,1965,208:537-539
[72]Corwin Hansch,Toshio Fujita,ρ-σ-π Analysis-A method for the correlation of biological activity and chemical structure,J.Am.Chem.Soc.,1964,86:1616-1626
[73]A.M.Barbaro,M.C.Guerra,G..Cantelli Forti,G..Alcardi,G.L.Biagi,RM values of xanthone derivatives in structure-activity studies,J.Chromatogr.A.,1982,242(1):1-7
[74]A.Pyka,The topological indices and R[M]values of benzoic acid derivatives:a structure activity investigation IV,J.Plan.Chromatogr.,Modem TLC.,1994,7:108-116
[75]R.D.Puri,S.V.Mirgal,C.S.Ramma,V.M.Kulkarni,Indian J.Chem.Sect B:Org.Chem.,1996,35(B):1271
[76]Emelita D.Breyer,Joost K.Strasters,Morteza G..Khaledi,Quantitative retention biological activity relationship study by micellar liquid chromatography,Anal.Chem.,1991,63,828-833
[77]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,548
[78]M.J.S.Dewar,E.G.Zoebisch,E.F.Healy,Development and use of quantum mechanical molecular models..AMI:a new general purpose quantum mechanical molecular model,J.Am.Chem.Soc.,1985,107:3902-3909
[79]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,542-543
[80]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,506
[81]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,514
[82]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,57
[2]J.Green,S.Marcinkiewicz,D.Mchal,Paper chromatography and chemical structure,J.Chromatogr.,1963,10:158-166
[3]J.Iwasa,T.Fujita,C.Hansch,Substituent constants for aliphatic functions obtained from partition coefficients,J.Med.Chem.,1965,8:150-158
[4]E.Tomlinson,Chromatographic hydrophobic parameters in correlation analysis of structure-activity relationships,J.Chromatogr.,1975,113:1-12
[5]R.Kaliszan,Chromatography in studies of quantitative structure-activity relation ships,J.Chromatogr.,1981,220:71-84
[6]R.Kaliszan,High performance liquid chromatography as a source of structural information for medicinal chemistry,J.Chromatogr.Sci.,1984,22:362-370
[7]R.Kaliszan,Quantitative relationships between molecular structure and chromato graphic retention,Implications in physical,analytical and chemistry,Crit.Rev.Anal.Chem.,1986,16:323-341
[8]R.Kaliszan,H.Fork,The relationship between the R_M values and the connectivity indices for pyrazine carbothioamide derivatives,Chromatographia,1977,10:346-355
[9]R.Kaliszan,Correlation between the retention indices and the connectivity indices of alcohols and methyl esters with complex cyclic structure.Chromatographia,1977,10:529-540
[10]I.Michotte,D.L.Massart,Molecular connectivity and retention indexes,J.Pharm.Sci.,1977,66:1630-1654
[11]戴朝政,卢佩章,李浩春,关于分子结构与气相色谱保留规律的研究,色谱,1988,6(2):81-86
[12]D.Papazova,N.Dimov,Study of the relationship between the molecular structure and gas chromatographic retention of alkenes on squalane,J.Chromatogr.,1977,137:2 59-264
[13]N.Dimov,An exacte quation of solute for the calculation of the retention indices of isoalkanes on squalane,J.Chromatogr.,1976,119:109-118
[14]N.Dimov,A.Osman,Selection of molecular descriptors used in quantitative structure-gas chromatographic retention relationships,Anal.Chim.Acta,1996.323:15-25
[15]J.Novak,J.Vejrosta,M.Roth,J.Janak,Correlation of gas chromatographic specific retention volumes of homologous compounds with temperature and methylene number,J.Chromatogr.,1980,199:209-216
[16]M.Gassiot,E.Fernandez,G.Firpo,R.Carbo,M.Martin,Empirical quantum chemical approach to structure-gas chromatographic retention index relationships,J.Chromatogr.,1975,108:337-344
[17]L.Buydens,D.L.Massart,P.Geerlings,Prediction of gas chromatographic retention indexes with topological,Physicochemical and Quantum Chemical Parameters,Anal.Chem.,1983,55(4):738-744
[18]F.Saura-Calixto,A.Garcia-Raso,M.A.Raso,Study of the applications of magnitudes of energy and charge of molecular orbitals to GC retention-easters.J.Chromatogr.,1984,22(1):22-26
[19]王亚伟,高玉红,姚小军等,单硫醚在不同极性固定相上的气相色谱保留指数与结构的相关性研究,色谱,2002,20(5):415-418
[20]施介华,江峰,严巍等,酯在聚硅氧烷类固定相上的色谱保留机理研究,浙江工业大学学报,2004,32(4):418-422
[21]Yuhong Gao,Yawei Wang,Xiaojun Yao,Mancang Liu,The prediction for gas chromatographic retention index of disulfides on stationary phases of different polarity,Talanta,2003,59:229-237
[22]D.Bonchev,Ov.Mekenjan,G.Protic,N.Trinajastic,Application of topological indices to gas chromatographic data:calculation of the retention indices of isomeric alkylbenzenes,J.Chromatogr.,1979,176:149-156
[23]M.Randic,On characterization of molecular branching,J.Am.Chem.Soc.,1975.97:6609-6623
[24]M.Randic,The structural origin of chromatographic retention data,J.Chromato gr.,1978,161:1-14
[25]L.B.Kier,L.H.Hall,M.J.Murray.M.Randic,Molecular connectivity Ⅰ:relationship to nonspecific local anesthesia,J.Pharm.Sci.,1975,64(12):1971-1974
[26]Lowell H.Hall,Lemont B.Kier,Molecular connectivity and substructure analysis,J.Pharm.Sci.,1978,67(12):1743-1747
[27]L.B.Kier,L.H.Hall,Molecular connectivity in structure activity analysis,Research Studies Press Ltd.,Wiley,1986,18-20
[28]Chunhui Lu,Weimin Guo,Chunsheng Yin,A Lu index for QSAR/QSPR studies,Chemical Physics Letters,2006,417:11-15
[29]Chunhui Lu,Weimin Guo,Chunsheng Yin,Quantitative structure-retention relationship study of the gas chromatographic retention indices of saturated esters on different stationary phases using novel topological indices,Anal.Chim.Acta,2006.561:96-102
[30]Fengping Liu,Yizeng Liang,Chenzhong Cao,Neng Zhou,QSPR study of GC retention indices for saturated esters on seven stationary phases based on novel topological indices,Talanta,2007,72:1307-1315
[31]Vilma E.F.Heinzen,Miriam F.Soares,Rosendo A.Yunes,Semi-empirical topological method for the prediction of the chromatographic retention of cis- and trans-alkene isomers and alkanes,J.Chromatogr.A.,1999,849:495-506
[32]姚瑜元,许禄,袁秀顺,有机化合物的结构-活性相关性研究-三个新的拓扑指数及其应用,化学学报,1991,51(11):1041-1047
[33]申琦,许禄,李华,新拓扑指数Am在构效关系研究中的应用,分析化学,1996,24(10):1152-1155
[34]冯长君,堵锡华,胺类化合物Kovats指数的拓扑研究,色谱,2001,19(2):124-127
[35]Palagiri Tulasamma,Kalluru Subramanyam Reddy,Quantitative structure and retention relationships for gas chromatographic data:Application to alkyl pyridines on apolar and polar phases,J.Molecular Graphics and Modelling,2006,25:507-513
[36]郭伟强,分子识别原理在色谱保留值定量化描述中的应用研究,浙江大学博士学位论文,2002
[37]许禄,化学计量学,第一版,北京:科学出版社,1985:339-349
[38]L.Ekievt,Z.G.Zachwieja,J.Bojarski,Quasi-column chromatography of barbituric acid derivatives Ⅱ.Separation on Non-polar adsorbents using binary water-organic solvent mixtures as the mobile phase,Chromatographia.1980,13(8):472-478
[39]J.Bermejo,M.D.Guillen,Prediction of Kovats retention index of saturated alcohols on stationary phases of different polarity,Anal.Chem.,1987,59(1):94-97
[40]A.R.Katritzky,E.S.Ignatchenko,R.A.Barcock,Prediction of gas chromato graphic retention times and response factors using a general quatitative structure-property relationships treatment,Anal.Chem.,1994,66(11):1799-1807
[41]J.Olivero,K.Kannan,Quantitative structure-retention relationships of polychlorinated naphthalenes in gas chromatography,J.Chromatogr.A.,1999,849:621-627
[42]Yawei Wang,Xiaojun Yao,Xiaoyun Zhang,Mancang Liu,The prediction for gas chromatographic retention indices of saturated esters on stationary phases of different polarity,Talanta,2002,57:641-652
[43]Yawei Wang,An Li,Guibin Jiang,Development of quantitative structure gas chr- omatographic relative retention time models on seven stationary phases for 209poly- brominated diphenyl ether congeners,J.Chromatogr.A.,2006,1103:314-328
[44]韩海洪,有机醇的结构与色谱保留指数的相关性拓扑指数法研究,计算机与应用化学,2003,20(5):687-689
[45]郄毅巍,李江波,曹维良等,环醇和酯的定量结构.保留关系的研究,北京化工大学学报,2003,30(3):85-88
[46]严海英,韩海洪,低沸点烷烃Kovats指数的拓扑结构研究,青海师范大学学报(自然科学版),2004,4:51-53
[47]刘利,曹晨忠,谢斌,邹立科,硫醚、硫醇色谱保留指数的QSRR研究,湖南科技大学学报(自然科学版),2005,20(4):74-79
[48]刘红艳,王遵尧,刘树深,翟志才,多氯萘的气相色谱保留指数与其结构参数的定量关系,色谱,2005,23(4):336-340
[49]Rong-Jing Hu,Huan-Xiang Liu,Rui-Sheng Zhang,QSPR prediction of GC retention indices for nitrogen-containing polycyclic aromatic compounds from heuristically computed molecular descriptors,Talanta,2005,68:31-39
[50]寇建仁,张生万,胡永钢等,不同极性固定相上醇色谱保留指数的预测,化学通报,2006,3:196-200
[51]Corwin Hansch,Robert Muir,Toshio Fujita,The correlation of biological activity of plant growth regulators and chloromycetin derivatives with hammett constants and partition coefficients,J.Am.Chem.Soc.,1963,85(18):2817-2824
[52]A.G..Fragkaki,M.A.Koupparis,C.G.Georgakopoulos,Quantitative structure-retention relationship study of α-,β-,and β_2-agonists using multiple linear regression and partial least-squares procedures,Anal.Chim.Acta,2004,512:165-171
[53]Orsolya Farkas,Karoly Héberger,Igor G.Zenkevich,Quantitative structure-retention relationships XIV prediction of gas chromatographic retention indices for saturated O-,N-,and S-heterocyclic compounds,Chemometrics and intelligent laborAtory systems,2004,72:173-184
[54]Tim Hancock,Raf Put,Danny Coomans,A performance comparison of modern statistical techniques for molecular descriptor selection and retention prediction in chromatographic QSRR studies,Chemometrics and intelligent laboratory systems,2005,76:185-196
[55]代振宇,陈维红,周涵,杨海鹰,色谱保留时间-结构参数定量关系研究,色谱,2000,18(2):125-127
[56]J.Thomas Leonard,Kunal Roy,Exploring molecular shape analysis of styrylquinoline derivatives as HIV-1 integrase inhibitors,J.Medi.Chem.,2008,43:81-92
[57]Pramod C.Nair,M.Elizabeth Sobhia,Quantitative structure activity relationship studies on thiourea analogues as influenza virus neuraminidase inhibitors,J.Medi.Chem.,2008,43:293-299
[58]刘树深,有机物分子电性距离矢量表征及其应用,北京:高等教育出版社,2005,70
[59]R.Kaliszan,Quantitative structure retention relationships,Anal.Chem.,1992.64(11):619-631
[60]Simion Gocan,Florin Irimie,Prediction of the lipophilicity of some plant growth-stimulating amido esters of ethanolamine using reversed-phase thin-layer chromatography,J.Chromatogr.A.,1994,675(1-2):282-285
[61]M.Kucha r,V.Rejholec,E.Kraus,V.Miller,Influence of intramolecular interactions on chromatographic behaviour of arylaliphatic acid:I.Comparison of reversed-phase thin-layer and high-performance liquid chromatography,J.Chromatogr.A.,1983,280:279-288
[62]B.Kocjan,J.Sliwiok,Chromatographic and spectroscopic comparison of the hydrophobilicity of vitamins D2 and D3,J.Planar of Chromatogr.,Modern TLC.1994,7:327-328
[63]Gabriela Cimpan,Cristina Bota,Mioara Coman,Nelu Grinberg,Simion Gocan,A lipophilicity study for some 2-hydrazinothiazolic derivatives with antifungal activity by reversed phase thin layer chromatography,J.Liq.Chromatogr.&Rel.Technol.,1999,22(1):29-40
[64]A.Pahliara,E.Khamis,A.Trinh,P.A.Carrupt,R.S.Testa,Structural properties governing retention mechanisms on RP-HPLC stationary phases used for lipophilicity measurements,J.Liq.Chromatogr.&Rel.Technol.,1995,18(9):1721-1745
[65]J.Thomas,O.Adetchessi,F.Pehourcq,P.Dallet,C.Jarry,Determination of partition coefficients of 2-amino-2-oxazolines by RP-HPLC:application to hydrophobicity studies,J.Liq.Chromatogr.&Rel.Technol.,1997,20(5):671-679
[66]Marcela Longhi,Marcela Linares,Maria M.de Bertorello,High performance liquid chromatography of isoxazolyl-naphthoquinones:a comparison between experimental and theoretical lipophilicity,J.Liq.Chromatogr.&Rel.Technol.,1996,19(12):1947-1956
[67]邹汉法,张玉奎,洪名放,舒玉瑛,卢佩章,反相液相色谱中溶质保留值与溶剂化结构参数间的定量关系,化学学报,1995,53:269-274
[68]Hanfa Zou,YuKui Zhang,Peizhang Lu,Effect of molecular structure on the solute-micelle and solute-stationary phase binding constants in micellar liquid chromatography,Anal.Chem.Acta,1995,310:461-471
[69]A.Pyka,Topological indexes and R[M]values of the pKa values of isomeric methylphenols,chlrophenols and nitrophenols,Part X,J.Planar Chromatogr.. Modern TLC,1996,9:52-55
[70]A.Pyka,Topological indexes and R[M]values of the pKa values of isomeric methylanilines and chloroanilines,J.Planar of Chromatogr.,Modern TLC.,1998.11:61-63
[71]C.B.C.Boyce,B.V.Milborrow,A simple assessment of partition data for correlating structure and biological activity using thin-layer chromatography,Nature,1965,208:537-539
[72]Corwin Hansch,Toshio Fujita,ρ-σ-π Analysis-A method for the correlation of biological activity and chemical structure,J.Am.Chem.Soc.,1964,86:1616-1626
[73]A.M.Barbaro,M.C.Guerra,G..Cantelli Forti,G..Alcardi,G.L.Biagi,RM values of xanthone derivatives in structure-activity studies,J.Chromatogr.A.,1982,242(1):1-7
[74]A.Pyka,The topological indices and R[M]values of benzoic acid derivatives:a structure activity investigation IV,J.Plan.Chromatogr.,Modem TLC.,1994,7:108-116
[75]R.D.Puri,S.V.Mirgal,C.S.Ramma,V.M.Kulkarni,Indian J.Chem.Sect B:Org.Chem.,1996,35(B):1271
[76]Emelita D.Breyer,Joost K.Strasters,Morteza G..Khaledi,Quantitative retention biological activity relationship study by micellar liquid chromatography,Anal.Chem.,1991,63,828-833
[77]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,548
[78]M.J.S.Dewar,E.G.Zoebisch,E.F.Healy,Development and use of quantum mechanical molecular models..AMI:a new general purpose quantum mechanical molecular model,J.Am.Chem.Soc.,1985,107:3902-3909
[79]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,542-543
[80]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,506
[81]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,514
[82]李浩春,分析化学手册,第五分册(气相色谱分析),北京:化学工业出版社,1999,57