Predicting thermochemical parameters of oxygen-containing heterocycles using simple QSPR models

References

• Penczek , S. 2000 . Cationic ring-opening polymerization (CROP) major mechanistic phenomena . J. Polym. Sci. A , 38 : 1919
   Web of Science ®Google Scholar
• Baccarelli , A. , Mocarelli , P. , Patterson , D.G. Jr , Bonzini , M. , Pesatori , A.C. , Caporaso , N. and Landi , M.T. 2002 . Immunologic effects of dioxin: new results from seveso and comparison with other studies . Environ. Health Perspect , 110 : 1169
   PubMed Web of Science ®Google Scholar
• Cramail , H. and Deffieux , A. 1999 . “ Cationic polymerization ” . In Synthesis of Polymers , Edited by: Schlueter , A.D. 231 Weinheim : Wiley-VCH .
   Google Scholar
• E. Brock. Asia—future market for engineering plastics, http://www.ticona.com/ticona/ed_brock_16_6_uk_pdf.pdf (accessed November 2005).
   Google Scholar
• BASF, Press Release. Available online at: http://media.basf.com/en/presse/mitteilungen/pm.htm?pmid=1761&id=c0P1t7gw7bcp0oS (accessed November 2005).
   Google Scholar
• Benson , S.W. 1976 . Thermochemical Kinetics , New York : John Wiley & Sons .
   Google Scholar
• Benson , S.W. and Buss , J.H. 1958 . Additivity rules for the estimation of molecular properties. Thermodynamic properties . J. Chem. Phys. , 29 : 546
   Web of Science ®Google Scholar
• Benson , S.W. , Cruickshank , F.R. , Golden , D.M. , Haugen , G.R. , O'Neal , H.E. , Rodgers , A.S. , Shaw , R. and Walsh , R. 1969 . Additivity rules for the estimation of thermochemical parameters . Chem. Rev. , 69 : 279
   Web of Science ®Google Scholar
• Saito , N. and Fuwa , A. 2000 . Prediction for thermodynamic function of dioxins for gas phase using semiempirical molecular orbital method with PM3 Hamiltonian . Chemosphere , 40 : 131
   PubMedGoogle Scholar
• Wilcox , C.F. , Zhang , Y.-X. and Bauer , S.H. 2001 . The thermochemistry of TNAZ (1,3,3-trinitroazetidine) and related species: G3(MP2)//B3LYP heats of formation . J. Mol. Struct.: Theochem. , 538 : 67
   Google Scholar
• Notario , R. , Roux , M.V. and Castano , O. 2001 . The enthalpy of formation of dibenzofuran and some related oxygen containing heterocycles in the gas phase . Phys. Chem. Chem. Phys. , 3 : 3717
   Google Scholar
• Ahunbay , M.G. , Kranias , S. , Lachet , V. and Ungerer , P. 2004 . Prediction of thermodynamic properties of heavy hydrocarbons by Monte Carlo simulations . Fluid Phase Equilib. , 224 : 73
   Web of Science ®Google Scholar
• Stewart , J.J.P. 1989 . Optimization of parameters for semiempirical methods I. Method . J. Comput. Chem. , 10 : 209
   Web of Science ®Google Scholar
• Stewart , J.J.P. 1989 . Optimization of parameters for semiempirical methods II. Applications . J. Comput. Chem. , 10 : 221
   Web of Science ®Google Scholar
• Lay , T.S. , Yamada , T. , Tsai , P.-L. and Bozelli , J.W. 1997 . Thermodynamic parameters and group additivity ring corrections for three-to-six-membered oxygen heterocyclic hydrocarbons . J. Phys. Chem. B , 101 : 2471
   Google Scholar
• Lay , T.S. and Bozzelli , J.W. 1997 . Enthalpies of formation and group additivity of alkyl peroxides and trioxides . J. Phys. Chem. A , 101 : 9505
   Web of Science ®Google Scholar
• Lay , T.S. and Bozzelli , J.W. 1997 . Enthalpies of formation of cyclic alkyl peroxides: dioxirane, 1,2-dioxetane, 1,2-dioxolane and 1,2-dioxane . Chem. Phys. Lett. , 268 : 175
   Google Scholar
• Shirel , M.L. and Pulay , P. 1999 . Stability of novel oxo- and chloro-substituted trioxanes . J. Am. Chem. Soc. , : 121
   Google Scholar
• Li , X.-W. , Shibata , E. and Nakamura , T. 2003 . Theoretical calculation of thermodynamic properties of polybrominated dibenzo-p-dioxins . J. Chem. Eng. Data , 48 : 727
   Google Scholar
• Delley , J. 1990 . An all-electron numerical method for solving the local density functional for polyatomic molecules . J. Chem. Phys. , 92 : 508
   Web of Science ®Google Scholar
• Delley , J. 2000 . From molecules to solids with the DMol3 approach . J. Chem. Phys. , 113 : 7756
   Web of Science ®Google Scholar
• Hammer , B. , Hansen , L.B. and Norskov , J.K. 1999 . Improved adsorption energetics within density-functional theory using revised Perdew–Burke Ernzerhof functionals . Phys. Rev. B , 59 : 7413
   Web of Science ®Google Scholar
• Becke , A.D.J. 1988 . A multicenter numerical integration scheme for polyatomic molecules . J. Chem. Phys. , 88 : 2547
   Web of Science ®Google Scholar
• Lee , C. , Yang , W. and Parr , R.G. 1988 . Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density . Phys. Rev. B , 37 : 785
   PubMed Web of Science ®Google Scholar
• Boese , A.D. and Handy , N.C. 2001 . A new parametrization of exchange-correlation generalized gradient approximation functionals . J. Chem. Phys. , 114 : 5497
   Web of Science ®Google Scholar
• Rauhut , G. and Clark , T. 1993 . Multicenter point charge model for high-quality molecular electrostatic potentials from AM1 calculations . J. Comput. Chem. , 15 : 503
   Google Scholar
• Beck , B. , Rauhut , G. and Clark , T. 1994 . The natural atomic orbital point charge model for PM3: multipole moments and molecular electrostatic potentials . J. Comput. Chem. , 15 : 1064
   Web of Science ®Google Scholar
• Accelrys. homepage, Available online at: http://www.accelrys.com (accessed November 2005).
   Google Scholar
• National Institute of Standards, Chemistry Webbook, Available online at: http://webbook.nist.gov/chemistry (accessed November 2005).
   Google Scholar
• Reid , R.C. , Prausnitz , J.M. and Poling , B.E. 1987 . The Properties of Gases and Liquids , London : MacGraw-Hill Book Company .
   Google Scholar
• Lyman , W.J. , Reehl , W.F. and Rosenblatt , D.H. 1982 . “ Environmental behaviour of environmental compounds ” . In Handbook of Chemical Property Estimation Methods , London : McGraw-Hill Book Company .
   Google Scholar
• R.D. Johnson III. NIST computational chemistry comparison and benchmark database, NIST standard reference database number 101, Available online at: http://srdata.nist.gov/ccbdb (accessed November 2005).
   Google Scholar
• Rogers , D. and Hopfinger , A.J. 1994 . Application of genetic function approximation in quantitative structure-activity relationships and quantitative structure-property relationships . J. Chem. Inf. Comput. Sci. , 34 : 854
   Google Scholar
• Senese , C.L. and Hopfinger , A.J. 2003 . A simple clustering technique to improve QSAR model selection and predictivity: application to a receptor independent 4D-QSAR analysis of cyclic urea derived inhibitors of HIV-1 protease . J. Chem. Inf. Comput. Sci. , 43 : 2180
   PubMedGoogle Scholar
• Yasri , A. and Hartsough , D. 2001 . Toward an optimal procedure for variable selection and QSAR model building . J. Chem. Inf. Comput. Sci. , 41 : 1218
   PubMedGoogle Scholar
• Wu , W. , Walczak , B. , Massart , D.L. , Heuerding , S. , Erni , F. , Last , I.R. and Prebble , K.A. 1996 . Artificial neural networks in classification of NIR spectral data: design of the training set . Chemom. Intell. Lab. Syst. , 33 : 35
   Web of Science ®Google Scholar
• Poetter , T. and Matter , H. 1990 . Random or rational design? Evaluation of diverse compound subsets from chemical structure databases . J. Med Chem. , 41 : 478
   Google Scholar
• Golbraikh , A. and Tropsha , A. 2002 . Predictive QSAR modeling based on diversity sampling of experimental datasets for the training and test set selection . J. Comput. Aided Mol. Des. , 16 : 357
   PubMed Web of Science ®Google Scholar
• Kauffman , G.V. and Jurs , P.C. 2001 . QSAR and k-nearest neighbour classification analysis of selective cyclooxygenase-2 inhibitors using topologically based numerical descriptors . J. Chem. Inf. Comput. Sci. , 41 : 1553
   PubMedGoogle Scholar
• Mattioni , B.E. and Jurs , P.C. 2002 . Development of quantitative structure-activity relationship and classification models for a set of carbonic anhydrase inhibitors . J. Chem. Inf. Comput. Sci. , 42 : 94
   PubMedGoogle Scholar
• Guha , R. , Serra , J.R. and Jurs , P.C. 2004 . Generation of QSAR sets with a self-organizing map . J. Mol. Graph. Model , 23 : 1
   PubMed Web of Science ®Google Scholar
• Bayram , E. , Santago , P. , Harris , R. , Xiao , Y.-D. , Clauset , A.J. and Schmitt , J.D. 2004 . Genetic algorithms and self-organizing maps: a powerful combination for modeling complex QSAR and QSPR problems . J. Comput. Aided Mol. Des. , 18 : 483
   PubMed Web of Science ®Google Scholar
• Sjostrom , M. and Eriksson , L. 1995 . “ Applications of statistical experimental design ” . In Chemometrics Methods in Molecular Design , Edited by: van de Waterbeed , H. 63 Weinheim : VCH .
   Google Scholar
• Eriksson , L. and Johansson , E. 1996 . Multivariate design and modeling in QSAR . Chemom. Intell. Lab. Syst. , 34 : 1
   Web of Science ®Google Scholar
• Gramatica , P. and Papa , E. 2003 . QSAR Modeling of bioconcentration factor by theoretical molecular descriptors . QSAR Comb. Sci. , 22 : 374
   Google Scholar
• Gramatica , P. , Pilutti , P. and Papa , E. 2003 . QSAR prediction of ozone tropospheric degradation . QSAR Comb. Sci. , 22 : 364
   Google Scholar
• Marengo , E. and Todeschini , R. 1992 . A new algorithm for optimal, distance-based experimental design . Chemom. Intell. Lab. Sys. , 16 : 37
   Web of Science ®Google Scholar
• Montgomery , D.C. 2001 . Design and Analysis of Experiments , New York : John Wiley .
   Google Scholar
• Tropsha , A. , Grammatica , P. and Gombar , V.K. 2003 . The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models . QSAR Comb. Sci. , 22 : 69
   Google Scholar
• Accelrys, Accelrys MS modeling 3.2 documentation. (2005).
   Google Scholar
• Hall , L.H. , Mohney , B. and Kier , L.B. 1991 . The electrotopological state: structure information at the atomic level for molecular graphs . J. Chem. Inf. Comput. Sci. , 31 : 76
   Google Scholar
• Hansch , C. , Garg , R. and Kurup , A. 2001 . Searching for Allosteric Effects via QSARs . Bioorg. Med. Chem. , 9 : 283
   PubMedGoogle Scholar
• Hall , L.H. and Kier , L.B. 1992 . “ The molecular connectivity chi indexes and kappa shape indexes in structure property modeling ” . In Reviews in Computational Chemistry Edited by: Lipkovitz , K.B. and Boyd , D.B.
   Google Scholar
• Colmont , J.-M. 1980 . Assignment method of the rotational spectrum of a slightly asymmetric molecule . J. Molec. Spec. , 80 : 166
   Google Scholar