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Semi‐empirical topological index to predict properties of halogenated aliphatic compounds
Author(s) -
Arruda Anna Celia Silva,
Junkes Berenice da Silva,
Souza Érica Silva,
Yunes Rosendo Augusto,
Heinzen Vilma Edite Fonseca
Publication year - 2008
Publication title -
journal of chemometrics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.47
H-Index - 92
eISSN - 1099-128X
pISSN - 0886-9383
DOI - 10.1002/cem.1121
Subject(s) - boiling point , correlation coefficient , topological index , chemistry , polynomial , melting point , linear regression , coefficient of determination , analytical chemistry (journal) , mathematics , thermodynamics , chromatography , organic chemistry , statistics , computational chemistry , mathematical analysis , physics
This study was carried out to show the predictive capacity of the semi‐empirical topological index ( I ET ) in estimating some important physical properties; melting point, Mp (°C), boiling point, Bp (°C), and experimental log p of halogenated aliphatic hydrocarbons. The retention index (RI) values of 141 compounds were used in the building of this specific model of the I ET . The simple linear regression between RI Exp and the I ET exhibits high quality with a coefficient of determination of r 2 = 0.9995, standard deviation of SD = 8 and leave‐one‐out cross‐validation correlation coefficient of $r_{{\bf cv}}^2 $ = 0.999. The best correlations between experimental melting, Mp (°C), and boiling Bp (°C) points, and I ET were achieved through quadratic polynomial equations. The correlation of Bp (°C) with I ET for 86 compounds showed excellent results: r 2 = 0.9971, SD = 4.2, $r_{{\bf cv}}^2 $ = 0.997. From this equation the values of 24 compounds not included in the model were calculated ( r 2 = 0.9931; SD = 7.6). The correlation between Mp (°C) and I ET for 43 compounds was very good ( r 2 = 0.9865; SD = 6.1; $r_{{\bf cv}}^2 $ = 0.985), and experimental values of eight compounds not included in the initial model also showed good correlation with calculated values ( r 2 = 0.9903; SD = 4.1). Finally, for 19 compounds the correlation between the experimental log p ‐value and that calculated using the I ET method gave a value of r 2 = 0.9871, while the correlation with the value obtained using the most used Fragment Addition Method was r 2 = 0.9750. These results show the predictive capacity of the I ET for these physical properties. Copyright © 2008 John Wiley & Sons, Ltd.