Correspondence pubs.acs.org/IECR
Comment on “Group Contribution-Based Method for Determination of Solubility Parameter of Nonelectrolyte Organic Compounds” and “Solubility Parameters of Nonelectrolyte Organic Compounds: Determination Using Quantitative Structure−Property Relationship Strategy” Sierra Rayne* Chemologica Research, PO Box 74, 318 Rose Street, Mortlach, Saskatchewan S0H 3EO, Canada n their article, Gharagheizi et al.1 “propose a predictive method based on the combination of the Group Contribution strategy with the Artificial Neural Network to calculate/estimate the solubility parameter values of about 1620 nonelectrolyte organic compounds at 298.15 K and atmospheric pressure. The chemical functional groups are obtained for various compounds categorized in 81 different chemical families.” Unfortunately, a large number of the 1620 purportedly “nonelectrolyte organic compounds” investigated by these authors are not organic compounds and/or are electrolytes. In the Supporting Information from ref 1, the authors provide a numbered list of their 1620 compounds with corresponding names, molecular formulas, CAS RN, and the chemical “family” to which each compound belongs. Using their numbering/naming system (presented as number [name]), the following compounds claimed to be “organic compounds” by Gharagheizi et al.1 are, in fact, inorganic compounds: 382 (carbon dioxide), 383 (nitric oxide; also incorrectly drawn with a H atom attached in ref 1), 384 (fluorine), 385 (chlorine), 386 (arsine), 929 (hydrogen cyanide), 1047 (sulfuric acid), 1048 (phosphoric acid), 1049 (nitric acid), 1050 (hydrogen fluoride), 1051 (hydrogen bromide), 1052 (hydrogen iodide), 1053 (ammonia), 1054 (phosphorus trichloride), 1055 (phosphorus oxychloride), 1056 (dichlorosilane), 1057 (trichlorosilane), 1058 (tetrachlorosilane), 1059 (carbon disulfide), 1060 (sulfur hexafluoride), 1061 (boron trifluoride), 1062 (sulfuryl chloride), 1063 (thionyl chloride), 1064 (boron trichloride), 1067 (tetrafluorosilane), 1070 (nitrogen trifluoride), 1075 (nitrosyl chloride), 1360 (fluorosulfonic acid), 1361 (chlorosulfonic acid), 1362 (chlorine dioxide; which is also incorrectly drawn as having a H atom attached in ref 1), 1363 (perchloric acid), 1489 (tin(IV) chloride), 1498 (sulfur dichloride), and 1499 (hydrogen selenide). The following compounds are organometallic: 1020 (triisobutyl aluminum), 1065 (hexamethyldisilazane), 1066 (hexamethyldisiloxane), 1068 (dodecamethylpentasiloxane), 1069 (methyl vinyl dichlorosilane), 1071 (bis[3(triethoxysilyl)propyl]disulfide), 1072 (disilane), 1073 (silane), 1074 (tetramethylsilane), 1076 (octamethylcyclotetrasiloxane), 1364 (octamethyltrisiloxane), 1365 (octadecamethyloctasiloxane), 1366 (tetraethyl silane), 1367 (hexadecamethylheptasiloxane), 1487 (trimethyl indium), 1488 (triethyl gallium), 1490 (hexadecamethylcyclooctasiloxane), 1491 (eicosamethylnonasi-
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loxane), 1492 (hexacosamethyldodecasiloxane), 1493 ((3methylacryloxypropyl)trichlorosilane), 1494 (methyl chlorosilane), 1495 (methyl dichlorosilane), 1496 (methyl trichlorosilane), 1497 (vinyltrichlorosilane), 1500 (trimethylaluminum), 1501 (trimethylgallium), 1502 (tetraethyl lead), 1503 (bis[3-(trimethoxysilyl)propyl]disulfide), 1504 (trimethyl silane), 1505 (dimethylchlorosilane), 1506 (trimethylchlorosilane), 1507 (dimethyldichlorosilane), 1508 (decamethylcyclopentasiloxane), 1509 (dodecamethylcyclohexasiloxane), 1510 (diphenyldichlorosilane), 1511 (ethyltrichlorosilane), 1512 (dichlorodiethylsilane), 1544 (vinyltrimethoxysilane), 1545 (trimethoxysilane), 1546 (dimethyldimethoxysilane), 1547 (phenyltrichlorosilane), 1548 (phenylmethyldichlorosilane), 1549 (trimethyl silanol), 1550 (tetradecamethylhexasiloxane), and 1551 (decamethyltetrasiloxane). Several of these compounds are also electrolytes (e.g., those named “acids,” such as sulfuric, nitric, and phosphoric acids). Similarly, in ref 2, Gharagheizi et al. employed a quantitative structure−property relationship method in an attempt to predict the solubility parameters of purportedly “nonelectrolyte organic compounds”. Among the supposed “nonelectrolyte organic compounds” investigated in ref 2 and listed in the Supporting Information of this manuscript, the following compounds are not “organic compounds”: sulfuric acid, phosphoric acid, nitric acid, hydrogen fluoride, hydrogen bromide, hydrogen iodide, phosphorus trichloride, phosphorus oxychloride, tetrachlorosilane, carbon disulfide, boron trifluoride, sulfuryl chloride, thionyl chloride, fluosulfonic acid, and chlorosulfonic acid.
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AUTHOR INFORMATION
Corresponding Author
*Tel.: + (1) 306 690 0573. Fax: + (1) 306 690 0573. E-mail:
[email protected]. Notes
The authors declare no competing financial interest.
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REFERENCES
(1) Gharagheizi, F.; Eslamimanesh, A.; Mohammadi, A. H.; Richon, D. Group Contribution-Based Method for Determination of Solubility Parameter of Nonelectrolyte Organic Compounds. Ind. Eng. Chem. Res. 2011, 50, 10344−10349.
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dx.doi.org/10.1021/ie400117h | Ind. Eng. Chem. Res. 2013, 52, 3947−3948
Industrial & Engineering Chemistry Research
Correspondence
(2) Gharagheizi, F.; Eslamimanesh, A.; Farjood, F.; Mohammadi, A. H.; Richon, D. Solubility parameters of nonelectrolyte organic compounds: Determination using quantitative structure−property relationship strategy. Ind. Eng. Chem. Res. 2011, 50, 11382−11395.
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dx.doi.org/10.1021/ie400117h | Ind. Eng. Chem. Res. 2013, 52, 3947−3948
