resumo
N-(diethylaminothiocarbonyl)benzimido derivatives are polar multifunctional substances. A set of these compounds was synthesised by successive substitution on the enamine side, resulting in similar substances with different polarities, providing a set of model compounds with respect to the study of substituent effects on physico-chemical properties. Experimental aqueous solubility data, at T=298.15 K, of N-(diethylaminothiocarbonyl)benzamidine, PhCNH2NCSNEt2 (1),N-(diethylaminothiocarbonyl)-N'-phenylbenzamidine, PhCNHPhNCSNEt2 (2), N-(diethylaminothiocarbonyl)-N'-monoethylbenzamidine, PhCNHEtNCSNEt2 (3), N-(diethylaminothiocarbonyl)-N',N'-diethylbenzamidine, PhCNEt2NCSNEt2 (4), and N-(diethylaminothiocarbonyl)benzimido ethylester, PhCOEtNCSNEt2 (5) were measured at T = 298.15 K. The obtained data are supplemented by COSMO-RS aqueous solubility predictions as well as other environmentally important partition coefficients. This information is shown in a two-dimensional chemical space diagram, providing indications about the compartment into which the bulk of the compounds is likely to concentrate. The expected quality of COSMO-RS predictions for this type of screening exercise is illustrated on a set of pesticides with established thermophysical property data. (C) 2016 Elsevier Ltd. All rights reserved.
palavras-chave
COSMO-RS; PARTITION-COEFFICIENTS; N-ACYLTHIOUREAS; PREDICTION; BEHAVIOR; N-(THIOCARBAMOYL)BENZAMIDINES; CHLOROBENZENES; TAUTOMERISM; BENZAMIDINE; PERSISTENCE
categoria
Environmental Sciences & Ecology
autores
Schroder, B; Martins, MAR; Coutinho, JAP; Pinho, SP
nossos autores
Bernd Schroder
Bolseiro de pós-Doutoramento
Projectos
agradecimentos
Bernd Schroder acknowledges Fundacao para a Ciencia e a Tecnologia (FCT) and the European Social Fund (ESF) under the 3rd Community Support Framework (CSF) for the award of a postdoctoral grant (grant number SFRH/BPD/38637/2007) and the award of research project PTDC/AAC-AMB/121161/2010. This work was developed in the scope of the projects CICECO-Aveiro Institute of Materials (Ref. FCT UID/CTM/50011/2013) and LSRE-LCM Associate Laboratory (Project POCI-01-0145-FEDER-006984), financed by national funds through the FCT and by FEDER funds through COMPETE 2020-POCI. M.A.R.M thanks to FCT for financial support for the PhD grant SFRH/BD/87084/2012.