Congener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices

Abstract Chlorinated Paraffins (CPs) are high volume production chemicals and have been found in various organisms including humans and in environmental samples from remote regions. It is thus of great importance to understand the physical–chemical properties of CPs. In this study, gas chromatograph...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Jort Hammer, Hidenori Matsukami, Satoshi Endo
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/deba771ea3bc4194a063120da9482ee0
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:deba771ea3bc4194a063120da9482ee0
record_format	dspace
spelling	oai:doaj.org-article:deba771ea3bc4194a063120da9482ee02021-12-02T13:34:32ZCongener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices10.1038/s41598-021-84040-z2045-2322https://doaj.org/article/deba771ea3bc4194a063120da9482ee02021-02-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-84040-zhttps://doaj.org/toc/2045-2322Abstract Chlorinated Paraffins (CPs) are high volume production chemicals and have been found in various organisms including humans and in environmental samples from remote regions. It is thus of great importance to understand the physical–chemical properties of CPs. In this study, gas chromatographic (GC) retention indexes (RIs) of 25 CP congeners were measured on various polar and nonpolar columns to investigate the relationships between the molecular structure and the partition properties. Retention measurements show that analytical standards of individual CPs often contain several stereoisomers. RI values show that chlorination pattern have a large influence on the polarity of CPs. Single Cl substitutions (–CHCl–, –CH2Cl) generally increase polarity of CPs. However, many consecutive –CHCl– units (e.g., 1,2,3,4,5,6-C11Cl6) increase polarity less than expected from the total number of –CHCl– units. Polyparameter linear free energy relationship descriptors show that polarity difference between CP congeners can be explained by the H-bond donating properties of CPs. RI values of CP congeners were predicted using the quantum chemically based prediction tool COSMOthermX. Predicted RI values correlate well with the experimental data (R2, 0.975–0.995), indicating that COSMOthermX can be used to accurately predict the retention of CP congeners on GC columns.Jort HammerHidenori MatsukamiSatoshi EndoNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-11 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Jort Hammer Hidenori Matsukami Satoshi Endo Congener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices
description	Abstract Chlorinated Paraffins (CPs) are high volume production chemicals and have been found in various organisms including humans and in environmental samples from remote regions. It is thus of great importance to understand the physical–chemical properties of CPs. In this study, gas chromatographic (GC) retention indexes (RIs) of 25 CP congeners were measured on various polar and nonpolar columns to investigate the relationships between the molecular structure and the partition properties. Retention measurements show that analytical standards of individual CPs often contain several stereoisomers. RI values show that chlorination pattern have a large influence on the polarity of CPs. Single Cl substitutions (–CHCl–, –CH2Cl) generally increase polarity of CPs. However, many consecutive –CHCl– units (e.g., 1,2,3,4,5,6-C11Cl6) increase polarity less than expected from the total number of –CHCl– units. Polyparameter linear free energy relationship descriptors show that polarity difference between CP congeners can be explained by the H-bond donating properties of CPs. RI values of CP congeners were predicted using the quantum chemically based prediction tool COSMOthermX. Predicted RI values correlate well with the experimental data (R2, 0.975–0.995), indicating that COSMOthermX can be used to accurately predict the retention of CP congeners on GC columns.
format	article
author	Jort Hammer Hidenori Matsukami Satoshi Endo
author_facet	Jort Hammer Hidenori Matsukami Satoshi Endo
author_sort	Jort Hammer
title	Congener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices
title_short	Congener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices
title_full	Congener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices
title_fullStr	Congener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices
title_full_unstemmed	Congener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices
title_sort	congener-specific partition properties of chlorinated paraffins evaluated with cosmotherm and gas chromatographic retention indices
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/deba771ea3bc4194a063120da9482ee0
work_keys_str_mv	AT jorthammer congenerspecificpartitionpropertiesofchlorinatedparaffinsevaluatedwithcosmothermandgaschromatographicretentionindices AT hidenorimatsukami congenerspecificpartitionpropertiesofchlorinatedparaffinsevaluatedwithcosmothermandgaschromatographicretentionindices AT satoshiendo congenerspecificpartitionpropertiesofchlorinatedparaffinsevaluatedwithcosmothermandgaschromatographicretentionindices
_version_	1718392826213957632

Congener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices

Ejemplares similares