Revisiting shape selectivity in liquid chromatography for polycyclic aromatic hydrocarbons (PAHs) - six-ring and seven-ring Cata-condensed PAH isomers of molecular mass 328 Da and 378 Da

Jorge O Oña-Ruales; Lane C Sander; Walter B Wilson; Stephen A Wise

doi:10.1007/s00216-017-0456-x

Revisiting shape selectivity in liquid chromatography for polycyclic aromatic hydrocarbons (PAHs) - six-ring and seven-ring Cata-condensed PAH isomers of molecular mass 328 Da and 378 Da

Anal Bioanal Chem. 2018 Jan;410(3):885-896. doi: 10.1007/s00216-017-0456-x. Epub 2017 Jun 28.

Authors

Jorge O Oña-Ruales^{1

2}, Lane C Sander³, Walter B Wilson³, Stephen A Wise³

Affiliations

¹ Chemical Sciences Division, National Institute of Standards and Technology (NIST), 100 Bureau Dr. MS 8392, Gaithersburg, MD, 20899, USA. jorge.ona-ruales@alumni.lsu.edu.
² Department of Chemical Engineering, Nazarbayev University, Astana, Kazakhstan, 010000. jorge.ona-ruales@alumni.lsu.edu.
³ Chemical Sciences Division, National Institute of Standards and Technology (NIST), 100 Bureau Dr. MS 8392, Gaithersburg, MD, 20899, USA.

PMID: 28660336
DOI: 10.1007/s00216-017-0456-x

Abstract

The relationship of reversed-phase liquid chromatography (RPLC) retention on a polymeric C₁₈ stationary phase and the shape of polycyclic aromatic hydrocarbons (PAHs) was investigated for three-ring to seven-ring cata-condensed isomers. We report the first RPLC separation for six-ring and seven-ring cata-condensed PAH isomers. Correlations of LC retention and shape parameters (length-to-breath ratio, L/B and thickness, T) were investigated for 2 three-ring isomers (molecular mass 178 Da), 5 four-ring isomers (molecular mass 228 Da), 11 five-ring isomers (molecular mass 278 Da), 17 six-ring isomers (molecular mass 328 Da), and 20 seven-ring isomers (molecular mass 378 Da). Significant linear correlations were found for all isomer groups (r = 0.71 to 0.94). Nonplanarity of the PAH isomers was found to influence retention (i.e., nonplanar isomers eluting earlier than expected based on L/B) and linear correlations of retention vs. T for isomer groups containing nonplanar isomers were significant (r = 0.71 to 0.86). Graphical abstract.

Keywords: High molecular mass PAHs; Length-to-breadth ratio (L/B); Nonplanarity; Polycyclic aromatic hydrocarbons (PAHs); Reverse-phase liquid chromatography (RPLC); Shape selectivity.