Supplemental data: Tran B. Nguyen, Sergey A. Nizkorodov, Alexander Laskin, and Julia Laskin

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1 Supplemental data: An approach toward quantification of organic compounds in complex environmental samples using high-resolution electrospray ionization mass spectrometry Tran B. Nguyen, Sergey A. Nizkorodov, Alexander Laskin, and Julia Laskin Table S1: Compounds used for statistical analysis in manuscript and their accompanying physical properties. Compounds are sorted by molecular mass. Data were taken from Ref 1 and references therein. Heterocyclic Nitrogen (Imidazoles) R N N R 2 R 1 Adj. mass PA GB (Da) H/C (Da) (kj/mol) (kj/mol) Imidazole Methyl-1H-imidazole Methyl-1H-imidazole ,4-Dimethyl-1H-imidazole ,2-Dimethyl-1H-imidazole ,5-Dimethyl-1H-imidazole H-Benzimidazole Methyl-1H-benzimidazole Molecular Volume (Å 3 ) Heterocyclic Nitrogen (Pyrazoles) HN N R R Adj. mass PA GB R 1 (Da) H/C (Da) (kj/mol) (kj/mol) 1H-Pyrazole Methyl-1H-pyrazole Methyl-1H-pyrazole Methyl-1H-pyrazole ,3-Dimethyl-1H-pyrazole ,5-Dimethyl-1H-pyrazole ,4-Dimethyl-1H-pyrazole ,5-Dimethyl-1H-pyrazole ,3,5-Trimethyl-1H-pyrazole ,4,5-Trimethyl-1H-pyrazole Methyl-3-phenyl-1H-pyrazole Methyl-5-phenyl-1H-pyrazole ,5-Diphenyl-1H-pyrazole Molecular Volume (Å 3 )

2 R 1 2 R R 3 Pyridines R N R 4 Pyridine Methylpyridine Methylpyridine Methylpyridine Vinylpyridine Ethylpyridine Ethylpyridine Ethylpyridine ,3-Dimethylpyridine ,4-Dimethylpyridine ,5-Dimethylpyridine ,6-Dimethylpyridine ,4-Dimethylpyridine ,5-Dimethylpyridine Isopropylpyridine Propylpyridine ,6-Diethylpyridine tert-Butylpyridine tert-Butylpyridine Phenylpyridine Hexylpyridine ,4-Di-tert-butylpyridine ,6-Di-tert-butylpyridine O R 1 Saturated Esters R O Methylformate Ethylformate Methylacetate Propylformate Isopropylformate Ethylacetate Methylpropanoate Butylformate Propylacetate Isopropylacetate Methylbutanoate Methylisobutanoate Methyl2,2-dimethylpropanoate

3 Methylcyclohexanecarboxylate Methylcyclopropanecarboxylate O Unsaturated R Esters Ph O Methyltrans-2-butenoate Methylbenzoate Methyl2-methylbenzoate Methyl3-methylbenzoate Methyl4-methylbenzoate Methyl4-hydroxybenzoate Methyl3-hydroxybenzoate Methyl4-formylbenzoate Methyl4-methoxybenzoate Methyl3-methoxybenzoate Methyl2,5-dimethylbenzoate Methyl2,4-dimethylbenzoate Methyl3,5-dimethylbenzoate Methyl2,4,6-trimethylbenzoate Dimethylterephthalate Dimethylisophthalate Acetylphenylacetate Vinylacetate Methylacrylate Methylmethacrylate O Alkyl Ethers R R 1 Dimethylether Ethylmethylether Dipentylether Diethylether Methylpropylether Butyl methylether Methyltert-butylether Ethylisopropylether Isopropylmethylether tert-butylethylether tert-butylisopropylether Dipropylether Diisopropylether Dibutylether Di-sec-butylether

4 Di-tert-butylether O Saturated Ketones R R 1 5-Nonanone Di-tert-butylketone ,4-Dimethyl-3-pentanone ,3-Dimethyl-2-butanone ,2,4-Trimethyl-3-pentanone Butanone Pentanone Pentanone Methyl-2-butanone Hexanone Heptanone Acetone Cyclobutanone Cyclopentanone Cyclohexanone Cycloheptanone Methylcyclohexanone Cyclooctanone Cyclohexylethanone Cyclononanone NH 2 R 1 R NH Diamines 2 1,2-Ethanediamine ,3-Propanediamine ,4-Butanediamine ,5-Pentanediamine ,2-Benzenediamine ,3-Benzenediamine ,4-Benzenediamine Triethylenediamine ,6-Hexanediamine ,7-Heptanediamine ,8-Naphthalenediamine Primary Amines R NH 2 (Da) H/C Adj. mass (Da) PA (kj/mol) GB (kj/mol) Molecular Volume (Å 3 )

5 Methylamine Ethylamine Cyclopropylamine Propylamine Isopropylamine Butylamine tert-butylamine Isobutylamine Pentylamine Cyclohexylamine Hexylamine Benzylamine Heptylamine Octylamine Cyclohexanemethanamine ,2-Dimethylpropylamine NH Secondary Amines R R 1 Dimethylamine Diethylamine Isopropylmethylamine Allyldimethylamine Methyl-2-butanamine Ethylisopropylamine Dipropylamine Diisopropylamine Dibutylamine Di-sec-butylamine Diisobutylamine R 1 Tertiary Amines R N R 2 Trimethylamine Ethyldimethylamine Diethylmethylamine Butyldimethylamine Isobutyldimethylamine Triethylamine Methyldipropylamine Diethylpropylamine Cyclohexyldimethylamine

6 Tripropylamine Tributylamine R OH Alcohols Methanol Ethanol Propanol Propanol Butanol Butanol Methyl-1-propanol Methyl-2-propanol ,2-Dimethyl-1-propanol Cyclohexanemethanol O Carboxylic Acids R OH Formic acid Acetic acid Propanoic acid Methacrylic acid Cyclopropanecarboxylic acid Methyl-2-butenoic acid cis-2-methyl-2-butenoic acid Cyclobutanecarboxylic acid Cyclopentanecarboxylic acid Benzoic acid Cyclohexanecarboxylic acid Toluic acid

7 Table S2: Hydrocarbons and oxygenated hydrocarbon compounds used for statistical analysis in Fig. 7 in the manuscript and their accompanying average polarizability values. Compounds are sorted by number of carbon. Data were taken from Ref 2 and references therein. Hydrocarbons C H O H/C AM Polarizability (10 24 cm 3 ) methane acetylene ethylene ethane propyne propene cyclopropane propane butyne ,3-butadiene butene trans-2-butene methylpropene butane isobutane ,3-cyclopentadiene pentyne trans-1,3-pentadiene isoprene cyclopentane pentene pentene pentane neopentane benzene hexyne ethyl-1,3-butadiene methyl-1,3-pentadiene methyl-1,3-pentadiene ,3-dimethyl-1,3-butadiene cyclohexene cyclohexane hexene hexane toluene heptyne methylcyclohexane heptene

8 heptane styrene ethylbenzene o-xylene p-xylene m-xylene ethylcyclohexane n-octane methylheptane ,2,4-trimethylpentane a-methylstyrene isopropylbenzene ,3,5-trimethylbenzene isopropylcyclohexane nonane naphthalene durene tert-butylbenzene tert-butylcyclohexane decane a-methylnaphthalene ß-methylnaphthalene Oxygenated hydrocarbons C H O H/C AM Polarizability ethyleneglycol propenal acetone allylalcohol propionaldehyde propionicacid ethylformate methylacetate dimethylcarbonate propanol propanol ethylmethylether dimethoxymethane ethyleneglycolmonomethylether diketene crotonaldehyde methacrylaldehyde biacetyl aceticanhydride butanal

9 methylethylketone trans-2,3-epoxybutane ethylacetate ,4-dioxane p-dioxane methyl-1,3-dioxolane butyricacid methylpropionate ethylether butanol methylpropanol methylpropylether ethyleneglycolmonoethylether acetylacetone diethylketone methylpropylketone ethylpropionate methylbutanoate diethylcarbonate ethylpropylether tetramethylorthocarbonate phenol ethylacetoacetate cyclohexanol amylformate paraldehyde propylether ,1-diethoxyethane ,2-diethoxyethane anisole cyclohexylmethylether ,4-dimethyl-3-pentanone pentylacetate acetophenone phenetole ethylsorbate tetramethylcyclobutane-1,3-dione diethylsuccinate butylether ethylbenzoate naphthaldehyde naphthaldehyde

10 References: 1. E. P. L. Hunter and S. G. Lias, J. Phys. Chem. Ref. Data, 1998, 27, T. M. Miller, ed., Atomic and molecular polarizabililies, 92 edn., CRC Press, Boca Raton, FL., 2012.