Supporting information. Influence of Aerosol Acidity on the Chemical Composition of Secondary Organic Aerosol from β caryophyllene
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1 Supporting information Influence of Aerosol Acidity on the Chemical Composition of Secondary Organic Aerosol from β caryophyllene M. N. Chan 1, J. D. Surratt 2,*, A. W. H. Chan 2,**, K. Schilling 2, J. H. Offenberg 3, M. Lewandowski 3, E. O. Edney 3, T. Kleindienst 3, M. Jaoui 4, E.S. Edgerton 5, R. L. Tanner 6, S. L. Shaw 7, M. Zheng 8, E. M. Knipping 9, J.H. Seinfeld 1,2 1 Division of Engineering and Applied Science, California Institute of Technology, Pasadena, California, USA. 2 Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California, USA. 3 National Exposure Research Laboratory, Human Exposure Atmospheric Sciences Division, United States Environmental Protection Agency, Research Triangle Park, North Carolina, USA. 4 Alion Science and Technology, P.O. Box 12313, Research Triangle Park, North Carolina, USA. 5 Atmospheric Research and Analysis, Inc., Cary, North Carolina, USA. 6 Environmental Technologies, Tennessee Valley Authority, Muscle Shoals, Alabama, USA. 7 Electric Power Research Institute, Palo Alto, California, USA. 8 School of Earth and Atmospheric Sciences, Georgia Institute of Technology, Atlanta, Georgia, USA. 9 Electric Power Research Institute, Washington, DC, USA. *Present address: Department of Environmental Science and Engineering, University of North Carolina at Chapel Hill, North Carolina, USA **Present address: Department of Environmental Science, Policy and Management, University of California, Berkeley, California, USA To whom correspondence should be addressed: J.H. Seinfeld (seinfeld@caltech.edu) 1
2 Table S1. β-caryophyllene products observed both in the series of β-caryophyllene/nox irradiation experiments and in fine ambient aerosol collected in downtown Atlanta, GA (JST) and a rural location in Yorkville, GA (YRK) during the 2008 AMIGAS Campaign a [M+H] + [M+Na] + [M+CH3OH+Na] + Compound Sample RT b Formula Measured Theoretical mda Formula Measured Theoretical mda Formula Measured Theoretical mda Concentration d β-nocaryophyllon aldehyde Experiment C14H23O C14H22O3Na C15H26O4Na (C14H22O3) JST D (+) JST N JST D JST N YRK D n.d. YRK N n.d. YRK D YRK N β-hydroxynocaryophyllon aldehyde Experiment C14H23O C14H22O4Na C15H26O5Na (C14H22O4) JST D a(+) JST N JST D JST N YRK D YRK N YRK D YRK N C15H24O4 Experiment C15H25O C15H24O4Na n.d. 268(+) n.d. JST D n.d n.d. 1.2 JST N n.d n.d. 1.6 JST D n.d n.d. 1.5 JST N n.d n.d. 1.5 YRK D n.d n.d. 1.3 YRK N n.d n.d. 1.2 YRK D n.d n.d. 2.0 YRK N n.d n.d. 1.6 β-dihydroxynocaryophyllon aldehyde Experiment C14H23O C14H22O5Na C15H26O6Na (C14H22O5) c JST D (+) JST N n.d. JST D JST N n.d. YRK D YRK N YRK D YRK N n.d. 2
3 n.d. = adduct ions are not detected; a Day (10 a.m. to 6 p.m., local time) and night (10 p.m. to 6 a.m., local time); b RT = retention time; c Weak signal intensity observed for ambient samples; GF 14 sample is chosen as an example; d Concentration is expressed in term of the intensity of ion normalized by the sampling air volume (ion intensity/m 3 ) in the AMIGAS samples. 3
4 Table S2. UPLC/ESI-TOFMS data for s detected by ESI in the positive ion mode in the series of β -caryophyllene/nox irradiation experiments. Data are obtained from Experiment 4. Suggested Retention [M+H] + [M+H] + [M+Na] + [M+Na] + [M+CH3+OH+Na] + [M+CH3+OH+Na] + ESI(+) Error Error Error chemical time Measured Theoretical Measured Theoretical Measured Theoretical (name) (mda) (mda) (mda) formula 184(+) C10H26O (+) C14H22O (β-nocaryophyllon aldehyde) 250(+) C15H22O (β -oxocaryophyllon aldehyde) 252a(+) C14H20O (β -oxonocaryophyllon aldehyde) 252b(+) C15H24O (β -hydroxycaryophyllon aldehyde) N253(+) C14H23NO a(+) C14H22O (β -hydroxynocaryophyllon aldehyde) b(+) C15H26O N267(+) C15H25NO (+) C15H24O (+) C14H22O (β -dihydroxynocaryophyllon aldehyde) 298(+) C15H22O
5 Table S3. UPLC/ESI-TOFMS data for s detected by ESI in the negative ion mode in the series of β -caryophyllene/nox irradiation experiments. Data are obtained from Experiment 4. Name Suggested chemical formula Measured Theoretical 186(-) C9H14O (-) C10H16O a(-) C14H20O b(-) β-caryophyllonic acid C15H24O (-) β-nocaryophyllonic acid / β-caryophyllinic acid C14H22O a(-) β-hydroxynornocaryophyllonic acid C13H20O b(-) Hydrated β-norcaryophyllonic acid C14H24O (-) β-oxocaryophyllonic acid C15H22O a(-) β-oxonocaryophyllonic acid C14H20O b(-) β-hydroxycaryophyllonic acid C15H24O a(-) β-hydroxynocaryophyllonic acid C14H22O b(-) Hydratedβ-caryophyllonic acid C15H26O (-) Hydrated β-nocaryophyllonic acid C14H24O (-) Hydrated β-oxocaryophyllonic acid C15H24O
6 Table S3 (Continued). UPLC/ESI-TOFMS data for s detected by ESI in the negative ion mode in the series of β -caryophyllene/nox irradiation experiments. Data are obtained from Experiment 4. Name Suggested chemical formula Measured Theoretical 286a(-) β-dihydroxynocaryophyllonic acid C14H22O b(-) Hydrated β-hydroxycaryophyllonic acid C15H26O (-) C17H26O (-) C13H28O a(-) C15H22O b(-) C16H26O (-) C14H24O (-) C17H28O a(-) C16H26O b(-) C17H30O
7 Table S4. UPLC/ESI-TOFMS data for s detected by ESI in the negative ion mode in the series of β -caryophyllene/nox irradiation experiments (nitrogen-containing s). Data are obtained from Experiment 4. Suggested chemical formula Measured Theoretical N195(-) C10H13NO N345(-) C16H27NO N347(-) C15H25NO N349a(-) C14H23NO N349b(-) C15H27NO N350(-) C13H22N2O N363a(-) C15H25NO N363b(-) C16H29NO N375(-) C17H29NO N546(-) C24H38N2O C12H19NO6 (monomer)
8 Table S5. UPLC/ESI-TOFMS data for s detected by ESI in the negative ion mode in the series of β -caryophyllene/nox irradiation experiments (organosulfates). Data are obtained from Experiment 4. Suggested chemical formula Measured Theoretical S252(-) C9H16O6S S304(-) C14H24O5S S318(-) C15H26O5S S320(-) C14H24O6S S334a(-) C14H22O7S S334b(-) C15H26O6S S348(-) C15H24O7S S350a(-) C14H22O8S S350b(-) C15H26O7S S352(-) C14H24O8S
9 Table S5 (Continued). UPLC/ESI-TOFMS data for s detected by ESI in the negative ion mode in the series of β -caryophyllene/nox irradiation experiments (organosulfates). Data are obtained from Experiment 4. Suggested chemical formula Measured Theoretical S364a(-) C15H24O8S S364b(-) C16H28O7S S380(-) C16H28O8S Nitrated Organosulfates S363(-) C15H25NO7S S383(-) C14H25NO9S
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