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Terpenylic acid and related compounds from the oxidation of α-pinene: implications for new particle formation and growth above forests

(2009) ENVIRONMENTAL SCIENCE & TECHNOLOGY. 43(18). p.6976-6982
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Abstract
Novel secondary organic aerosol (SOA) products from the monoterpene a-pinene with unique dimer-forming properties have been identified as lactone-containing terpenoic acids, i.e., terpenylic and 2-hydroxyterpenylic acid, and diaterpenylic acid acetate. The structural characterizations were based on the synthesis of reference compounds and detailed interpretation of mass spectral data. Terpenylic acid and diaterpenylic acid acetate are early oxidation products generated upon both photooxidation and ozonolysis, while 2-hydroxyterpenylic acid is an abundant SOA tracer in ambient fine aerosol that can be explained by further oxidation of terpenylic acid. Quantum chemical calculations support that noncovalent dimer formation involving double hydrogen bonding interactions between carboxyl groups of the monomers is energetically favorable. The molecular properties allow us to explain initial particle formation in laboratory chamber experiments and are suggested to play a role in new particle formation and growth above forests, a natural phenomenon that has fascinated scientists for more than a century.
Keywords
NUCLEATION, ALPHA-PINENE/O-3 REACTION, EMISSIONS, CHEMISTRY, OZONOLYSIS, AB-INITIO, MASS-SPECTROMETRY, ATMOSPHERIC PARTICLES, SECONDARY ORGANIC AEROSOL, PRODUCTS

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Chicago
Claeys, Magda, Yoshiteru Iinuma, Rafal Szmigielski, Jason D Surratt, Frank Blockhuys, Christian Van Alsenoy, Olaf Boge, et al. 2009. “Terpenylic Acid and Related Compounds from the Oxidation of Α-pinene: Implications for New Particle Formation and Growth Above Forests.” Environmental Science & Technology 43 (18): 6976–6982.
APA
Claeys, Magda, Iinuma, Y., Szmigielski, R., Surratt, J. D., Blockhuys, F., Van Alsenoy, C., Boge, O., et al. (2009). Terpenylic acid and related compounds from the oxidation of α-pinene: implications for new particle formation and growth above forests. ENVIRONMENTAL SCIENCE & TECHNOLOGY, 43(18), 6976–6982.
Vancouver
1.
Claeys M, Iinuma Y, Szmigielski R, Surratt JD, Blockhuys F, Van Alsenoy C, et al. Terpenylic acid and related compounds from the oxidation of α-pinene: implications for new particle formation and growth above forests. ENVIRONMENTAL SCIENCE & TECHNOLOGY. 2009;43(18):6976–82.
MLA
Claeys, Magda, Yoshiteru Iinuma, Rafal Szmigielski, et al. “Terpenylic Acid and Related Compounds from the Oxidation of Α-pinene: Implications for New Particle Formation and Growth Above Forests.” ENVIRONMENTAL SCIENCE & TECHNOLOGY 43.18 (2009): 6976–6982. Print.
@article{948328,
  abstract     = {Novel secondary organic aerosol (SOA) products from the monoterpene a-pinene with unique dimer-forming properties have been identified as lactone-containing terpenoic acids, i.e., terpenylic and 2-hydroxyterpenylic acid, and diaterpenylic acid acetate. The structural characterizations were based on the synthesis of reference compounds and detailed interpretation of mass spectral data. Terpenylic acid and diaterpenylic acid acetate are early oxidation products generated upon both photooxidation and ozonolysis, while 2-hydroxyterpenylic acid is an abundant SOA tracer in ambient fine aerosol that can be explained by further oxidation of terpenylic acid. Quantum chemical calculations support that noncovalent dimer formation involving double hydrogen bonding interactions between carboxyl groups of the monomers is energetically favorable. The molecular properties allow us to explain initial particle formation in laboratory chamber experiments and are suggested to play a role in new particle formation and growth above forests, a natural phenomenon that has fascinated scientists for more than a century.},
  author       = {Claeys, Magda and Iinuma, Yoshiteru and Szmigielski, Rafal and Surratt, Jason D and Blockhuys, Frank and Van Alsenoy, Christian and Boge, Olaf and Sierau, Berko and Gomez-Gonzalez, Yadian and Vermeylen, Reinhilde and Van der Veken, Pieter and Shahgholi, Mona and Chan, Arthur WH and Herrmann, Hartmut and Seinfeld, John H and Maenhaut, Willy},
  issn         = {0013-936X},
  journal      = {ENVIRONMENTAL SCIENCE \& TECHNOLOGY},
  keyword      = {NUCLEATION,ALPHA-PINENE/O-3 REACTION,EMISSIONS,CHEMISTRY,OZONOLYSIS,AB-INITIO,MASS-SPECTROMETRY,ATMOSPHERIC PARTICLES,SECONDARY ORGANIC AEROSOL,PRODUCTS},
  language     = {eng},
  number       = {18},
  pages        = {6976--6982},
  title        = {Terpenylic acid and related compounds from the oxidation of \ensuremath{\alpha}-pinene: implications for new particle formation and growth above forests},
  url          = {http://dx.doi.org/10.1021/es9007596},
  volume       = {43},
  year         = {2009},
}

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