Reactivity of Monoterpene Criegee Intermediates at
Gas–Liquid Interfaces
Version 2 2018-09-21, 02:43
Version 1 2018-09-19, 17:26
Posted on 2018-09-21 - 02:43
Biogenic monoterpenes are major sources
of Criegee intermediates
(CIs) in the troposphere. Recent studies underscored the importance
of their heterogeneous chemistry. The study of monoterpene CI reactions
on liquid surfaces, however, is challenging due to the lack of suitable
probes. Here, we report the first mass spectrometric detection of
the intermediates and products, which include labile hydroperoxides,
from reactions of CIs of representative monoterpenes (α-terpinene,
γ-terpinene, terpinolene, d-limonene, α-pinene)
with water, cis-pinonic acid (CPA) and octanoic acid
(OA) on the surface of liquid microjets. Significantly, the relative
yields of α-hydroxy-hydroperoxides production from CIs hydration
at the gas–liquid interfaceα-terpinene (1.00)
≫ d-limonene (0.18) > γ-terpinene (0.11)
∼
terpinolene (0.10) ≫ α-pinene (0.01)do not track
the rate constants of their gas-phase ozonolyses. Notably, in contrast
with the inertness of the other CIs, the CIs derived from α-terpinene
ozonolysis readily react with CPA and OA to produce C20 and C18 ester hydroperoxides, respectively. Present results
reveal hitherto unknown structural effects on the reactivities of
CIs at aqueous interfaces.
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Qiu, Junting; Ishizuka, Shinnosuke; Tonokura, Kenichi; Colussi, Agustín J.; Enami, Shinichi (2018). Reactivity of Monoterpene Criegee Intermediates at
Gas–Liquid Interfaces. ACS Publications. Collection. https://doi.org/10.1021/acs.jpca.8b06914
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AUTHORS (5)
JQ
Junting Qiu
SI
Shinnosuke Ishizuka
KT
Kenichi Tonokura
AC
Agustín J. Colussi
SE
Shinichi Enami