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@ARTICLE{Alarcn:276126,
author = {Alarcón, P. and Bohn, B. and Zetzsch, C.},
title = {{K}inetic and mechanistic study of the reaction of {OH}
radicals with methylated benzenes: 1,4-dimethyl-,
1,3,5-trimethyl-, 1,2,4,5-, 1,2,3,5- and
1,2,3,4-tetramethyl-, pentamethyl-, and hexamethylbenzene},
journal = {Physical chemistry, chemical physics},
volume = {17},
number = {19},
issn = {1463-9084},
address = {Cambridge},
publisher = {RSC Publ.},
reportid = {FZJ-2015-06603},
pages = {13053 - 13065},
year = {2015},
abstract = {The reaction of OH radicals with a series of methylated
benzenes was studied in a temperature range 300–350 K
using a flash-photolysis resonance fluorescence technique.
Reversible OH additions led to complex OH decays dependent
on the number of distinguishable adducts. Except for
hexamethylbenzene, triexponential OH decay curves were
obtained, consistent with formation of at least two adduct
species. For three compounds that can strictly form two
adduct isomers for symmetry reasons (1,4-dimethyl-,
1,3,5-trimethyl-, and 1,2,4,5-tetramethylbenzene) with OH
bound ortho or ipso with respect to the methyl groups, OH
decay curves were analysed in terms of a reaction mechanism
in which the two adducts can be formed directly by OH
addition or indirectly by isomerization. In all cases one
adduct (add1) is dominating the decomposition back to OH.
The other (add2) is more elusive and only detectable at
elevated temperatures, similar to the single OH adduct of
hexamethylbenzene. Two limiting cases of the general
reaction mechanism could be examined quantitatively:
reversible formation of add2 exclusively in the OH reaction
or by isomerization of add1. Total OH rate constants, adduct
loss rate constants and products of forward and reverse rate
constants of reversible reactions were determined. From
these quantities, adduct yields, equilibrium constants, as
well as reaction enthalpies and entropies were derived for
the three aromatics. Adduct yields strongly depend on the
selected reaction model but generally formation of add1
predominates. For both models equilibrium constants of OH
reactions lie between those of OH + benzene from the
literature and those obtained for OH + hexamethylbenzene.
The corresponding reaction enthalpies of add1 and add2
formations are in a range −87 ± 20 kJ mol−1, less
exothermic than for hexamethylbenzene (−101 kJ mol−1).
Reaction enthalpies of possible add1 → add2 isomerizations
are comparatively small. Because results for
1,3,5-trimethylbenzene are partly inconsistent with a direct
formation of add2, we promote the existence of isomerization
reactions. Moreover, based on available theoretical work in
the literature, add1 and add2 are tentatively identified as
ortho and ipso adducts, respectively. Total OH rate
constants were obtained for all title compounds. They can be
described by Arrhenius equations: kOH = A × exp(−B/T).
The parameters ln(A/(cm3 s−1)) = −25.6 ± 0.3, −25.3
± 0.6, −27.3 ± 0.3, −24.6 ± 0.3, −26.2 ± 0.4,
−26.2 ± 0.4 and −24.5 ± 0.2, and B/K = −160 ± 90,
−550 ± 180, −1120 ± 90, −330 ± 100, −820 ± 100,
−980 ± 130, and −570 ± 40 were determined for
1,4-dimethyl-, 1,3,5-trimethyl-, 1,2,4,5-, 1,2,3,5- and
1,2,3,4-tetramethyl-, pentamethyl-, and hexamethylbenzene.},
cin = {IEK-8},
ddc = {540},
cid = {I:(DE-Juel1)IEK-8-20101013},
pnm = {243 - Tropospheric trace substances and their
transformation processes (POF3-243)},
pid = {G:(DE-HGF)POF3-243},
typ = {PUB:(DE-HGF)16},
UT = {WOS:000354195300070},
pubmed = {pmid:25913267},
doi = {10.1039/C5CP00253B},
url = {https://juser.fz-juelich.de/record/276126},
}