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Formation of 5- and 6-methyl-1H-indene (C10H10) via the reactions of the para-tolyl radical (C6H4CH3) with allene (H2CCCH2) and methylacetylene (HCCCH3) under single collision conditions.
Phys Chem Chem Phys. 2015 Apr 28; 17(16):10510-9.PC

Abstract

The reactions of the p-tolyl radical with allene-d4 and methylacetylene-d4 as well as of the p-tolyl-d7 radical with methylacetylene-d1 and methylacetylene-d3 were carried out under single collision conditions at collision energies of 44-48 kJ mol(-1) and combined with electronic structure and statistical (RRKM) calculations. Our experimental results indicated that the reactions of p-tolyl with allene-d4 and methylacetylene-d4 proceeded via indirect reaction dynamics with laboratory angular distributions spanning about 20° in the scattering plane. As a result, the center-of-mass translational energy distribution determined a reaction exoergicity of 149 ± 28 kJ mol(-1) and exhibited a pronounced maximum at around 20 to 30 kJ mol(-1). In addition, the center-of-mass angular flux distribution T(θ) depicted a forward-backward symmetry and indicated geometric constraints upon the decomposing complex(es). Combining with calculations, these results propose that the bicyclic polycyclic aromatic hydrocarbons, 6-methyl-1H-indene (p1) and 5-methyl-1H-indene (p2), are formed under single collision conditions at fractions of at least 85% in both reaction systems. For the p-tolyl-methylacetylene system, experiments with partially deuterated reactants also reveal the formation of a third isomer p5 (1-methyl-4-(1-propynyl)benzene) at levels of 5-10%, highlighting the importance in conducting reactions with partially deuterated reactants to elucidate the underlying reaction pathways comprehensively.

Authors+Show Affiliations

Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii, USA. ralfk@hawaii.edu.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

25806373

Citation

Yang, Tao, et al. "Formation of 5- and 6-methyl-1H-indene (C10H10) Via the Reactions of the Para-tolyl Radical (C6H4CH3) With Allene (H2CCCH2) and Methylacetylene (HCCCH3) Under Single Collision Conditions." Physical Chemistry Chemical Physics : PCCP, vol. 17, no. 16, 2015, pp. 10510-9.
Yang T, Parker DS, Dangi BB, et al. Formation of 5- and 6-methyl-1H-indene (C10H10) via the reactions of the para-tolyl radical (C6H4CH3) with allene (H2CCCH2) and methylacetylene (HCCCH3) under single collision conditions. Phys Chem Chem Phys. 2015;17(16):10510-9.
Yang, T., Parker, D. S., Dangi, B. B., Kaiser, R. I., & Mebel, A. M. (2015). Formation of 5- and 6-methyl-1H-indene (C10H10) via the reactions of the para-tolyl radical (C6H4CH3) with allene (H2CCCH2) and methylacetylene (HCCCH3) under single collision conditions. Physical Chemistry Chemical Physics : PCCP, 17(16), 10510-9. https://doi.org/10.1039/c4cp04288c
Yang T, et al. Formation of 5- and 6-methyl-1H-indene (C10H10) Via the Reactions of the Para-tolyl Radical (C6H4CH3) With Allene (H2CCCH2) and Methylacetylene (HCCCH3) Under Single Collision Conditions. Phys Chem Chem Phys. 2015 Apr 28;17(16):10510-9. PubMed PMID: 25806373.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Formation of 5- and 6-methyl-1H-indene (C10H10) via the reactions of the para-tolyl radical (C6H4CH3) with allene (H2CCCH2) and methylacetylene (HCCCH3) under single collision conditions. AU - Yang,Tao, AU - Parker,Dorian S N, AU - Dangi,Beni B, AU - Kaiser,Ralf I, AU - Mebel,Alexander M, PY - 2015/3/26/entrez PY - 2015/3/26/pubmed PY - 2015/3/26/medline SP - 10510 EP - 9 JF - Physical chemistry chemical physics : PCCP JO - Phys Chem Chem Phys VL - 17 IS - 16 N2 - The reactions of the p-tolyl radical with allene-d4 and methylacetylene-d4 as well as of the p-tolyl-d7 radical with methylacetylene-d1 and methylacetylene-d3 were carried out under single collision conditions at collision energies of 44-48 kJ mol(-1) and combined with electronic structure and statistical (RRKM) calculations. Our experimental results indicated that the reactions of p-tolyl with allene-d4 and methylacetylene-d4 proceeded via indirect reaction dynamics with laboratory angular distributions spanning about 20° in the scattering plane. As a result, the center-of-mass translational energy distribution determined a reaction exoergicity of 149 ± 28 kJ mol(-1) and exhibited a pronounced maximum at around 20 to 30 kJ mol(-1). In addition, the center-of-mass angular flux distribution T(θ) depicted a forward-backward symmetry and indicated geometric constraints upon the decomposing complex(es). Combining with calculations, these results propose that the bicyclic polycyclic aromatic hydrocarbons, 6-methyl-1H-indene (p1) and 5-methyl-1H-indene (p2), are formed under single collision conditions at fractions of at least 85% in both reaction systems. For the p-tolyl-methylacetylene system, experiments with partially deuterated reactants also reveal the formation of a third isomer p5 (1-methyl-4-(1-propynyl)benzene) at levels of 5-10%, highlighting the importance in conducting reactions with partially deuterated reactants to elucidate the underlying reaction pathways comprehensively. SN - 1463-9084 UR - https://www.unboundmedicine.com/medline/citation/25806373/Formation_of_5__and_6_methyl_1H_indene__C10H10__via_the_reactions_of_the_para_tolyl_radical__C6H4CH3__with_allene__H2CCCH2__and_methylacetylene__HCCCH3__under_single_collision_conditions_ L2 - https://doi.org/10.1039/c4cp04288c DB - PRIME DP - Unbound Medicine ER -
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