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On the origin of decomposition of triphenyl phosphite ozonide accelerated by ammonia or pyridine water solution
Liu, Jianbiao1; Chen, Dezhan1; Zhang, Guiqiu1; Zhang, Yuhua1; Zhang, Honghong1; Mi, Shizhen1; Shen, Guanlin2
KeywordHydroxide Accelerated Nucleophilic Addition Triphenyl Phosphite Ozonide Solvent Effect Highest Occupied Molecular Orbital (Homo)
Source PublicationJOURNAL OF MOLECULAR STRUCTURE-THEOCHEM
2010-05-30
DOI10.1016/j.theochem.2010.02.022
Volume948Issue:1-3Pages:71-77
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Physical
WOS Research AreaChemistry
WOS KeywordSINGLET OXYGEN ; NUCLEOPHILIC SUBSTITUTIONS ; GAS-PHASE ; DENSITY ; PHOSPHORUS ; MECHANISM ; OLEFINS
AbstractThe decomposition of triphenyl phosphite ozonide (TPPO) has been well recognized as a potential source of singlet oxygen (O(2), (1)Delta(g)) for the chemical oxygen-iodine laser. Experimental observations suggested that ammonia or pyridine water solution can accelerate the decomposition of TPPO, and hydroxyl ion is responsible for accelerating singlet oxygen liberation during this decomposition. In this paper, we studied the mechanism of OH(-)-accelerated reaction using density functional theory (DFT) at B3LYP/6-31+G(*) levels of theory. The calculations reveal a favorable free energy pathway for hydroxide-accelerated decomposition of TPPO, i.e. nucleophilic addition at phosphorus, followed by elimination of phenoxy group and subsequent liberation of singlet oxygen. The solvent effects were studied using a polarizable continuum model. The frontier molecular orbitals of the ozonides, atom-atom Wiberg bond index and corresponding atomic charges were also investigated to shed further light on the reaction pathway. (c) 2010 Elsevier B.V. All rights reserved.
Language英语
WOS IDWOS:000277870600013
Citation statistics
Cited Times:2[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/141750
Collection中国科学院大连化学物理研究所
Affiliation1.Shandong Normal Univ, Coll Chem Chem Engn & Mat Sci, Jinan 250014, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
Recommended Citation
GB/T 7714
Liu, Jianbiao,Chen, Dezhan,Zhang, Guiqiu,et al. On the origin of decomposition of triphenyl phosphite ozonide accelerated by ammonia or pyridine water solution[J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM,2010,948(1-3):71-77.
APA Liu, Jianbiao.,Chen, Dezhan.,Zhang, Guiqiu.,Zhang, Yuhua.,Zhang, Honghong.,...&Shen, Guanlin.(2010).On the origin of decomposition of triphenyl phosphite ozonide accelerated by ammonia or pyridine water solution.JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM,948(1-3),71-77.
MLA Liu, Jianbiao,et al."On the origin of decomposition of triphenyl phosphite ozonide accelerated by ammonia or pyridine water solution".JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM 948.1-3(2010):71-77.
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