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	Effect of the phosphoryl substituent in the linear nitrone on the spin trapping of superoxide radical and the stability of the superoxide adduct: combined experimental and theoretical studies
	Liu, Yang-Ping; Wang, Lan-Fen; Nie, Zhou; Ji, Yi-Qiong; Liu, Yang; Liu, Ke-Jian; Tian, Qiu
刊名	Journal of organic chemistry
	2006-09-29
卷号	71期号:20页码:7753-7762
ISSN号	0022-3263
DOI	10.1021/jo061204m
通讯作者	Liu, yang(yliu@iccas.ac.cn)
英文摘要	A new phosphorylated linear nitrone n-(4-hydroxybenzyliene)-1-diethoxyphosphoryl-1-methylethylamine n-oxide (4-hoppn) was synthesized, and its x-ray structure was determined. the spin trapping ability of various kinds of free radicals by 4-hoppn was evaluated. kinetic study of decay of the superoxide spin adduct (4-hoppn-ooh) shows the half-life time of 8.8 min. on the basis of the x-ray structural coordinates, theoretical analyses using density functional theory (dft) calculations at the b3lyp/6-31+ g(d,p)//b3lyp/6-31g(d) level were performed on spin-trapping reactions of superoxide radical with 4-hoppn and pbn and three possible decay routes for their corresponding superoxide adducts. the comparative calculations on the spin-trapping reactions with superoxide radical predicted that both spin traps share an identical reaction type and have comparable potency when spin trapping superoxide radical. analysis of the optimized geometries of 4-hoppn-ooh and pbn-ooh reveals that an introduction of the phosphoryl group can efficiently stabilize the spin adduct through the intramolecular h-bonds, the intramolecular nonbonding attractive interactions, as well as the bulky steric protection. examination of the decomposition thermodynamics of 4-hoppn-ooh and pbn-ooh further supports the stabilizing role of the phosphoryl group to a linear phosphorylated spin adduct.
WOS关键词	5-DIETHOXYPHOSPHORYL-5-METHYL-1-PYRROLINE N-OXIDE ; OXYGEN-CENTERED RADICALS ; LIPID-PEROXIDATION ; HYDROXYL RADICALS ; CRYSTAL-STRUCTURE ; CYCLIC NITRONES ; AQUEOUS-MEDIA ; ANION ADDUCT ; IN-VITRO ; DECAY
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000240677900032
内容类型	期刊论文
URI标识	http://www.corc.org.cn/handle/1471x/2378592
专题	中国科学院大学
通讯作者	Liu, Yang
作者单位	1.Chinese Acad Sci, Inst Chem, Ctr Mol Sci, State Key Lab Struct Chem Unstable & Stabel Speci, Beijing 100080, Peoples R China 2.Chinese Acad Sci, Grad Sch, Beijing 100080, Peoples R China 3.Univ New Mexico, Coll Pharm, Albuquerque, NM 87131 USA
推荐引用方式 GB/T 7714	Liu, Yang-Ping,Wang, Lan-Fen,Nie, Zhou,et al. Effect of the phosphoryl substituent in the linear nitrone on the spin trapping of superoxide radical and the stability of the superoxide adduct: combined experimental and theoretical studies[J]. Journal of organic chemistry,2006,71(20):7753-7762.
APA	Liu, Yang-Ping.,Wang, Lan-Fen.,Nie, Zhou.,Ji, Yi-Qiong.,Liu, Yang.,...&Tian, Qiu.(2006).Effect of the phosphoryl substituent in the linear nitrone on the spin trapping of superoxide radical and the stability of the superoxide adduct: combined experimental and theoretical studies.Journal of organic chemistry,71(20),7753-7762.
MLA	Liu, Yang-Ping,et al."Effect of the phosphoryl substituent in the linear nitrone on the spin trapping of superoxide radical and the stability of the superoxide adduct: combined experimental and theoretical studies".Journal of organic chemistry 71.20(2006):7753-7762.

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