Substituent effect on the oxidation peak potentials of phenol derivatives at ordered mesoporous carbons modified electrode and its application in determination of acidity coefficients (pKa)

CORC > 青岛生物能源与过程研究所 > 中国科学院青岛生物能源与过程研究所 > 生物传感技术团队

	Substituent effect on the oxidation peak potentials of phenol derivatives at ordered mesoporous carbons modified electrode and its application in determination of acidity coefficients (pKa)
	Zhang, Tingting 1,2,3; Lang, Qiaolin 1,2; Zeng, Lingxing 4; Li, Tie 3; Wei, Mingdeng 4; Liu, Aihua 1,2
刊名	ELECTROCHIMICA ACTA
	2014
卷号	115 页码:283-289
关键词	Ordered mesoporous carbons Substituent effect Substituted phenols Oxidation peak potential Acidity coefficient (pKa)
英文摘要	In this paper, the relationship between the electrochemical characteristics and the structure of a series of substituted phenol derivatives with electron-donating or electron-withdrawing groups were studied by voltammetry using ordered mesoporous carbons (OMCs) modified glassy carbon electrode (GCE) (OMCs/GCE). p-Nitrophenol (p-NP) and p-methylphenol were selected as models of electron-withdrawing and electron-donating groups, respectively, to illustrate the electrochemical behavior and reaction mechanism of substituted phenols. Voltammetric study showed that the oxidation peak potential (E-pa) of substituted phenols with an electron-withdrawing group was systematically higher than that of substituted phenols with an electron-donating group. That is, the direct electrochemical oxidation of substituted phenol with an electron-withdrawing group is more difficult than that of substituted phenol with an-electron-donating group. The E-pa value shifted negatively with the increase of pica for both p-substituted phenols and o-substituted phenols with the equations of pKa = -6.986 E-pa + 13.261 (for p-substituted phenols) and pKa = -7.929 E-pa + 13.831 (for o-substituted phenols). Thus, a simple and novel method was proposed for the precise prediction of the pKa of substituted phenols by determining E-pa values with voltammetry at OMCs/GCE, which matched fairly with the results calculated from Hammett's constants. Thus, the present work may provide additional strategy to determine pKa values and investigate possible mechanisms of some organic reactions. In addition, by making use of the substituent effect, different p-substituted phenols (or o-substituted phenols) can be well separated and identified at OMCs/GCE by voltametry, which may find possible applications in simultaneous detection of p-substituted phenols (or o-substituted phenols). (C) 2013 Elsevier Ltd. All rights reserved.
WOS标题词	Science & Technology ; Physical Sciences
类目[WOS]	Electrochemistry
研究领域[WOS]	Electrochemistry
关键词[WOS]	PHYSICAL-PROPERTIES ; CONSTANTS ; DISSOCIATION ; PK(A) ; PARAMETERS
收录类别	SCI
语种	英语
WOS记录号	WOS:000331424300037
公开日期	2015-12-24
内容类型	期刊论文
源URL	[http://ir.qibebt.ac.cn/handle/337004/6253]
专题	青岛生物能源与过程研究所_生物传感技术团队
作者单位	1.Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, Lab Biosensing, Qingdao 266101, Peoples R China 2.Chinese Acad Sci, Key Lab Bioenergy, Qingdao 266101, Peoples R China 3.Ocean Univ China, Coll Chem & Chem Engn, Qingdao 266100, Peoples R China 4.Fuzhou Univ, Inst Adv Energy Mat, Fuzhou 350002, Fujian, Peoples R China
推荐引用方式 GB/T 7714	Zhang, Tingting,Lang, Qiaolin,Zeng, Lingxing,et al. Substituent effect on the oxidation peak potentials of phenol derivatives at ordered mesoporous carbons modified electrode and its application in determination of acidity coefficients (pKa)[J]. ELECTROCHIMICA ACTA,2014,115:283-289.
APA	Zhang, Tingting,Lang, Qiaolin,Zeng, Lingxing,Li, Tie,Wei, Mingdeng,&Liu, Aihua.(2014).Substituent effect on the oxidation peak potentials of phenol derivatives at ordered mesoporous carbons modified electrode and its application in determination of acidity coefficients (pKa).ELECTROCHIMICA ACTA,115,283-289.
MLA	Zhang, Tingting,et al."Substituent effect on the oxidation peak potentials of phenol derivatives at ordered mesoporous carbons modified electrode and its application in determination of acidity coefficients (pKa)".ELECTROCHIMICA ACTA 115(2014):283-289.