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)

doi:10.1016/j.electacta.2013.10.158

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	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, Qiaolin1,2 ; Zeng, Lingxing 4; Li, Tie 3; Wei, Mingdeng 4; Liu, Aihua 1,2
	2014
发表期刊	ELECTROCHIMICA ACTA
卷号	115 页码:283-289
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.
文章类型	Article
关键词	Ordered Mesoporous Carbons Substituent Effect Substituted Phenols Oxidation Peak Potential Acidity Coefficient (Pka)
WOS标题词	Science & Technology ; Physical Sciences
DOI	10.1016/j.electacta.2013.10.158
关键词[WOS]	PHYSICAL-PROPERTIES ; CONSTANTS ; DISSOCIATION ; PK(A) ; PARAMETERS
收录类别	SCI
语种	英语
WOS研究方向	Electrochemistry
WOS类目	Electrochemistry
WOS记录号	WOS:000331424300037
引用统计
文献类型	期刊论文
条目标识符	http://ir.qibebt.ac.cn/handle/337004/6253
专题	生物传感技术团队（过去）
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.