Zwitterion formation and subsequent carboxylate-pyridinium NH synthon generation through isomerization of 2-anilinonicotinic acid

doi:10.1039/c8ce01255e

CORC > 武汉植物园 > 中国科学院武汉植物园

	Zwitterion formation and subsequent carboxylate-pyridinium NH synthon generation through isomerization of 2-anilinonicotinic acid
	Yue, Pengyun 1; Dong, Caiqiao 2; Zhang, Mingtao 2; Xu, Danrui 1; Parkin, Sean 3; Li, Tonglei 4; Li, Conggang 5; Yu, Faquan 1; Long, Sihui 1
刊名	CRYSTENGCOMM
	2018-10-28
卷号	20 期号:40 页码:6126-6132
ISSN号	1466-8033
DOI	10.1039/c8ce01255e
英文摘要	Through structural modification of 2-anilinonicotinic acid by isomerization, the pK(a) between the carboxylic acid and pyridinium NH increased dramatically over the threshold to form zwitterions in the newly designed 4-anilinonicotinic acids. This in turn led to the formation of a hydrogen bond between carboxylate and pyridinium NH, and the absence of two commonly observed synthons, i.e., the acid-acid homosynthon and acid-pyridine heterosynthon. The new synthon has a stronger hydrogen bond than the acid-acid homosynthon and the acid-pyridine heterosynthon, as suggested by theoretical calculations. This, together with the much larger pK(a), explains its formation.
资助项目	Natural Science Foundation of Hubei Province[2014CFB787] ; National Science Foundation (NSF) MRI program[CHE0319176] ; National Science Foundation (NSF) MRI program[CHE1625732]
WOS研究方向	Chemistry ; Crystallography
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000448342600003
内容类型	期刊论文
源URL	[http://202.127.146.157/handle/2RYDP1HH/3929]
专题	中国科学院武汉植物园
通讯作者	Yu, Faquan; Long, Sihui
作者单位	1.Wuhan Inst Technol, Sch Chem Engn & Pharm, Key Lab Green Chem Proc,Minist Educ, Hubei Key Lab Novel Reactor & Green Chem Technol, Wuhan, Hubei, Peoples R China 2.Nankai Univ, Dept Chem, Tianjin, Peoples R China 3.Univ Kentucky, Dept Chem, Lexington, KY 40506 USA 4.Purdue Univ, Dept Ind & Phys Pharm, W Lafayette, IN 47907 USA 5.Chinese Acad Sci, Wuhan Inst Phys & Math, Wuhan, Hubei, Peoples R China
推荐引用方式 GB/T 7714	Yue, Pengyun,Dong, Caiqiao,Zhang, Mingtao,et al. Zwitterion formation and subsequent carboxylate-pyridinium NH synthon generation through isomerization of 2-anilinonicotinic acid[J]. CRYSTENGCOMM,2018,20(40):6126-6132.
APA	Yue, Pengyun.,Dong, Caiqiao.,Zhang, Mingtao.,Xu, Danrui.,Parkin, Sean.,...&Long, Sihui.(2018).Zwitterion formation and subsequent carboxylate-pyridinium NH synthon generation through isomerization of 2-anilinonicotinic acid.CRYSTENGCOMM,20(40),6126-6132.
MLA	Yue, Pengyun,et al."Zwitterion formation and subsequent carboxylate-pyridinium NH synthon generation through isomerization of 2-anilinonicotinic acid".CRYSTENGCOMM 20.40(2018):6126-6132.