A cooperative hydrogen bonding system with a C-H center dot center dot center dot O hydrogen bond in ofloxacin

doi:10.1016/j.molstruc.2013.02.017

CORC > 化学研究所 > 中国科学院化学研究所

	A cooperative hydrogen bonding system with a C-H center dot center dot center dot O hydrogen bond in ofloxacin
	Gao, Xiuxiang 1; Liu, Yufeng 1,2; Li, Huizhen 1,3; Bian, Jiang 1; Zhao, Ying 2; Cao, Ye 1; Mao, Yuezhi 1; Li, Xin 1; Xu, Yizhuang 1; Ozaki, Yukihiro 4
刊名	JOURNAL OF MOLECULAR STRUCTURE
	2013-05-22
卷号	1040 页码:122-128
关键词	Nmr C-h Center Dot Center Dot Center Dot o Hydrogen Bond Ofloxacin
ISSN号	0022-2860
DOI	10.1016/j.molstruc.2013.02.017
英文摘要	We have investigated a cooperative hydrogen bonding system with a C-H center dot center dot center dot O hydrogen bond in ofloxacin by using NMR, UV-Vis spectra together with quantum chemistry calculation. Both pH-dependent NMR experiments and DFT calculation indicate that the intra-molecular C-H center dot center dot center dot O hydrogen bond between an aromatic proton and an oxygen atom from the carboxyl group is formed. Notably, the C-H center dot center dot center dot O hydrogen bond forms a cooperative hydrogen bonding system with a neighboring O-H center dot center dot center dot O hydrogen bond between the carboxyl group and the keto oxygen. The cooperative hydrogen bonding system makes the formation and disruption of the O-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds in a synergistic manner. Comparison on the pK(a) value of the carboxylic group in different fluoroquinolones compounds indicates that the C-H center dot center dot center dot O hydrogen bond plays a significant role in stabilizing the O-H center dot center dot center dot O hydrogen bond. In addition, the formation and disruption of the cooperative hydrogen bonding system could regulate the conformation of the carboxyl group, which affects the size of the conjugated system and spectral behavior of pi-pi transition of ofloxacin. 2013 Elsevier B.V. All rights reserved.
语种	英语
出版者	ELSEVIER SCIENCE BV
WOS记录号	WOS:000318961000017
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/53895]
专题	中国科学院化学研究所
通讯作者	Xu, Yizhuang
作者单位	1.Peking Univ, Coll Chem & Mol Engn, State Key Lab Rare Earth Mat Chem & Applicat, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China 2.Chinese Acad Sci, Inst Chem, Key Lab Engn Plast, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China 3.Henan Normal Univ, Coll Chem & Environm Sci, Xinxiang 453007, Peoples R China 4.Kwansei Gakuin Univ, Sch Sci & Technol, Dept Chem, Sanda 6691337, Japan
推荐引用方式 GB/T 7714	Gao, Xiuxiang,Liu, Yufeng,Li, Huizhen,et al. A cooperative hydrogen bonding system with a C-H center dot center dot center dot O hydrogen bond in ofloxacin[J]. JOURNAL OF MOLECULAR STRUCTURE,2013,1040:122-128.
APA	Gao, Xiuxiang.,Liu, Yufeng.,Li, Huizhen.,Bian, Jiang.,Zhao, Ying.,...&Wu, Jinguang.(2013).A cooperative hydrogen bonding system with a C-H center dot center dot center dot O hydrogen bond in ofloxacin.JOURNAL OF MOLECULAR STRUCTURE,1040,122-128.
MLA	Gao, Xiuxiang,et al."A cooperative hydrogen bonding system with a C-H center dot center dot center dot O hydrogen bond in ofloxacin".JOURNAL OF MOLECULAR STRUCTURE 1040(2013):122-128.