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Crystal Structure and Tautomerism Study of the Mono-protonated Metformin Salt
Wei, Xiaodan1; Fan, Yuhua1; Bi, Caifeng1; Yan, Xingchen1,2; Zhang, Xia1; Li, Xin1
2014-12-20
Source PublicationBULLETIN OF THE KOREAN CHEMICAL SOCIETY
Volume35Issue:12Pages:3495-3501
Abstract

A novel crystal, the mono-protonated metformin acetate (1), was obtained and characterized by elemental analysis, IR spectroscopy and X-ray crystallography. It was found that one of the imino group in the metformin cation was protonated along with the proton transfer from the secondary amino group to the other imino group. Its crystal structure was then compared with the previously reported diprotonated metformin oxalate (2). The difference between them is that the mono-protonated metformin cations can be linked by hydrogen bonding to form dimers while the diprotonated metformin cations cannot. Both of them are stabilized by intermolecular hydrogen bonds to assemble a 3-D supermolecular structure. The four potential tautomer of the mono-protonated metformin cation (tautomers 1a, 1b, 1c and 1d) were optimized and their single point energies were calculated by Density Functional Theory (DFT) B3LYP method based on the Polarized Continuum Model (PCM) in water, which shows that the most likely existed tautomer in human cells is the same in the crystal structure. Based on the optimized structure, their Wiberg bond orders, Natural Population Analysis (NPA) atomic charges, molecular electrostatic potential (MEP) maps were calculated to analyze their electronic structures, which were then compared with the corresponding values of the diprotonated metformin cation (cation 2) and the neutral metformin (compound 3). Finally, the possible tautomeric mechanism of the monoprotonated metformin cation was discussed based on the observed phenomena.

SubtypeArticle
KeywordMetformin Crystal Structure Theoretical Calculation Tautomerism
WOS HeadingsScience & Technology ; Physical Sciences
DOI10.5012/bkcs.2014.35.12.3495
WOS KeywordGASTRIC-ACID-SECRETION ; SUPRAMOLECULAR CHEMISTRY ; BIGUANIDE DERIVATIVES ; COMPLEXES ; DNA ; RECOGNITION ; RATS
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000346113000016
Citation statistics
Cited Times:6[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.qibebt.ac.cn/handle/337004/6307
Collection仿生能源与储能系统团队
Affiliation1.Ocean Univ China, Coll Chem & Chem Engn, Key Lab Marine Chem Theory & Technol, Minist Educ, Qingdao 266100, Shandong, Peoples R China
2.Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, Qingdao 266101, Peoples R China
Recommended Citation
GB/T 7714
Wei, Xiaodan,Fan, Yuhua,Bi, Caifeng,et al. Crystal Structure and Tautomerism Study of the Mono-protonated Metformin Salt[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY,2014,35(12):3495-3501.
APA Wei, Xiaodan,Fan, Yuhua,Bi, Caifeng,Yan, Xingchen,Zhang, Xia,&Li, Xin.(2014).Crystal Structure and Tautomerism Study of the Mono-protonated Metformin Salt.BULLETIN OF THE KOREAN CHEMICAL SOCIETY,35(12),3495-3501.
MLA Wei, Xiaodan,et al."Crystal Structure and Tautomerism Study of the Mono-protonated Metformin Salt".BULLETIN OF THE KOREAN CHEMICAL SOCIETY 35.12(2014):3495-3501.
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