NMR crystallography of 2-acylamino-6-[1H]-pyridones: Solid-state NMR, GIPAW computational, and single crystal X-ray diffraction studies

被引：12

作者：

Osmialowski, Borys ^{[1
]}

Kolehmainen, Erkki ^{[2
]}

Ikonen, Satu ^{[2
]}

Ahonen, Kari ^{[2
]}

Lofman, Miika ^{[2
]}

机构：

[1] Univ Technol & Life Sci, Fac Chem Technol & Engn, PL-85326 Bydgoszcz, Poland

[2] Univ Jyvaskyla, Dept Chem, FI-40014 Jyvaskyla, Finland

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2011年 / 1006卷 / 1-3期

基金：

芬兰科学院;

关键词：

Hydrogen bonding; X-ray diffraction; NMR crystallography; GIPAW calculations; HYDROGEN-BONDS; SUPRAMOLECULAR POLYMERS; TAUTOMERIC EQUILIBRIA; ASSOCIATION; 2,6-BIS(ACYLAMINO)PYRIDINES; COMPLEXATION; SPECTROSCOPY; SUBSTITUENT; DERIVATIVES; CYTOSINE;

D O I：

10.1016/j.molstruc.2011.10.034

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

2-Acylamino-6-[1H]-pyridones [acyl = RCO, where R = methyl (1), ethyl (2), iso-propyl (3), tert-butyl (4), and 1-adamantyl (5)] have been synthesized and characterized by NMR spectroscopy. From three congeners, 2, 3 and 5, also single crystal X-ray structures have been solved. For these derivatives GIPAW calculations acts as a "bridge" between solid-state NMR data and calculated chemical shifts based on X-ray determined geometry. In crystals all three compounds exist as pyridone tautomers possessing similar six-membered ring structure stabilized by intramolecular C=O center dot center dot center dot HN hydrogen bond. Theoretical GIPAW calculated and experimental C-13 and N-15 CPMAS NMR shifts are in excellent agreement with each other. (C) 2011 Elsevier B.V. All rights reserved.

引用

页码：678 / 683

页数：6

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