Hydrogen bond in 3-acetyl-4-hydroxycoumarin: X-ray diffraction study and quantum-chemical calculations
作者： K. A. Lyssenko , M. Yu. Antipin
关键词:
摘要: The proton transfer and the character of strong intramolecular O--H...O hydrogen bond (O...O 2.442 A) in 3-acetyl-4-hydroxycoumarin were analyzed based on results X-ray diffraction study temperature range from 100 to 353 K quantum-chemical B3LYP/6-31G(d,p) calculations. barrier along H-bond line is low (2 kcal mol–1). However, no was observed crystal at K. Bader's topological analysis electron density distribution both isolated molecule demonstrated that corresponds an intermediate type interatomic interactions (E(r) 0 critical point (3, –1)).
springer.com
sci-hub.se 参考文章(35)
Zvi Rappoport, The Chemistry of enols Wiley. ,(1990)
F Richard, R Bader, Atoms in molecules : a quantum theory Clarendon Press. ,(1990)
Pietro Roversi, Felicita Merati, Riccardo Destro, Mario Barzaghi, Charge density in crystalline citrinin from X-ray diffraction at 19 K Canadian Journal of Chemistry. ,vol. 74, pp. 1145- 1161 ,(1996) , 10.1139/V96-129
E Espinosa, E Molins, C Lecomte, Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities Chemical Physics Letters. ,vol. 285, pp. 170- 173 ,(1998) , 10.1016/S0009-2614(98)00036-0
Dennis Madsen, Claus Flensburg, Sine Larsen, Properties of the Experimental Crystal Charge Density of Methylammonium Hydrogen Maleate. A Salt with a Very Short Intramolecular O−H−O Hydrogen Bond Journal of Physical Chemistry A. ,vol. 102, pp. 2177- 2188 ,(1998) , 10.1021/JP972419Q
Roland Boese, Mikhail Yu Antipin, Dieter Bläser, Konstantin A Lyssenko, None, Molecular Crystal Structure of Acetylacetone at 210 and 110 K: Is the Crystal Disorder Static or Dynamic? Journal of Physical Chemistry B. ,vol. 102, pp. 8654- 8660 ,(1998) , 10.1021/JP980121+
Russell J. Boyd, Sai Cheng Choi, Hydrogen bonding between nitriles and hydrogen halides and the topological properties of molecular charge distributions Chemical Physics Letters. ,vol. 129, pp. 62- 65 ,(1986) , 10.1016/0009-2614(86)80169-5
Mark E Tuckerman, Dominik Marx, Michael L Klein, Michele Parrinello, On the quantum nature of the shared proton in hydrogen bonds Science. ,vol. 275, pp. 817- 820 ,(1997) , 10.1126/SCIENCE.275.5301.817
Mireia Garcia-Viloca, Angels González-Lafont, José M. Lluch, Theoretical Study of the Low-Barrier Hydrogen Bond in the Hydrogen Maleate Anion in the Gas Phase. Comparison with Normal Hydrogen Bonds Journal of the American Chemical Society. ,vol. 119, pp. 1081- 1086 ,(1997) , 10.1021/JA962662N
F. L. Hirshfeld, Can X‐ray data distinguish bonding effects from vibrational smearing? Acta Crystallographica Section A. ,vol. 32, pp. 239- 244 ,(1976) , 10.1107/S0567739476000533