Intramolecular NH⋯O resonance-assisted hydrogen bonds in crystal structures of oxaphosphinanes and chromones—DFT calculations and AIM analysis

Małecka, Magdalena

doi:10.1016/j.molstruc.2006.07.030

Cited by 15 publications

(16 citation statements)

References 25 publications

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“…Accordingly, the presumed existence of the two species stabilized by intramolecular hydrogen bonds (amide 2 a/iminol 2 c tautomers) was included. [4][5][6] The data clearly indicates that, in the gas phase, tautomers 2 b and 2 c are thermodynamically unstable when compared to tautomer 2 a. The significance of the hydrogen bond as a stabilizing force on the structure of 2 can be explained by the relatively large enthalpies (see Table 1).…”

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confidence: 94%

Towards the Discovery of a Novel Class of Monoamine Oxidase Inhibitors: Structure–Property–Activity and Docking Studies on Chromone Amides

et al. 2011

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mentioning

confidence: 94%

Towards the Discovery of a Novel Class of Monoamine Oxidase Inhibitors: Structure–Property–Activity and Docking Studies on Chromone Amides

et al. 2011

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“…1) as a continuing study of the crystal structures of chromone derivatives [1,2] and the recent research on the electron-density (ED) distribution in this group of compounds [3,4].…”

Section: Introductionmentioning

confidence: 99%

Electron-density studies on hydrogen bonding in chromone derivatives. Part II: comparative study

2011

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The experimental electron density of a chromone derivative was determined from a multipole refinement of 100 K X-ray synchrotron data and complemented by theoretical calculations with experimental and optimized geometry. Atomic and topological properties were obtained using the Quantum Theory of Atoms in Molecules approach. The examination of topological parameters unambiguously showed p-delocalization within the H-bonded ring. The application of source function analysis confirmed the intramolecular N-HÁÁÁO hydrogen bond to be a resonance-assisted hydrogen bond. The topological study confirmed the covalent nature of N-HÁÁÁO interaction and the electrostatic nature of weak C-HÁÁÁO interactions.

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“…The chromone and coumarin derivatives, as well as oxaphosphinane ones which also contain a RAHB system, were systematically examined experimentally and theoretically (Małecka, 2007;Małecka et al, 2004;Grabowski & Małecka, 2006;Rybarczyk-Pirek et al, 2002, 2006.…”

Section: Introductionmentioning

confidence: 99%

Electron density studies on hydrogen bonding in two chromone derivatives

Małecka

Chęcińska

Rybarczyk‐Pirek

et al. 2010

Acta Crystallogr Sect B

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The experimental electron densities of two chromone derivatives have been determined from X-ray synchrotron diffraction data at low temperature (100 K). Topological analysis of the electron density has been used to analyze the formation of resonance-assisted hydrogen bonds (RAHBs). Geometrical and topological parameters confirm π-electron delocalization within the hydrogen-bonded ring. In addition, weak C-H···O interactions were identified in both structures. Hydrogen-bond energies allowed medium and weak hydrogen bonds to be distinguished.

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Intramolecular NH⋯O resonance-assisted hydrogen bonds in crystal structures of oxaphosphinanes and chromones—DFT calculations and AIM analysis

Cited by 15 publications

References 25 publications

Towards the Discovery of a Novel Class of Monoamine Oxidase Inhibitors: Structure–Property–Activity and Docking Studies on Chromone Amides

Towards the Discovery of a Novel Class of Monoamine Oxidase Inhibitors: Structure–Property–Activity and Docking Studies on Chromone Amides

Electron-density studies on hydrogen bonding in chromone derivatives. Part II: comparative study

Electron density studies on hydrogen bonding in two chromone derivatives

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