The Origin of the Non-Additivity in Resonance-Assisted Hydrogen Bond Systems

2017 ◽  
Vol 121 (44) ◽  
pp. 8535-8541 ◽  
Author(s):  
Xuhui Lin ◽  
Huaiyu Zhang ◽  
Xiaoyu Jiang ◽  
Wei Wu ◽  
Yirong Mo
Keyword(s):  
Hydrogen Bond ◽  
Resonance Assisted Hydrogen Bond

Synthesis and Structural Characterisation of New Bifunctional o-Hydroxyacetophenones – Potential Linker Molecules for Coordinative Framework Construction

2013 ◽  
Vol 68 (3) ◽  
pp. 214-222 ◽  
Author(s):  
Jörg Hübscher ◽  
Michael Günthel ◽  
Robert Rosin ◽  
Wilhelm Seichter ◽  
Florian Mertens ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
X Ray ◽  
Structural Characterisation ◽  
Crystallographic Study ◽  
Copper Coordination ◽  
Resonance Assisted Hydrogen Bond ◽  
Intramolecular Hydrogen ◽  
Fitting In ◽  
Linker Molecules

Two new linker-type molecules 1a and 1b composed of o-hydroxyacetophenone coordinative groups attached to linear ethynylene or 1,4-phenylenediethynylene spacer units have been synthesised and structurally characterised. An X-ray crystallographic study for both compounds has shown structures with strong intramolecular hydrogen bonds fitting in the model of ‘Intramolecular Resonance Assisted Hydrogen Bond (IRHAB)’. Initial coordination experiments with Cu(II) were performed and the resulting materials characterised by PXRD. The similarity of the copper coordination between these compounds and copper(II) acetylacetonate complexes was demonstrated by XPS measurements. Based on the evidence of these studies, and on elemental analysis, the formation of the corresponding coordination polymers comprising Cu(II) and the linkers has been proposed

Bonding in Tropolone, 2-Aminotropone, and Aminotroponimine: No Evidence of Resonance-Assisted Hydrogen-Bond Effects

2008 ◽  
Vol 14 (14) ◽  
pp. 4225-4232 ◽  
Author(s):  
Pablo Sanz ◽  
Otilia Mó ◽  
Manuel Yáñez ◽  
José Elguero
Keyword(s):  
Hydrogen Bond ◽  
Resonance Assisted Hydrogen Bond

Modulation of Dye Fluorescence by Photoinduced Intramolecular Charge Transfer with Resonance-Assisted Hydrogen Bond

2011 ◽  
pp. 119-154 ◽  
Author(s):  
Marcelo H. Gehlen ◽  
Emanuelle R. Simas ◽  
Robson V. Pereira ◽  
Carolina A. Sabatini
Keyword(s):  
Hydrogen Bond ◽  
Charge Transfer ◽  
Intramolecular Charge Transfer ◽  
Resonance Assisted Hydrogen Bond ◽  
Dye Fluorescence

Stereospecific Synthesis ofC2Symmetric Diamines from the Mother Diamine by Resonance-Assisted Hydrogen-Bond Directed Diaza-Cope Rearrangement

2008 ◽  
Vol 130 (36) ◽  
pp. 12184-12191 ◽  
Author(s):  
Hyunwoo Kim ◽  
Yen Nguyen ◽  
Cindy Pai-Hui Yen ◽  
Leonid Chagal ◽  
Alan J. Lough ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Stereospecific Synthesis ◽  
Cope Rearrangement ◽  
Resonance Assisted Hydrogen Bond

Symmetry breaking in the axial symmetrical configurations of enolic propanedial, propanedithial, and propanediselenal: pseudo Jahn–Teller effect versus the resonance-assisted hydrogen bond theory

2015 ◽  
Vol 93 (6) ◽  
pp. 673-684 ◽  
Author(s):  
Elahe Jalali ◽  
Davood Nori-Shargh
Keyword(s):  
Density Functional Theory ◽  
Hydrogen Bond ◽  
Symmetry Breaking ◽  
Density Functional ◽  
Teller Effect ◽  
Electron Delocalization ◽  
Functional Theory ◽  
Jahn Teller ◽  
Jahn Teller Effect ◽  
Resonance Assisted Hydrogen Bond

The origin of the symmetry breaking in the axial symmetrical configurations of enolic propanedial (1), propanedithial (2), and propanediselenal (3) have been investigated by means of time-dependence density functional theory and natural bond orbital interpretations. The results obtained at the quantum chemistry composite (G2MP2, CBS-QB3), ab initio molecular orbital (MP2/6-311++G**), and hybrid density functional theory (B3LYP/6-311++G**) levels of theory showed that the hydrogen-centered synchronous axial symmetrical (C2v) configurations of compounds 1–3 possessing the maximum π-electron delocalization within the M1=C2–C3=C4–M5–H6 keto-enol groups are less stable than their corresponding plane symmetrical (Cs) forms. Importantly, the symmetry breaking in the C2v configurations of the enol forms of compounds 1–3 to their corresponding plane symmetrical Cs configurations is due to the pseudo Jahn–Teller effect (PJTE) by mixing the ground A1 and excited B2 electronic states resulting in a PJT (A1 + B2) ⊗ b2 problem. We may expect that by the decrease of the energy gaps between reference states in the C2v forms that are involved in the PJTE decrease from compound 1 to compound 3, the PJT stabilization energy (PJTSE) may increase but the results obtained showed that the corresponding PJTSEs decrease. This fact can be justified by the increase of the electron delocalizations from the nonbonding orbitals of the C=M moieties to the antibonding orbitals of the H–M bonds, which leads to an increase of the π-electron delocalization within the M1=C2–C3=C4–M5–H6 keto-enol groups. In confrontation between the impacts of the resonance-assisted hydrogen bond and PJTE in the structural and configurational properties of compounds 1–3, PJTE has an overwhelming contribution and causes the symmetry breaking of the C2v configurations to their corresponding Cs forms. The correlations between the structural parameters, synchronicity indices, natural charges, PJTSEs, electron delocalizations, and the hardness of compounds 1–3 have been investigated.

Polarized IR spectra of resonance assisted hydrogen bond (RAHB) in 2-hydroxyazobenzenes

2006 ◽  
Vol 326 (2-3) ◽  
pp. 458-464 ◽  
Author(s):  
Maria Rospenk ◽  
Paulina Majewska ◽  
Boguslawa Czarnik-Matusewicz ◽  
Lucjan Sobczyk
Keyword(s):  
Hydrogen Bond ◽  
Ir Spectra ◽  
Resonance Assisted Hydrogen Bond

A facile colorimetric and fluorescent cyanide chemosensor: utilization of the nucleophilic addition induced by resonance-assisted hydrogen bond

Tetrahedron ◽  
2015 ◽  
Vol 71 (5) ◽  
pp. 857-862 ◽  
Author(s):  
Qiao Li ◽  
Jian-hui Zhang ◽  
Yi Cai ◽  
Wen-juan Qu ◽  
Guo-ying Gao ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Nucleophilic Addition ◽  
Resonance Assisted Hydrogen Bond
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