The effect of formation of second hydrogen bond in adjacent two-ring resonance-assisted hydrogen bonds – Ab initio and QTAIM studies

Fazli, Mostafa; Raissi, Heidar; Chahkandi, Behzad; Aarabi, Mohammad Hossein

doi:10.1016/j.theochem.2009.12.009

Cited by 15 publications

(22 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthetic parameter Q introduced by Gilli and co-workers [129,130,137] for the description of the RAHB intramolecular H bonds in the enols of β-diketone (π-delocalization of the O=C−C=C−OH enolone fragment) can be calculated with considerable accuracy by considering the C−O, C−C, C=C, and C=O crystallographic distances in the HB rings [138,139]. However, correlations between the Q parameter and the H bond energy [140] are not always present; the same is true for the various modified Lippincott−Schroeder models [126,133].…”

Section: American Journal Of Modeling and Optimizationmentioning

confidence: 99%

It Is Important to Compute Intramolecular Hydrogen Bonding in Drug Design?

Yunta¹

2017

AJMO

View full text Add to dashboard Cite

The effect of weak intermolecular interactions on the binding affinity between ligand-protein complexes plays an important role in stabilizing a ligand at the interface of a protein structure. In this review article, we will explore the different ways of taking into account these interactions, mainly intramolecular hydrogen bonds, in docking calculations. Their possible limitations and their suitable application domains are highlighted. Inspection of the outliers of this study probed very stimulating, as it provides opportunities and inspiration to medicinal chemists, being a reminder of the impact that minimal chemical modifications can have on biological activities.

show abstract

Section: American Journal Of Modeling and Optimizationmentioning

confidence: 99%

It Is Important to Compute Intramolecular Hydrogen Bonding in Drug Design?

Yunta¹

2017

AJMO

View full text Add to dashboard Cite

show abstract

“…124 Fazli et al 128 NMR spectroscopy of the magnetically active nuclei has long been very important tool for molecular structure determination of chemical compounds. [131][132][133] Of various nuclei the most popular, particularly in organic chemistry, is 1 HNMR spectroscopy, where the resonating nuclei belong to hydrogen atoms attached in various sites in a molecule.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Quasi-aromaticity—what does it mean?

et al. 2015

View full text Add to dashboard Cite

“…The energy gaps between the CC and OO conformations are more intriguing, which for DBD, DDP and DMP are about 87.59, 111.95 and 134.37 kJ/mol, respectively. Although some authors [21,22] have been assigned these energy gaps to the IMHB energies, we believe that the total electronic energies, relative energies and energy gaps cannot be interpreted without evaluating the IMHB strength and prominence of p-ED that comprehensively discussed and analyzed in the next sections. …”

Section: Electronic Energymentioning

confidence: 99%

“…Wojtulewski and Grabowski [21] were studied the electronic structure of DBD and its derivatives, where two chelated MA rings are connected through the C=C, and concluded that the coupling of two RAHB rings does not increase the IMHB strength and resonance effect. While DDP, where two rings are joined through the C=O, was investigated by Fazli et al [22], their results show that the co-existence of two RAHB rings increases the p-ED and decreases the IMHB strength. DMP, where two chelated rings are associated through the C=C, is the latest form of two-ring RAHB systems, which has not been studied yet.…”

Section: Introductionmentioning

confidence: 99%

A comparative study of two-ring resonance-assisted hydrogen bond systems

et al. 2015

View full text Add to dashboard Cite

Two-ring resonance-assisted hydrogen bond (RAHB) systems can be obtained by merging two cis enol ring of malondialdehyde with different orientations. In the present work, a comparative theoretical study of all of the possible two-ring RAHB systems, 2,3-dihydroxy-2-butene-4-dial (DBD), 1,5-dihydroxy-1,4-diene-3-pentanone (DDP) and 2-dihydroxy-methylene-propanediol (DMP), was carried out. Also, the influence of the co-existence of two RAHB rings on the molecular structures, intramolecular hydrogen bond (IMHB) and the p-electron delocalization (p-ED) was investigated. In this regard, ab initio calculations on the various equilibrium conformations of DBD, DDP and DMP at MP2/6-311??G(d,p) level of theory have been performed and the IMHB strength of model compounds by different descriptors such as geometrical, topological, molecular orbital, spectroscopic and energetic parameters was evaluated. Then, the p-ED of DBD, DDP and DMP was estimated by using a variety of indicators, such as geometrical factor of Gilli (k), the harmonic oscillator model of aromaticity, the nucleus-independent chemical shift, the para delocalization index, the average two-center index, the aromatic fluctuation index. Finally, based on the computational results, it was found that the strength of IMHB and significance of p-ED in two-ring RAHB systems are strongly related to the relative flow of p-electrons in two rings. In other words, the parallel flows of p-electrons in DMP and DDP increase the IMHB strength and p-ED, while opposite flow of p-electrons in DBD decreases the IMHB strength and p-ED.

show abstract

The effect of formation of second hydrogen bond in adjacent two-ring resonance-assisted hydrogen bonds – Ab initio and QTAIM studies

Cited by 15 publications

References 29 publications

It Is Important to Compute Intramolecular Hydrogen Bonding in Drug Design?

It Is Important to Compute Intramolecular Hydrogen Bonding in Drug Design?

Quasi-aromaticity—what does it mean?

A comparative study of two-ring resonance-assisted hydrogen bond systems

Contact Info

Product

Resources

About