Hydride Dissociation Energies of Six-Membered Heterocyclic Organic Hydrides Predicted by ONIOM-G4Method.
Summary of "Hydride Dissociation Energies of Six-Membered Heterocyclic Organic Hydrides Predicted by ONIOM-G4Method."
Hydride dissociation energy is of great importance in understanding the hydride-donating abilities of organic hydrides. Although the hydride dissociation energies of some organic hydrides have been experimentally measured, much less attention has been focused on the investigation of these quantities from the first principles of physics. Herein, we developed an ONIOM-G4 method and carefully benchmarked this new method against 48 experimental hydride dissociation energies of diverse bulky molecules. It was found that with the combined methods of the HF/6-31+G(d,p)//IEFPCM/Bondi1.15 solvation model, the ONIOM-G4 method can predict the hydride dissociation energies with an error bar of only 1.7 kcal/mol. With the newly developed ONIOM-G4 method, we then systematically studied the hydride dissociation energies of six categories of biologically and pharmaceutically important six-membered heterocyclic organic hydrides, namely, the organic hydrides containing 1,4-dihydropyridine, 1,4-dihydropyrazine, 1,4-oxazine, 1,4-thiazine, 4H-pyran, and 4H-thiopyran ring structures. An extensive hydride dissociation energy scale containing over 100 six-memebered heterocyclic organic hydrides has been established, which may find applications in both synthetic organic chemistry and mechanistic studies of various chemical or biological processes involving transferring of the hydride anion.
Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
This article was published in the following journal.
Name: Journal of chemical information and modeling
Medical and Biotech [MESH] Definitions
Seven membered heterocyclic rings containing a NITROGEN atom.
Compounds based on a seven-membered ring fused to a five-membered ring. Heat can rearrange them to NAPHTHALENES which have two fused six-membered rings. They are similar to guaiazulenes which are SESQUITERPENES with a six-membered ring fused to a five-membered ring.
Compounds with a five-membered heterocyclic ring with two nitrogens and a keto OXYGEN. Some are inhibitors of TNF-ALPHA production.
Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.
Compounds based on an 8-membered heterocyclic ring including an oxygen. They can be considered medium ring ethers.
The molecular and electronic structures, stabilities, bonding features, and magnetoresponsive properties of three-membered [c-Ln(3)](+/0/-) (Ln = La, Ce, Pr, Nd, Gd, Lu) and heterocyclic six-membered...
Within the general area of early main group metal chemistry, the controlled synthesis of well-defined metal hydride complexes is a rapidly developing research field. As group 1 and 2 metal complexes a...
Hydrogen pressure of 0.5-140 bar has been applied to synthesize hydrides of UCoGe. Besides an α hydride crystallizing in the structure type of the parent compound, which loses the weak ferromagneti...
Although the boron hydrides are well-known in the literature, the aluminum hydride chemistry is limited to very few systems such as AlH(3), its dimer, and its polymeric form. In view of the recent exp...
The synthesis and isolation of low coordinate methylenebis-(N-DIPP-imidazole-2-ylidene)iron((II))hydrides, (((DIPP)C)(2)CH(2))FeH(2-y)I(y) ((DIPP = 2,6-di-isopropylphenyl, y = 1 or 0), was complicated...
Organic nitrates increase levels of circulating endothelial progenitor cells (Thum et al., Arterioscler Thromb Vasc Biol. 2007 Apr;27(4):748-54). Here, we want to test the effects of two d...
This study intends to analyze the clinical characteristics of teenagers admitted to pediatric wards due to organic illness and non organic diagnosis, including patients suffering from chro...
Participants will be diagnosed with localized prostate or breast cancer and be scheduled to undergo external beam radiation therapy. Participants will either receive a placebo or organic...
The primary objective of the study is to obtain preliminary safety and tolerability data with davunetide (NAP, AL-108) in patients with a tauopathy (frontotemporal lobar degeneration [FTLD...
Trace elements, bioactive secondary metabolites and vitamins are among the most important quality parameters in plants. Yet, very little information is available on their content, bioavail...