Intramolecular O-H⋯O and C-H⋯O hydrogen bond cooperativity in D-glucopyranose and D-galactopyranose-A DFT/GIAO, QTAIM/IQA, and NCI approach

Magnetic Resonance in Chemistry : MRC
John S Lomas

Abstract

Density functional theory calculations are used to compute proton nuclear magnetic resonance (NMR) chemical shifts, interatomic distances, atom-atom interaction energies, and atomic charges for partial structures and conformers of α-D-glucopyranose, β-D-glucopyranose, and α-D-galactopyranose built up by introducing OH groups into 2-methyltetrahydropyran stepwisely. For the counterclockwise conformers, the most marked effects on the NMR shift and the charge on the OH1 proton are produced by OH2, those of OH3 and OH4 being somewhat smaller. This argues for a diminishing cooperative effect. The effect of OH6 depends on the configuration of the hydroxymethyl group and the position, axial or equatorial, of OH4, which controls hydrogen bonding in the 1,3-diol motif. Variations in the interaction energies reveal that a "new" hydrogen bond is sometimes formed at the expense of a preexisting one, probably due to geometrical constraints. Whereas previous work showed that complexing a conformer with pyridine affects only the nearest neighbour, successive OH groups increase the interaction energy of the N⋯H1 hydrogen bond and reduce its length. Analogous results are obtained for the clockwise conformers. The interaction energies for C-H⋯OH...Continue Reading

References

Oct 28, 1996·Physical Review Letters·J P PerdewM Ernzerhof
Jul 18, 2002·Chemical Communications : Chem Comm·Praveen K ThallapallyGautam R Desiraju
Nov 15, 2002·Journal of the American Chemical Society·Roger A Klein
Jul 18, 2003·Journal of Computational Chemistry·Jenn-Huei LiiNorman L Allinger
Jul 23, 2004·The Journal of Chemical Physics·A Martin PendasE Francisco
Aug 27, 2004·Journal of Mass Spectrometry : JMS·Jean-Yves Salpin, Jeanine Tortajada
Jun 17, 2005·Chemical Communications : Chem Comm·Gautam R Desiraju
Dec 27, 2005·The Journal of Physical Chemistry. B·Jennifer L DashnauJane M Vanderkooi
Jan 18, 2006·Carbohydrate Research·Frank A MomanyWayne B Bosma
Mar 28, 2007·Carbohydrate Research·Osamu TakahashiMotohiro Nishio
Jul 17, 2007·Progress in Biophysics and Molecular Biology·Pinak Chakrabarti, Rajasri Bhattacharyya
Aug 21, 2007·Proteins·Vikas Nanda, Ann Schmiedekamp
Aug 28, 2007·The Journal of Organic Chemistry·Alessandro BagnoGiacomo Saielli
Dec 19, 2007·The Journal of Physical Chemistry. a·Milind M DeshmukhShridhar R Gadre
Nov 8, 2008·The Journal of Physical Chemistry. B·Christopher B Barnett, Kevin J Naidoo
Sep 12, 2009·Angewandte Chemie·Christopher A Hunter, Harry L Anderson
Apr 17, 2010·Journal of the American Chemical Society·Erin R JohnsonWeitao Yang
Jul 17, 2010·Progress in Nuclear Magnetic Resonance Spectroscopy·Ioannis P Gerothanassis
Nov 22, 2012·Magnetic Resonance in Chemistry : MRC·John S Lomas
Jun 13, 2013·Journal of Molecular Modeling·Sedat Karabulut, Jerzy Leszczynski
Oct 10, 2013·Angewandte Chemie·Isabel PeñaJosé L Alonso
Aug 1, 2014·Carbohydrate Research·Josué M SillaMatheus P Freitas
Sep 27, 2014·Physical Chemistry Chemical Physics : PCCP·Isabel PeñaJosé L Alonso
Oct 25, 2014·Chemical Reviews·Shridhar R GadreNityananda Sahu
May 27, 2015·Chemical Communications : Chem Comm·Isabel PeñaJosé L Alonso
Aug 13, 2013·Journal of Chemical Theory and Computation·Joseph R LaneHenrik G Kjaergaard
Aug 14, 2012·Journal of Chemical Theory and Computation·W M C Sameera, Dimitrios A Pantazis
Jan 1, 2006·Journal of Chemical Theory and Computation·E FranciscoM A Blanco
Feb 4, 2016·Chemical Reviews·A Subha Mahadevi, G Narahari Sastry
Jun 2, 2016·Magnetic Resonance in Chemistry : MRC·John S LomasFrançois Maurel
Apr 23, 2017·Magnetic Resonance in Chemistry : MRC·John S Lomas, Laurent Joubert
Oct 19, 2017·Journal of Chemical Theory and Computation·Kevin B MooreHenry F Schaefer

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.