Creatinine and creatininium cation in DMSO-d6 solution. Structure and restricted internal rotation of NH2 group

Magnetic Resonance in Chemistry : MRC
Dmytro KotsyubynskyyAdam Gryff-Keller

Abstract

Investigation of 15N NMR spectra of isotopically enriched creatinine has unequivocally shown that in DMSO-d6 solution it exists as amino tautomer (2-amino-1-methylimidazoline-4-one), which in the presence of acid is protonated at N-3. Free energies of activation of the amino group rotation in creatinine and its cation have been determined to be 56 kJ/mol and 60 kJ/mol, respectively, at 298 K, by performing the simultaneous analysis of the lineshapes of -NH2 proton signals in the whole set of 1H NMR spectra recorded at various temperatures and magnetic fields. These results have been theoretically reproduced by the calculations of molecular structures and energies of creatinine and creatininium cation in their ground states and transition states of the amino group rotation, using DFT (B3LYP) method, involving the influence of the solvent.

References

Oct 20, 1971·Journal of the American Chemical Society·G L RowleyG L Kenyon
Dec 28, 1968·Nature·D H Rasmussen, A P MacKenzie
Aug 4, 1995·Science·T W BellA Kumar
Jun 29, 1999·Journal of Inherited Metabolic Disease·F J BamforthD S Wishart
Jun 19, 2002·Seminars in Neonatology : SN·J M Saudubray
Nov 8, 2002·Trends in Molecular Medicine·Avihu Boneh

❮ 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.