Conformational Landscape and Polymorphism in 5-Acetic Acid Hydantoin

The Journal of Physical Chemistry. a
B A NogueiraRui Fausto

Abstract

The conformational space of 5-acetic acid hydantoin {5AAH; [2-(2,5-dioxoimidazolidin-4-yl)acetic acid]} was investigated by quantum chemical calculations performed at the DFT(B3LYP)/6-311++G(d,p) level of theory. A total of 13 conformers were located in the potential energy surface of the molecule, six of them bearing the carboxylic group in the cis arrangement (O═C-O-H dihedral equal to ∼0°) and the other seven possessing this group in the trans configuration (O═C-O-H dihedral equal to ∼180°). The most stable conformer (cis-I) was trapped from the gas phase into a low temperature argon matrix (10 K), and its infrared spectrum was fully assigned, also with help of results of normal coordinates' analysis based on the DFT computed vibrational data. The electronic structure of this conformer was analyzed by using the natural bond orbital (NBO) method. The investigation of the thermal properties of 5AAH was undertaken by differential scanning calorimetry (DSC), polarized light thermal microscopy (PLTM) and Raman spectroscopy, allowing identification of five different polymorphs. Very interestingly, in the room temperature stable polymorph the molecular units of 5AAH assume the geometry of the highest-energy conformer predicted by t...Continue Reading

References

Sep 30, 1975·Annals of the New York Academy of Sciences·I B ChatterjeeN Subramanian
Sep 28, 1992·Journal of Medicinal Chemistry·R N ComberJ A Secrist
Mar 1, 1991·The Journal of Antibiotics·M NakajimaT Haneishi
Sep 15, 1988·Physical Review A: General Physics·A D Becke
Dec 25, 2003·Journal of the American Chemical Society·Ermelinda M S MaçôasMarkku Räsänen
Oct 7, 2004·Acta Crystallographica. Section C, Crystal Structure Communications·Fang-Lei YuDavid J Watkin
Jul 15, 2006·The Journal of Physical Chemistry. a·Ermelinda M S MaçôasMarkku Räsänen
Aug 15, 2008·European Journal of Medicinal Chemistry·Sham M SondhiP P Gupta
Nov 19, 2008·Biochemical Pharmacology·C V KavithaSathees C Raghavan
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
Apr 25, 2009·The Journal of Physical Chemistry. a·Mário T S RosadoJosé S Redinha
Dec 7, 2006·Physical Chemistry Chemical Physics : PCCP·Igor D RevaJ S Redinha
Aug 6, 2010·Chemical & Pharmaceutical Bulletin·Fumiko FujisakiKunihiro Sumoto
Apr 16, 2011·Postgraduate Medical Journal·Joanna M Zakrzewska, Roddy McMillan
Feb 7, 2012·Acta Crystallographica. Section C, Crystal Structure Communications·Valeska GerhardtMichael Bolte
Jan 15, 2013·The Journal of Physical Chemistry. a·Gulce Ogruc IldizRui Fausto
Jul 17, 2014·The Journal of Physical Chemistry. a·Bernardo A NogueiraRui Fausto
Dec 30, 2014·Acta Crystallographica. Section A, Foundations and Advances·George M Sheldrick
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Mar 19, 2015·Chemical Communications : Chem Comm·Subham Bhattacharjee, Santanu Bhattacharya

❮ 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.