Gas-phase acid-base properties of melamine and cyanuric acid.

Journal of the American Society for Mass Spectrometry
Sumit Mukherjee, Jianhua Ren

Abstract

The thermochemical properties of melamine and cyanuric acid were characterized using mass spectrometry measurements along with computational studies. A triple-quadrupole mass spectrometer was employed with the application of the extended Cooks kinetic method. The proton affinity (PA), gas-phase basicity (GB), and protonation entropy (Δ(p)S) of melamine were determined to be 226.2 ± 2.0 kcal/mol, 218.4 ± 2.0 kcal/mol, and 26.2 ± 2.0 cal/mol K, respectively. The deprotonation enthalpy (Δ(acid)H), gas-phase acidity (Δ(acid)G), and deprotonation entropy (Δ(acid)S) of cyanuric acid were determined to be 330.7 ± 2.0 kcal/mol, 322.9 ± 2.0 kcal/mol, and 26.1 ± 2.0 cal/mol K, respectively. The geometries and energetics of melamine, cyanuric acid, and related ionic species were calculated at the B3LYP/6-31+G(d) level of theory. The computationally predicted proton affinity of melamine (225.9 kcal/mol) and gas-phase deprotonation enthalpy of cyanuric acid (328.4 kcal/mol) agree well with the experimental results. Melamine is best represented as the imide-like triazine-triamine form and the triazine nitrogen is more basic than the amino group nitrogen. Cyanuric acid is best represented as the keto-like tautomer and the N-H group is the mos...Continue Reading

References

Sep 15, 1988·Physical Review A: General Physics·A D Becke
May 3, 2000·Journal of the American Society for Mass Spectrometry·P B Armentrout
May 22, 2002·Journal of the American Society for Mass Spectrometry·Kent M Ervin
Feb 1, 2003·The Journal of Organic Chemistry·Maria ArduiniDavid N Reinhoudt
Sep 24, 2004·Journal of Mass Spectrometry : JMS·László DrahosKároly Vékey
Sep 24, 2004·Journal of Mass Spectrometry : JMS·Kent M Ervin, P B Armentrout
Sep 24, 2004·Journal of Mass Spectrometry : JMS·Guy BouchouxFlorence Berruyer-Penaud
Jan 25, 2006·Chemical Communications : Chem Comm·Luís M A PerdigãoPeter H Beton
Jul 21, 2006·The Journal of Physical Chemistry. B·D VollhardtF Liu
Nov 14, 2007·Journal of Veterinary Diagnostic Investigation : Official Publication of the American Association of Veterinary Laboratory Diagnosticians, Inc·Birgit PuschnerPatricia A Pesavento
Feb 22, 2008·The Journal of Physical Chemistry. B·Guy BouchouxRosa Ngo Biboum Bimbong
Aug 12, 2008·Toxicological Sciences : an Official Journal of the Society of Toxicology·Roy L M DobsonGeorge P Daston
Sep 16, 2008·Journal of the American Society for Mass Spectrometry·Francoise FournierJean-Claude Tabet
Jan 28, 2009·Clinica Chimica Acta; International Journal of Clinical Chemistry·Ching-Wan LamPaul Kwong-Hang Tam
Mar 14, 2009·Chemical Communications : Chem Comm·Guangming HuangR Graham Cooks
May 30, 2009·The Journal of Physical Chemistry. a·Guy BouchouxFadila Nacer
Sep 17, 2009·The Journal of Physical Chemistry. a·Jianhua RenRobert T Harper
Dec 25, 2009·Microscopy and Microanalysis : the Official Journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada·Ryna B MarinenkoJohn A Small
Apr 1, 1947·Journal of the American Chemical Society·I M KLOTZ, T ASKOUNIS

❮ Previous
Next ❯

Citations

Sep 29, 2011·Journal of the American Society for Mass Spectrometry·John M GarverVeronica M Bierbaum
Jun 21, 2013·Environmental Science & Technology·Jeremy J B WentzellJeffrey R Brook
Jan 25, 2011·Physical Chemistry Chemical Physics : PCCP·D VollhardtS Dutta Banik
Jul 6, 2015·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Igor Reva
Oct 16, 2016·Chemical Reviews·Ewa D RaczyńskaPierre-Charles Maria
Oct 13, 2012·Chemistry : a European Journal·Ana Martín-SómerJean-Claude Guillemin
Aug 16, 2017·Journal of Molecular Modeling·Andre N PetelskiGladis L Sosa

❮ 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.

Related Papers

Journal of Mass Spectrometry : JMS
Andreina RicciPierluigi Giacomello
The Journal of Physical Chemistry. B
David TouboulRenato Zenobi
© 2021 Meta ULC. All rights reserved