Protomers of benzocaine: solvent and permittivity dependence

Journal of the American Chemical Society
Stephan WarnkeGert von Helden

Abstract

The immediate environment of a molecule can have a profound influence on its properties. Benzocaine, the ethyl ester of para-aminobenzoic acid that finds an application as a local anesthetic, is found to adopt in its protonated form at least two populations of distinct structures in the gas phase, and their relative intensities strongly depend on the properties of the solvent used in the electrospray ionization process. Here, we combine IR-vibrational spectroscopy with ion mobility-mass spectrometry to yield gas-phase IR spectra of simultaneously m/z and drift-time-resolved species of benzocaine. The results allow for an unambiguous identification of two protomeric species: the N- and O-protonated forms. Density functional theory calculations link these structures to the most stable solution and gas-phase structures, respectively, with the electric properties of the surrounding medium being the main determinant for the preferred protonation site. The fact that the N-protonated form of benzocaine can be found in the gas phase is owed to kinetic trapping of the solution-phase structure during transfer into the experimental setup. These observations confirm earlier studies on similar molecules where N- and O-protonation have been ...Continue Reading

References

Sep 22, 2005·Molecular Pharmacology·Gregory M Lipkind, Harry A Fozzard
Jun 19, 2012·Journal of Mass Spectrometry : JMS·Priscila M LalliMarcos N Eberlin
Aug 31, 2012·Journal of the American Chemical Society·Detlef SchröderJana Roithová
Sep 5, 2012·ChemMedChem·Antonio NardiAchim Kless
Sep 8, 2012·Journal of the American Chemical Society·Terrence M ChangEvan R Williams
Oct 8, 2013·Rapid Communications in Mass Spectrometry : RCM·Cris LapthornFrank S Pullen
Jul 10, 2014·Journal of the American Chemical Society·Stephan WarnkeGert von Helden
Aug 20, 2014·Proceedings of the National Academy of Sciences of the United States of America·Céline BoiteuxToby W Allen
Aug 26, 2014·International Journal of Mass Spectrometry·Michael T Bowers

❮ Previous
Next ❯

Citations

Sep 17, 2015·The Journal of Chemical Physics·Antoine MassonThomas R Rizzo
Apr 21, 2016·Journal of the American Society for Mass Spectrometry·J Larry CampbellW Scott Hopkins
Jun 10, 2016·Journal of the American Society for Mass Spectrometry·Neville J A CoughlanEvan J Bieske
Nov 2, 2016·The Journal of Physical Chemistry. a·Edward Matthews, Caroline E H Dessent
Dec 13, 2016·Journal of the American Chemical Society·Jongcheol SeoGert von Helden
Feb 9, 2017·Bioanalysis·Patricia Wright, Christine Eckers
Jan 31, 2017·Journal of the American Chemical Society·Troy J ComiJonathan V Sweedler
Apr 6, 2017·Chemistry, an Asian Journal·Jennifer Anna NobleChristophe Jouvet
Jun 27, 2017·Physical Chemistry Chemical Physics : PCCP·Edward Matthews, Caroline E H Dessent
Feb 18, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Izabella CzerwinskaEdwin De Pauw
Jul 12, 2016·Physical Chemistry Chemical Physics : PCCP·Waldemar HoffmannKevin Pagel
Oct 11, 2016·Physical Chemistry Chemical Physics : PCCP·Jongcheol SeoGert von Helden
Oct 7, 2016·Physical Chemistry Chemical Physics : PCCP·Alyssa GarabedianFrancisco Fernandez-Lima
Jun 3, 2015·Physical Chemistry Chemical Physics : PCCP·Peter B MarkworthEvan J Bieske
Jun 21, 2018·Chemistry : a European Journal·Melanie GöthChristoph A Schalley
Nov 20, 2015·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Aude BouchetOtto Dopfer
Aug 3, 2018·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Christopher KuneEdwin De Pauw
Sep 14, 2018·The Analyst·Eleanor SinclairPerdita Barran
Feb 2, 2019·Mass Spectrometry Reviews·Valérie GabelicaThomas Wyttenbach
Jul 20, 2019·Physical Chemistry Chemical Physics : PCCP·JoAnn C Chen, Rebecca A Jockusch
Sep 15, 2019·Journal of the American Society for Mass Spectrometry·Stephan WarnkeThomas R Rizzo
Jun 13, 2017·Anesthesia Progress·Toshiyuki KishimotoTatsuya Ichinohe
Feb 17, 2018·Physical Chemistry Chemical Physics : PCCP·Jennifer A NobleChristophe Jouvet
Feb 28, 2019·Chemical Science·Eike MuchaKevin Pagel
Mar 21, 2018·Journal of Inherited Metabolic Disease·Jonathan MartensJos Oomens
Feb 20, 2020·Physical Chemistry Chemical Physics : PCCP·Philipp PrachtStefan Grimme

❮ 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.