4-Hydroxy-1-naphthaldehydes: proton transfer or deprotonation

Physical Chemistry Chemical Physics : PCCP
Y ManolovaPoul Erik Hansen

Abstract

A series of naphthaldehydes, including a Mannich base, have been investigated by UV-Vis spectroscopy, NMR and theoretical methods to explore their potential tautomerism. In the case of 4-hydroxy-1-naphthaldehyde concentration dependent deprotonation has been detected in methanol and acetonitrile. For 4-hydroxy-3-(piperidin-1-ylmethyl)-1-naphthaldehyde (a Mannich base) an intramolecular proton transfer involving the OH group and the piperidine nitrogen occurs. In acetonitrile the equilibrium is predominantly at the OH-form, whereas in methanol the proton transferred tautomer is the preferred form. In chloroform and toluene, the OH form is completely dominant. Both 4-hydroxy-1-naphthaldehyde and 4-methoxy-1-naphthaldehyde (fixed enol form) show dimerization in the investigated solvents and the crystallographic data, obtained for the latter, confirm the existence of a cyclic dimer.

References

Jan 5, 2002·Chemical Reviews·Ben L. FeringaEdzard M. Geertsema
Dec 11, 2002·Analytical and Bioanalytical Chemistry·Liudmil Antonov, Vesselin Petrov
Jul 11, 2003·Nature·David A LeighFrancesco Zerbetto
Apr 29, 2004·Journal of the American Chemical Society·Peter M TolstoyHans-Heinrich Limbach
Aug 12, 2005·Chemical Reviews·Jacopo TomasiRoberto Cammi
Sep 28, 2005·Physical Chemistry Chemical Physics : PCCP·Pedro D VazPaulo J A Ribeiro-Claro
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jan 12, 2008·Accounts of Chemical Research·Yan Zhao, Donald G Truhlar
Sep 17, 2009·Angewandte Chemie·Liudmil AntonovJakob Wirz
Mar 11, 2011·Journal of Physics. Condensed Matter : an Institute of Physics Journal·Sense Jan van der Molen, Peter Liljeroth
Sep 2, 2011·Physical Chemistry Chemical Physics : PCCP·Denis JacqueminCarlo Adamo
Mar 1, 2012·Nature Nanotechnology·Fabian MohnGerhard Meyer
Mar 20, 2012·Chemical Society Reviews·Manuel Natali, Silvia Giordani
Apr 21, 2012·Chemistry : a European Journal·Aleksandar R TodorovJuho Helaja
Dec 10, 2014·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Liudmil AntonovCarlo Adamo

❮ Previous
Next ❯

Citations

Apr 1, 1961·The American Journal of Cardiology·S JARCHO
Jul 8, 2015·Journal of the American Chemical Society·Lior SepunaruDavid Cahen
May 5, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tareq Irshaidat
Oct 20, 2018·Journal of Fluorescence·Nurcan TuncerCanan Unaleroglu
Jan 17, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Atena B SoleaOlimpia Mamula
Aug 31, 2019·Beilstein Journal of Organic Chemistry·Vera DenevaLiudmil Antonov
Sep 28, 2017·Physical Chemistry Chemical Physics : PCCP·H MarciniakL Antonov

❮ 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.