Tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ N ⟶ BF 2 fluorescent dyes
Abstract The stability of two groups of conformationally locked molecules, similar in topology, but differing only by the type of the bridge rigidifying their structure, is studied. The series of the less-rigid 2-phenacylheterocyclic compounds and their stiff difluoroboranyl derivatives are investig...
Guardado en:
| Autores principales: | , , |
|---|---|
| Formato: | article |
| Lenguaje: | EN |
| Publicado: |
Nature Portfolio
2021
|
| Materias: | |
| Acceso en línea: | https://doaj.org/article/1dfe6c6146b344c88406a56ed67c6d92 |
| Etiquetas: |
Agregar Etiqueta
Sin Etiquetas, Sea el primero en etiquetar este registro!
|
| id |
oai:doaj.org-article:1dfe6c6146b344c88406a56ed67c6d92 |
|---|---|
| record_format |
dspace |
| spelling |
oai:doaj.org-article:1dfe6c6146b344c88406a56ed67c6d922021-12-02T17:06:32ZTautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ N ⟶ BF 2 fluorescent dyes10.1038/s41598-021-94978-92045-2322https://doaj.org/article/1dfe6c6146b344c88406a56ed67c6d922021-08-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-94978-9https://doaj.org/toc/2045-2322Abstract The stability of two groups of conformationally locked molecules, similar in topology, but differing only by the type of the bridge rigidifying their structure, is studied. The series of the less-rigid 2-phenacylheterocyclic compounds and their stiff difluoroboranyl derivatives are investigated for the determination of the effect of $$\hbox {NCH}_3$$ NCH 3 /S/O replacement in a five-membered heterocyclic ring and the presence of a strong electron-donating group on the tautomeric equilibrium, protonation affinity, and fragmentation pattern observed in the structural elucidation by means of mass spectrometry technique. The results of the $$\omega $$ ω B97X-D/6-311++G(d,p) calculations, the topological analysis of electron density as well as the experimental MS measurements show the importance of the number of heteroatoms, their properties, and location in the molecule for the rational design of the systems of desired stable tautomers or the favorable protonation sites. The obtained data allow for the understanding of the fundamentals of the novel highly fluorescent difluoroborates fragmentation behavior, vital for their structural elucidation with the application of high-resolution tandem mass spectrometry methods.Małgorzata A. KaczorowskaAnna Kaczmarek-KędzieraBorys OśmiałowskiNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-14 (2021) |
| institution |
DOAJ |
| collection |
DOAJ |
| language |
EN |
| topic |
Medicine R Science Q |
| spellingShingle |
Medicine R Science Q Małgorzata A. Kaczorowska Anna Kaczmarek-Kędziera Borys Ośmiałowski Tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ N ⟶ BF 2 fluorescent dyes |
| description |
Abstract The stability of two groups of conformationally locked molecules, similar in topology, but differing only by the type of the bridge rigidifying their structure, is studied. The series of the less-rigid 2-phenacylheterocyclic compounds and their stiff difluoroboranyl derivatives are investigated for the determination of the effect of $$\hbox {NCH}_3$$ NCH 3 /S/O replacement in a five-membered heterocyclic ring and the presence of a strong electron-donating group on the tautomeric equilibrium, protonation affinity, and fragmentation pattern observed in the structural elucidation by means of mass spectrometry technique. The results of the $$\omega $$ ω B97X-D/6-311++G(d,p) calculations, the topological analysis of electron density as well as the experimental MS measurements show the importance of the number of heteroatoms, their properties, and location in the molecule for the rational design of the systems of desired stable tautomers or the favorable protonation sites. The obtained data allow for the understanding of the fundamentals of the novel highly fluorescent difluoroborates fragmentation behavior, vital for their structural elucidation with the application of high-resolution tandem mass spectrometry methods. |
| format |
article |
| author |
Małgorzata A. Kaczorowska Anna Kaczmarek-Kędziera Borys Ośmiałowski |
| author_facet |
Małgorzata A. Kaczorowska Anna Kaczmarek-Kędziera Borys Ośmiałowski |
| author_sort |
Małgorzata A. Kaczorowska |
| title |
Tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ N ⟶ BF 2 fluorescent dyes |
| title_short |
Tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ N ⟶ BF 2 fluorescent dyes |
| title_full |
Tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ N ⟶ BF 2 fluorescent dyes |
| title_fullStr |
Tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ N ⟶ BF 2 fluorescent dyes |
| title_full_unstemmed |
Tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ N ⟶ BF 2 fluorescent dyes |
| title_sort |
tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {n}\longrightarrow \hbox {bf}_2$$ n ⟶ bf 2 fluorescent dyes |
| publisher |
Nature Portfolio |
| publishDate |
2021 |
| url |
https://doaj.org/article/1dfe6c6146b344c88406a56ed67c6d92 |
| work_keys_str_mv |
AT małgorzataakaczorowska tautomericequilibriumprotonaffinityandmassspectrometryfragmentationofflexiblehydrogenbondedprecursorsandrigidhboxnlongrightarrowhboxbf2nbf2fluorescentdyes AT annakaczmarekkedziera tautomericequilibriumprotonaffinityandmassspectrometryfragmentationofflexiblehydrogenbondedprecursorsandrigidhboxnlongrightarrowhboxbf2nbf2fluorescentdyes AT borysosmiałowski tautomericequilibriumprotonaffinityandmassspectrometryfragmentationofflexiblehydrogenbondedprecursorsandrigidhboxnlongrightarrowhboxbf2nbf2fluorescentdyes |
| _version_ |
1718381541646663680 |