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Protonation behaviour of 2-phenyl-1,3-diazaazulene derivatives
- Source :
- Tetrahedron. 74:731-739
- Publication Year :
- 2018
- Publisher :
- Elsevier BV, 2018.
-
Abstract
- Three 2-phenyl-1,3-diazaazulene derivatives were synthesized and their protonation behaviours were investigated systematically via UV–vis absorption titration and 1H NMR titration, as well as theoretical calculations. One of them exhibited a monoprotonation process while the others displayed prominent halochromic diprotonation responses. Interestingly, upon protonation of 2-phenyl-1,3-diazaazulene derivatives, the coplanarity and conjugation of the 16-π-conjugated backbones were well kept, while the electronic structures were controllably adjusted. The response mechanism of 1,3-diazaazulene derivatives towards acid is through the attachment of acid proton to the nitrogen atom in the diazaazulene ring, resulting in the change of the hybridization of protonated-N from sp2 to sp3, which differed from that of the well-known azulene (analogue of 1,3-diazaazulene, protonation at carbon atom). This work would provide a new insight into the protonation research of the organic functional molecules.
- Subjects :
- Proton
Chemistry
Organic Chemistry
Protonation
02 engineering and technology
Azulene
010402 general chemistry
021001 nanoscience & nanotechnology
Ring (chemistry)
01 natural sciences
Biochemistry
0104 chemical sciences
chemistry.chemical_compound
Functional importance
Computational chemistry
Drug Discovery
Proton NMR
Titration
Absorption (chemistry)
0210 nano-technology
Subjects
Details
- ISSN :
- 00404020
- Volume :
- 74
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........5b395f36ee189cff4fc1ab3275fcb8d5
- Full Text :
- https://doi.org/10.1016/j.tet.2017.12.051