2016 |
Martinez-Cifuentes, M; Clavijo-Allancan, G; Zuniga-Hormazabal, P; Aranda, B; Barriga, A; Weiss-Lopez, B; Araya-Maturana, R Protonation Sites, Tandem Mass Spectrometry and Computational Calculations of O-Carbonyl Carbazolequinone Derivatives Artículo de revista International Journal of Molecular Sciences, 17 (7), 2016, ISSN: 1422-0067. Resumen | Enlaces | BibTeX | Etiquetas: antitumor assignment, basicities, c-13 carbazole, chemistry complete derivatives, dft, gas-phase hydroquinone ionization, mass molecules, nmr-spectra, qcisd, quinones, respiration, spectrometry, tumor-cell @article{RN321, title = {Protonation Sites, Tandem Mass Spectrometry and Computational Calculations of O-Carbonyl Carbazolequinone Derivatives}, author = { M. Martinez-Cifuentes and G. Clavijo-Allancan and P. Zuniga-Hormazabal and B. Aranda and A. Barriga and B. Weiss-Lopez and R. Araya-Maturana}, url = {/brokenurl#<Go to ISI>://WOS:000381500900086}, doi = {UNSP 1071, 10.3390/ijms17071071}, issn = {1422-0067}, year = {2016}, date = {2016-01-01}, journal = {International Journal of Molecular Sciences}, volume = {17}, number = {7}, abstract = {A series of a new type of tetracyclic carbazolequinones incorporating a carbonyl group at the ortho position relative to the quinone moiety was synthesized and analyzed by tandem electrospray ionization mass spectrometry (ESI/MS-MS), using Collision-Induced Dissociation (CID) to dissociate the protonated species. Theoretical parameters such as molecular electrostatic potential (MEP), local Fukui functions and local Parr function for electrophilic attack as well as proton affinity (PA) and gas phase basicity (GB), were used to explain the preferred protonation sites. Transition states of some main fragmentation routes were obtained and the energies calculated at density functional theory (DFT) B3LYP level were compared with the obtained by ab initio quadratic configuration interaction with single and double excitation (QCISD). The results are in accordance with the observed distribution of ions. The nature of the substituents in the aromatic ring has a notable impact on the fragmentation routes of the molecules.}, keywords = {antitumor assignment, basicities, c-13 carbazole, chemistry complete derivatives, dft, gas-phase hydroquinone ionization, mass molecules, nmr-spectra, qcisd, quinones, respiration, spectrometry, tumor-cell}, pubstate = {published}, tppubtype = {article} } A series of a new type of tetracyclic carbazolequinones incorporating a carbonyl group at the ortho position relative to the quinone moiety was synthesized and analyzed by tandem electrospray ionization mass spectrometry (ESI/MS-MS), using Collision-Induced Dissociation (CID) to dissociate the protonated species. Theoretical parameters such as molecular electrostatic potential (MEP), local Fukui functions and local Parr function for electrophilic attack as well as proton affinity (PA) and gas phase basicity (GB), were used to explain the preferred protonation sites. Transition states of some main fragmentation routes were obtained and the energies calculated at density functional theory (DFT) B3LYP level were compared with the obtained by ab initio quadratic configuration interaction with single and double excitation (QCISD). The results are in accordance with the observed distribution of ions. The nature of the substituents in the aromatic ring has a notable impact on the fragmentation routes of the molecules. |
2016 |
Protonation Sites, Tandem Mass Spectrometry and Computational Calculations of O-Carbonyl Carbazolequinone Derivatives Artículo de revista International Journal of Molecular Sciences, 17 (7), 2016, ISSN: 1422-0067. |