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Theoretical investigation on the water-assisted excited-state proton transfer of 7-azaindole derivatives: substituent effect

Yi, Jiacheng ; Fang, Hua

Journal of molecular modeling, 2017-11, Vol.23 (11), p.312-11, Article 312 [Periódico revisado por pares]

Berlin/Heidelberg: Springer Berlin Heidelberg

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  • Título:
    Theoretical investigation on the water-assisted excited-state proton transfer of 7-azaindole derivatives: substituent effect
  • Autor: Yi, Jiacheng ; Fang, Hua
  • Assuntos: Characterization and Evaluation of Materials ; Chemistry ; Chemistry and Materials Science ; Computer Appl. in Life Sciences ; Computer Applications in Chemistry ; Molecular Medicine ; Nitrogen dioxide ; Original Paper ; Protons ; Reaction kinetics ; Theoretical and Computational Chemistry
  • É parte de: Journal of molecular modeling, 2017-11, Vol.23 (11), p.312-11, Article 312
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: A systematic study on the first excited-state proton transfer (ESPT) in 2RAI-H 2 O (R = OH, OCH 3 , CN, NO 2 , CHO) complexes in solution were investigated at the TD-M06-2X/6-31 + G(d, p) level. The double proton transfer occurred in an asynchronous but concerted protolysis fashion no matter which substituent R was used at C 2 position in pyrrole ring in the 7AI-H 2 O complex. The specific vibrational-mode of ESPT in the model systems was confirmed and contributed to promote the reaction rate by shortening the reaction path. The substituent effects of different groups on the ESPT thermodynamics and kinetics were discussed. It was obvious that the geometries, barrier height, asynchrony, and specific vibration-mode of excited-state proton transfer changed with the different substituent groups. Graphical Abstract The distance between two neighboring heavy atoms such as N 1 -O 11 (R 1 ) and O 11 -N 8 (R 2 ) distances played an important role in the proton transfer reaction. The sum of the N 1 -O 11 and O 11 -N 8 distances in the reactant of 2RAI-H 2 O (R=H, OH, OCH 3 ; CN, CHO, NO 2 ) complexes is in the range of 5.542 Å~5.692 Å and changes along with the substituent group at C 2 position in the pyrrole ring. The ESDPT barrier height and the sum of the N 1 -O 11 and O 11 -N 8 distances have a good correlation.
  • Editor: Berlin/Heidelberg: Springer Berlin Heidelberg
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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