Theoretical study of the tautomeric equilibrium of 4(1H)-pyridinone in solution

1985 ◽  
Vol 107 (25) ◽  
pp. 7569-7572 ◽  
Author(s):  
J. A. Sordo ◽  
M. Klobukowski ◽  
Serafin Fraga
Keyword(s):  
Theoretical Study ◽  
Tautomeric Equilibrium

scholarly journals Tautomeric Equilibrium Modeling: Stability and Reactivity of Benzothiazole and Derivatives

2019 ◽  
Vol 11 (1) ◽  
pp. 84
Author(s):  
Lucie A. Bédé ◽  
Mawa Koné ◽  
Guy R. M. Koné ◽  
Simplice C. S. Ouattara ◽  
Lamoussa Ouattara ◽  
...  
Keyword(s):  
Public Health ◽  
Large Scale ◽  
Theoretical Study ◽  
Biological Activities ◽  
Tautomeric Equilibrium ◽  
Equilibrium Modeling ◽  
Benzothiazole Derivatives ◽  
Global Indices ◽  
Thiol Form ◽  
Industrial Level

Benzothiazoles are organic compounds with multiple biological activities. Due to their biological interests, these are synthesized on a large scale at the industrial level and used in various fields. Their release into waters causes environmental problems which leads to public health problems. Finding solution which can help for their degradation become necessary. That is the reason why a theoretical study of the reactivity of five benzothiazole derivatives has been initiated in order to understand some aspect of their biodegradation. The calculations were carried out in gaseous and aqueous phase with B3LYP functional associated with bases 6-311G(d) and 6-31+G(d). The results revealed that the thione tautomer of the MBT derivative is more stable than the thiol form. These results are in agreement with previous experimental work which showed that the thiones forms in MBT metal complexes are the most stable. Moreover, the study of the reactivity based on the computation of the global indices of reactivity reveals that the benzothiazoles BT, OBT and MBT are the most reactive. The most electrophilic is BT and the least electrophilic is MTBT. In addition, the thermodynamic parameters and the energy barriers predict a possibility of coexistence of tautomers ol and one of OBT derivative. Fukui dual descriptors have shown that the carbon C2 of BT is the most electrophilic. In substituted derivatives, it is the C6 carbon that is the most electrophilic. N3 nitrogen remains the most nucleophilic site in all the studied molecules.

Benzotriazolium ylides: Experimental and theoretical study on the tautomeric equilibrium of monosubstituted benzotriazolium ylides

2003 ◽  
Vol 81 (5) ◽  
pp. 350-356 ◽  
Author(s):  
Neculai Doru Miron ◽  
Patrice Woisel ◽  
Georgiana G Surpateanu ◽  
Gérard Vergoten ◽  
Ludovic Depature ◽  
...  
Keyword(s):  
Theoretical Analysis ◽  
Theoretical Study ◽  
Tautomeric Equilibrium ◽  
Semiempirical Calculations ◽  
Dynamic Nmr ◽  
Nmr Analysis ◽  
Tautomeric Forms ◽  
Synthetic Procedure

The biphenacyl benzotriazolium salts 12 give a tautomeric equilibrium 13[Formula: see text]14 in the presence of triethylamine (TEA) or NaOH. The evaluation of this tautomeric equilibrium has been studied using a dynamic NMR analysis and a new synthetic procedure of disubstituted benzotriazolium ylides 15 and 16, which have in their structures a picryl fragment. This study also includes a theoretical analysis on the reactivity of salts 12a–c and the thermodynamical stability of tautomeric forms 13 and 14 by AM1 and PM3 procedure methods.Key words: synthesis, salts, ylides, semiempirical calculations, kinetics.

Synthesis, Experimental and Theoretical Study on the Structure of Some Semicarbazides with Potential Antibacterial Activity

2011 ◽  
Vol 66 (5) ◽  
pp. 505-511 ◽  
Author(s):  
Monika Pitucha ◽  
Zbigniew Karczmarzyk ◽  
Urszula Kosikowska ◽  
Anna Malm
Keyword(s):  
Antibacterial Activity ◽  
Gas Phase ◽  
Elemental Analysis ◽  
Active Compound ◽  
Spectroscopic Data ◽  
Model Compound ◽  
Tautomeric Form ◽  
Theoretical Study ◽  
Tautomeric Equilibrium ◽  
New Compounds

A series of 1,4-disubstituted semicarbazide and 4,4’-bis[1-substituted semicarbazide]diphenylmethane derivatives were synthesized to explore their antibacterial activity. New compounds were characterized by elemental analysis and spectroscopic data. In order to find the tautomeric equilibrium for the molecules energy calculations for each possible tautomeric form of model compound 2, and for the most antibacterially active compound 7 in the investigated series, were calculated for the gas phase at the RHF/SCF/6-31G** level of theory

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