Theoretical Study of the Proton Transfer in Enaminones
TLDR
In this article, the three possible tautomers of eneminones were fully optimized at several theoretical levels including B3LYP with the 6-31+G(d,p), 6-311++G(D,p) and aug-cc-pVDZ basis sets.Abstract:
Problem statement: Hydrogen bonding has a vital rule to unrevealed the nature of many different interactions both in gas phase and condensed media thus it is one of the most important concepts in chemistry. Enaminoes with their ability to form intrahydrogen bonded cheated rings represent one of the suitable compounds to study such concept. Approach: The three possible tautomers of eneminones were fully optimized at several theoretical levels including B3LYP with the 6-31+G(d,p), 6-311++G(d,p) and aug-cc-pVDZ basis sets as well as MP2/6-311++G(d,p) level of theory. Then a search for the possible transition state between the two most stable tautomers; the ketamine and the enolimine was done at the B3LYP/6-311++G(d,p) level of theory. Results: The ketamine is the most stable while the diketo is the less stable within the tautomeric mixture and the proton transfer occurs through a transition state that is energetically resemble the enolimine tautomer. Conclusion: The interconversion of the tautomers is preferable in the enolimine → ketamine direction.read more
Citations
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Electronic structures, intramolecular hydrogen bond interaction, and aromaticity of substituted 4-amino-3-penten-2-one in ground and electronic excited state
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Synthesis of 3-( N -arylcarbamoyl)chromones from 2-hydroxyarylaminoenones and isocyanates
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Studying the geometric parameters, stability of isomer and IR frequencies in enaminone compounds with the DFT and HF methods: A theoretical study
TL;DR: In this article, Sustainability and inter-molecular hydrogen bond strength of each isomer of enaminone is investigated and the results of calculations in geometry parameters indicated that in their parameters, B3P86 method and 6-311++G** basis set have considerable preference than other methods and basis sets.
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References
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Evidence for Intramolecular N−H···O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation
TL;DR: The resonance-assisted hydrogen bond (RAHB) is a model of synergistic interplay between π-delocalization and hydrogen-bond strengthening originally introduced by Gilli, G. as discussed by the authors.
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Enaminones: versatile intermediates for natural product synthesis*
Joseph P. Michael,C. B. De Koning,David Gravestock,Gladys D. Hosken,Arthur S. Howard,C. M. Jungmann,Rui W. M. Krause,Andrew S. Parsons,Stephen C. Pelly,Trevor V. Stanbury +9 more
TL;DR: In this article, an overview of the chemistry of enaminones and related compounds containing the structural unit N-CaC-Z (Za COR, CO2R, CN, NO2, S O 2Ar, etc.).
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Anticonvulsant evaluation and mechanism of action of benzylamino enaminones.
TL;DR: The most potent enaminone in this series was the unsubstituted benzylamine analog (30; methyl 4-benzylamino-6-methyl-2-oxocyclohex-3-en-1-oate), which had an oral effective dose (ED50) in rats of 27 mg/kg against maximal electroshock seizures.
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Enaminone amides as novel orally active GABAA receptor modulators.
Derk J. Hogenkamp,Timothy B C Johnstone,Jin-Cheng Huang,Wen-Yen Li,Minhtam B. Tran,Edward R. Whittemore,Rudy E. Bagnera,Kelvin W. Gee +7 more
TL;DR: Structural-activity relationship (SAR) studies resulted in the synthesis of the c-Bu amide 16h with an in vitro potency of 7 nM based on inhibition of [35S]TBPS binding, which was an orally active anxiolytic in the mouse light-dark paradigm.
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Studies with enaminones: The reaction of enaminones with aminoheterocycles. A route to azolopyrimidines, azolopyridines and quinolines
TL;DR: The enaminones 1b,d,f react with 4-phenyl-3-methyl-5-pyrazoleamine 3a to yield the pyrazole derivatives 4a-c that cyclised readily on reflux in pyridine solution in presence of hydrochloric acid as mentioned in this paper.