Molecular structure of tryptamine in gas phase according to gas electron diffraction method and quantum chemistry calculations

Marochkin, Ilya I.; Altova, Ekaterina P.; Rykov, Anatolii N.; Shishkov, Igor F.

doi:10.1016/j.molstruc.2017.07.016

Cited by 3 publications

(1 citation statement)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The conformers of TRA have been studied in detail in the gas phase through different experimental techniques. [16][17][18][19][20] The results obtained through theoretical analysis 21 are basically in agreement with the experimental observations. The analysis of the conformational space of TRA were further extended by theoretical studies considering solvent effects.…”

Section: Introductionsupporting

confidence: 75%

Intrinsic Antioxidant Potential of the Aminoindole Structure: A Computational Kinetics Study of Tryptamine

et al. 2018

View full text Add to dashboard Cite

A computational kinetics study of the antioxidant activity of tryptamine toward HO and HOO radicals in water at 298 K has been carried out. Density functional methods have been employed for the quantum chemical calculations, and the conventional transition state theory was used for rate constant evaluation. Different mechanisms have been considered: radical adduct formation (RAF), single electron transfer (SET), and hydrogen atom transfer (HAT). For the reaction of tryptamine with the hydroxyl radical, nearly all channels are diffusion-controlled, and the overall rate constant is very high, 6.29 × 10 M s. The RAF mechanism has a branching ratio of 55%, followed by the HAT mechanism (31%), whereas the SET mechanism accounts just for 13% of the products. The less hindered carbon atom neighboring to the nitrogen of the indole ring seems to be the preferred site for the RAF mechanism, with a branching ratio of 16%. The overall rate constant for the reaction of tryptamine with the HOO radical is 3.71 × 10 M s, suggesting that it could be a competitive process with other reactions of hydroperoxyl radicals in biological environments. For this reaction only the HAT mechanism seems viable. Furthermore, only two centers may contribute to the HAT mechanism, the nitrogen atom of the indole ring and a carbon atom of the aminoethyl chain, the former accounting for more than 91% of the total products. Our results suggest that tryptamine could have a noticeable scavenging activity toward radicals, and that this activity is mainly related to the nitrogen atom of the indole ring, thus showing the relevance of their behavior in the study of aminoindoles.

show abstract

Section: Introductionsupporting

confidence: 75%

Intrinsic Antioxidant Potential of the Aminoindole Structure: A Computational Kinetics Study of Tryptamine

et al. 2018

View full text Add to dashboard Cite

show abstract

Molecules with Ten or More Carbon Atoms

Vogt

2019

Structure Data of Free Polyatomic Molecules

View full text Add to dashboard Cite

Study of bioactive molecular systems by gas-phase electron diffraction: examples, limitations and possibilities

Altova

Rykov

Shishkov

2021

J. Phys.: Conf. Ser.

View full text Add to dashboard Cite

The paper is aimed to the development of structural chemistry of biomolecules, which play essential role for living systems. The structures of biogenic amine, adrenaline, was determined using gas phase electron diffraction (GED) technique in comparison with tryptamine and noradrenaline investigation. Possibilities of method and its limitations are shown in application to bioactive molecular systems. The investigations of the molecules in gas phase allows us to find and describe details of their structures, molecular dynamic which leads to the behavior of the substances in the various processes.

show abstract

Molecular structure of tryptamine in gas phase according to gas electron diffraction method and quantum chemistry calculations

Cited by 3 publications

References 25 publications

Intrinsic Antioxidant Potential of the Aminoindole Structure: A Computational Kinetics Study of Tryptamine

Intrinsic Antioxidant Potential of the Aminoindole Structure: A Computational Kinetics Study of Tryptamine

Molecules with Ten or More Carbon Atoms

Study of bioactive molecular systems by gas-phase electron diffraction: examples, limitations and possibilities

Contact Info

Product

Resources

About