Theoretical studies on tautomerism of tetrazole 5-thion

Chermahini, Alireza Najafi; Teimouri, Abbas; Beni, Alireza Salimi

doi:10.1007/s11224-010-9704-9

Cited by 22 publications

(11 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Table 5 indicates that the induced dipole moments were affected by the change in geometry. This trend was also reported in previous studies [39]. Several such studies point out an increase in the dipole moment when the solute is in polar solvents [1,3,32].…”

Section: Homo-lumo Interaction Energies Dipole Moments and Charge DIsupporting

confidence: 88%

Theoretical and experimental study of solvent effects on the structure, vibrational spectra, and tautomerism of 3-amino-1,2,4-triazine

Yurdakul

Tanrıbuyurdu

2013

Journal of Molecular Structure

View full text Add to dashboard Cite

Section: Homo-lumo Interaction Energies Dipole Moments and Charge DIsupporting

confidence: 88%

Theoretical and experimental study of solvent effects on the structure, vibrational spectra, and tautomerism of 3-amino-1,2,4-triazine

Yurdakul

Tanrıbuyurdu

2013

Journal of Molecular Structure

View full text Add to dashboard Cite

“…In another paper, the tetrazole 5-thione molecule was under consideration and the activation barrier for 1,2-proton transfer was reduced from 53.0 to 23.5 kcal/mol by 1 water molecule at the B3LYP/6-311? ?G(d,p) level of theory [30]. For the tetrazole selenone, the results were similar and 1 water molecule reduced the barrier from 52.8 to 27.3 kcal/mol at the mPW2PLYP/6-311?…”

Section: Introductionmentioning

confidence: 74%

The kinetics of water-assisted tautomeric 1,2-proton transfer in azoles: a computational approach

Ozimiński

2016

Struct Chem

View full text Add to dashboard Cite

A complete set of azoles undergoing 1,2-proton transfer, consisting of pyrazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole and pentazole, was computationally investigated regarding proton transfer mechanism in gas phase and water solution. Complexes of one azole molecule with 1-4 water molecules were employed to facilitate the proton transfer by lowering the activation energy, which for the isolated azole molecule is prohibitively large. The calculations were performed at the MP2/aug-cc-pVDZ and B3LYP/6-311??G(d,p) levels of theory which showed very good concordance. It follows that in the most probable transition state one azole molecule is accompanied by two water molecules. The activation barrier in water solution modelled by PCM method was lowered to 18.8 kcal/mol in the case of pyrazole and more for azoles containing more nitrogen atoms in the ring, reaching 6.8 kcal/mol in the case of pentazole. The analysis of the IRC reaction paths showed that proton transfer in the gas phase has more synchronous character and in the water solution is rather stepwise. It also follows from the analysis of bond lengths in the transition state that in the case of pyrazole the transition state is more cation-like and for other azoles, especially pentazole, is more anion-like. In the water environment, the initial step of proton transfer is moving the proton from azole to the water cluster in all cases except pyrazole, where the proton moves first from the water cluster to the azole molecule.

show abstract

“…ΔH=Ea-RT R = 0.001987 kcal/K mol (1) Ea= ΔH+ RT= ΔH+(0.001987)298 = ΔH+ 0.59 (kcal/mol) The activation energies in the gas phase for proton transfer reaction of B→A reaction in the gas phase were measured using DFT and MP2 methods by 6-311+G(d) basis function [19]. The results of this measurement was reported in Table 4.…”

Section: Resultsmentioning

confidence: 99%

Theoretical studies of ethylnitrolic acid using Gaussian

Nikafshar

Mirazizi

2017

J. Fundam and Appl Sci.

View full text Add to dashboard Cite

The tautomerism of all possible forms of ethylnitrolic acid was investigated theoretically in various environment including gas phase, ethanol, dimethyl sulfoxide (DMSO) and water.The calculations were carried out at DFT/B3LYP and MP 2 of theory singly. It was found that, form of B eythynitrolic acid is the most stable isomer in the both gas phase and solvent. The activation energies for conversion of A to R and B to A in the gas phase and solvent using two methods DFT/B3LY and MP 2 were obtained. Geometrical parameters of three isomers, A, B and R, were calculated by (DFT/B3LYP and MP 2 ) in the gas phase and solvent. Vibrational analysis and acidity constants (PK a ) of two isomers (A and R) were computed in the gas phase and water using DFT/B3LYP and MP 2 . After that, these quantities were evaluated with experimental values and it was determined that DFT/B3LYP is more accurate to obtain PK a .

show abstract

Theoretical studies on tautomerism of tetrazole 5-thion

Cited by 22 publications

References 32 publications

Theoretical and experimental study of solvent effects on the structure, vibrational spectra, and tautomerism of 3-amino-1,2,4-triazine

Theoretical and experimental study of solvent effects on the structure, vibrational spectra, and tautomerism of 3-amino-1,2,4-triazine

The kinetics of water-assisted tautomeric 1,2-proton transfer in azoles: a computational approach

Theoretical studies of ethylnitrolic acid using Gaussian

Contact Info

Product

Resources

About