A quantum-mechanical study of the influence of excitation and solvation on the tautomeric equilibrium of tetrazole

Rażyńska, Anna; Tempczyk, Anna; Grzonka, Zbigniew

doi:10.1039/f29858101555

Cited by 12 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The free N-H bond of tetrazoles makes them acidic molecules because of the ability of the moiety to stabilize a negative charge by electron delocalization. Tetrazolate anionic species are more reactive than the corresponding neutral species toward a variety of electrophiles and alkylating agents [15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Regioselective and Stereoselective Addition of Tetrazole Derivatives to Electron‐poor Acetylenic Esters in the Presence of Triphenylphosphine

Ramazani

Nasrabadi

Ślepokura

et al. 2015

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Protonation of the highly reactive 1:1 intermediates produced in the reaction between triphenylphosphine and acetylenic esters by tetrazole derivatives leads to the formation of vinyltriphenylphosphonium salts. The cation of these salts undergoes an addition reaction with the counter anion in CH2Cl2 at room temperature to yield the corresponding stabilized phosphorus ylides. Elimination of triphenylphosphine from the stabilized phosphorus ylides leads to the corresponding electron‐poor N‐vinyl tetrazoles in fairly high yields. Structures of N‐vinyl tetrazoles were determined by IR, 1H NMR, 13C NMR and single crystal X‐ray structure analyses. The reaction is fairly regioselective and stereoselective.

show abstract

Section: Introductionmentioning

confidence: 99%

Regioselective and Stereoselective Addition of Tetrazole Derivatives to Electron‐poor Acetylenic Esters in the Presence of Triphenylphosphine

Ramazani

Nasrabadi

Ślepokura

et al. 2015

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…The recent theoretical study [14] on both the free and solvated molecules has virtually revealed that in the lowest excited singlet state the tautomeric equilibrium is displaced well in favour of the 2H-tautomer.…”

Section: Mean Lifetimes Of Fluorescencementioning

confidence: 99%

Luminescence of 5-Phenyltetrazole and its Derivatives Part III. Quantum Yields and Mean Lifetimes of Fluorescence

Gryczyński

Kawski

1984

Zeitschrift Für Naturforschung A

View full text Add to dashboard Cite

L u m in escen ce o f 5 -P h e n y lte tr a z o le a n d its D e riv a tiv e s P a r t III.Q u a n tu m Y ie ld s a n d M e a n L ife tim e s o f F lu o r e s c e n c e I. Gryczyński and A. Kawski Luminescence Research Group, Institute of Experimental Physics, University of Gdansk, Gdansk, Poland A Rażyńska and Z. Grzonka Institute of Chemistry. University of Gdansk, Gdansk, Poland Z. Naturforsch. 39a, 960-962 (1984); received August 9, 1984 Quantum yields and mean lifetimes of fluorescence have been measured of 5-phenyltetrazole and its three methyl derivatives, para-, meta-and ortho-methyl-5-phenyltetrazole. The rate constants, k¥, of the radiative transition Sj -»• S0 have been deduced from these measurements. The mean lifetimes, rF, the quantum yields of fluorescence and the rate con stants have been found to be clearly dependent on the position of the methyl substituent in the ring and could be arranged as follows: tp > tp1 > tf and > k? > .

show abstract

“…X-ray [54] 1.32 (2) 1.34 (2) 1.29 (2) 1.32 (2) 1. 35 (2) 1.310 (2) 1.348 (2) 1.329 (3) 112.5 (2) 104.3 (2) 109.5 (2) 109.5 (2) 104.3 (2) diffraction [55] tetrazolate monohydrate [56] 30 X-ray [57] 1.290 (13) 1.345 (13) 1.283 (13) 1.347 (13) 1.351 (14) 111.4 (9) 104.2 (9) 112.2 (9) 106.9 (9) 105.3 (9) calculated and experimental data show that the tetrazole cycle is practically planar and is characterized by the stability of the geometrical structure of the nature of substituents in both C and N positions. Introduction of voluminous (rerr-butyl-, phenyl-, isopropyl-) substituents into the cycle does not affect its geometry.…”

mentioning

confidence: 99%

Comparative semiempirical calculations of tetrazole derivatives

Ивашкевич

Гапоник

Koren

et al. 1992

Int J of Quantum Chemistry

View full text Add to dashboard Cite

Heats of formation, protonation energies, charge distributions, dipole moments, and geometrical structures of thirty-two 1-, 2-, 1,5-, and 2,5-substituted tetrazoles have been investigated by different semiempirical SCF MO calculations. MNW and, in some cases, AM^ methods are the most acceptable for tetrazole derivatives. A number of linear correlations between available experimental data and the calculated energies and charge characteristics have been established. 0 1992

show abstract

A quantum-mechanical study of the influence of excitation and solvation on the tautomeric equilibrium of tetrazole

Cited by 12 publications

References 0 publications

Regioselective and Stereoselective Addition of Tetrazole Derivatives to Electron‐poor Acetylenic Esters in the Presence of Triphenylphosphine

Regioselective and Stereoselective Addition of Tetrazole Derivatives to Electron‐poor Acetylenic Esters in the Presence of Triphenylphosphine

Luminescence of 5-Phenyltetrazole and its Derivatives Part III. Quantum Yields and Mean Lifetimes of Fluorescence

Comparative semiempirical calculations of tetrazole derivatives

Contact Info

Product

Resources

About