Using Terahertz Spectroscopy and Solid-State Density Functional Theory to Characterize a New Polymorph of 5-(4-pyridyl)tetrazole

Pellizzeri, Steven; Delaney, Sean P.; Korter, Timothy M.; Zubieta, Jon

doi:10.1021/jp412142w

Cited by 17 publications

(21 citation statements)

References 34 publications

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“…As a result, determination of the temperature influence on the structural properties as well as description of volume-dependent thermal features is possible. Many results confirm that such an approach distinctly enhances the quality of the obtained vibrational spectra [180,181].…”

Section: Vibrational Propertiessupporting

confidence: 54%

Periodic DFT Calculations—Review of Applications in the Pharmaceutical Sciences

2020

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In the introduction to this review the complex chemistry of solid-state pharmaceutical compounds is summarized. It is also explained why the density functional theory (DFT) periodic calculations became recently so popular in studying the solid APIs (active pharmaceutical ingredients). Further, the most popular programs enabling DFT periodic calculations are presented and compared. Subsequently, on the large number of examples, the applications of such calculations in pharmaceutical sciences are discussed. The mentioned topics include, among others, validation of the experimentally obtained crystal structures and crystal structure prediction, insight into crystallization and solvation processes, development of new polymorph synthesis ways, and formulation techniques as well as application of the periodic DFT calculations in the drug analysis.

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Section: Vibrational Propertiessupporting

confidence: 54%

Periodic DFT Calculations—Review of Applications in the Pharmaceutical Sciences

2020

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“…168 Succinonitrile forms a plastic crystal that is flexible and exhibits strong disorder in its crystalline phase at room temperature but that can be ''frozen out'' at lower temperature, leading to a much more ordered, rigid-crystal phase that exhibits distinct, albeit broad, spectra features at terahertz frequencies. 169 This study made a nice connection among the spectra originating from well-defined crystal structures; slightly disordered systems such as benzoic acid, where symmetry breaking is observed; 170 and the even more disordered LCs discussed earlier.…”

Section: Crystalline Systemsmentioning

confidence: 99%

Terahertz Time-Domain and Low-Frequency Raman Spectroscopy of Organic Materials

2015

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With the ongoing proliferation of terahertz time-domain instrumentation from semiconductor physics into applied spectroscopy over the past decade, measurements at terahertz frequencies (1 THz [ 10 12 Hz [ 33 cm À1) have attracted a sustained growing interest, in particular the investigation of hydrogen-bonding interactions in organic materials. More recently, the availability of Raman spectrometers that are readily able to measure in the equivalent spectral region very close to the elastic scattering background has also grown significantly. This development has led to renewed efforts in performing spectroscopy at the interface between dielectric relaxation phenomena and vibrational spectroscopy. In this review, we briefly outline the underlying technology, the physical phenomena governing the light-matter interaction at terahertz frequencies, recent examples of spectroscopic studies, and the current state of the art in assigning spectral features to vibrational modes based on computational techniques.

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“…As the vibrational properties are very sensitive to the lattice vectors, it is important to optimize the crystal's structure to a better accuracy by including various interatomic interactions. 35,48 Hence, to capture the weak interlayer nonbonded interactions [van der Waals (vdW), hydrogen bond], we optimized all the crystal structures with the dispersion-corrected Grimme functional, that is, PBE + G06. 36 The obtained results show very good agreement with the experimental data, and the deviations of all of the obtained lattice vectors, volumes, and β values are around ∼1% (see Table 2).…”

Section: Acs Omegamentioning

confidence: 99%

“…[6][7][8][9][10]27,28 However, most of the reported tetrazole derivatives are very sensitive to impact and friction. 11−13 Pellizzeri et al 35 reported the polymorphic characterization of 5(4-pyridyl)tetrazole using time-domain THz spectroscopy and solid-state DFT. A deliberation for the synthesis of nitro/ nitroamino/azido-substituted aryl tetrazole derivatives, such as 2,6-dinitro-4-(1H-tetrazol-1-yl)aniline (C 7 H 5 N 7 O 4 ) (6), N-(2,6-dinitro-4-(1H -tetrazol-1-yl)phenyl)nitramide (C 7 H 4 N 8 O 6 ) (7), 1-(3,4,5-trinitrophenyl)-1H-tetrazole (C 7 H 3 N 7 O 6 ) (8), and 1-(4-azido-3,5-dinitrophenyl)-1H-tetrazole (C 7 H 3 N 9 O 4 ) (9) are recently reported because these compounds exhibit better energetic properties than TNT and are comparable to RDX.…”

Section: ■ Introductionmentioning

confidence: 99%

Time-Domain Terahertz Spectroscopy and Density Functional Theory Studies of Nitro/Nitrogen-Rich Aryl-Tetrazole Derivatives

et al. 2020

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The paper reports the time-domain THz spectroscopy studies of noncentrosymmetric energetic nitro/ nitrogen-rich aryl-tetrazole high-energy molecules. The fingerprint spectra in the THz domain reveal the role of different functional groups attached to position "1" of the tetrazole moiety, which controls the energetic properties. These responses are deliberated through density functional theory (DFT) calculations. The synthesized aryl-tetrazoles exhibit high positive heat of formation (369−744 kJ/mol), high detonation velocities, and pressures (D v : 7734−8298 m·s −1 ; D p : 24−28 GPa) in comparison to the noncentrosymmetric 2,4,6-trinitrotoluene (TNT). These compounds exhibit variation in the refractive indices and absorption between 0.1 and 2.2 THz range. The DFT studies at the molecular and single-crystal level (using plane wave pseudo potential method) endorse in detecting these bands (with ∼1% deviation). The calculated vibrational frequencies and linear optical properties are found to have good agreement with the experimental data in UV−visible and THz regions.

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Using Terahertz Spectroscopy and Solid-State Density Functional Theory to Characterize a New Polymorph of 5-(4-pyridyl)tetrazole

Cited by 17 publications

References 34 publications

Periodic DFT Calculations—Review of Applications in the Pharmaceutical Sciences

Periodic DFT Calculations—Review of Applications in the Pharmaceutical Sciences

Terahertz Time-Domain and Low-Frequency Raman Spectroscopy of Organic Materials

Time-Domain Terahertz Spectroscopy and Density Functional Theory Studies of Nitro/Nitrogen-Rich Aryl-Tetrazole Derivatives

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