Synthesis, Molecular Structure of Diethyl Phenylenebis(Methylene)Dicarbamates and FTIR Spectroscopy Molecular Recognition Study with Benzenediols

Saucedo-Balderas, Marlene M.; Delgado-Alfaro, Rogelio A.; Martínez‐Martínez, Francisco J.; Ortegón-Reyna, David; Bernabé-Pineda, Margarita; Zúñiga-Lemus, Oscar; González-González, Juan Saulo

doi:10.5935/0103-5053.20140289

Cited by 4 publications

(3 citation statements)

References 4 publications

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“…Meanwhile, the band in the 3300 cm −1 range shifted to higher frequencies with ∆(νO-H) = 105 cm −1 . This shift is in agreement with previous reports about molecular complexes formed by O-H•••O=C hydrogen bond interactions between catechol with oxalamates and carbamates [24,25]. The carbonyl C=O stretching bands of TEO (Figure 2) were shifted in the IR spectrum of the CAT-TEO ground mixture as a consequence of the formation of the cocrystal (Table 1), with absolute values of ∆(νC=O) less than 20 cm −1 .…”

Section: Ir Spectroscopysupporting

confidence: 92%

“…Meanwhile, the band in the 3300 cm −1 range shifted to higher frequencies with Δ(νO-H) = 105 cm −1 . This shift is in agreement with previous reports about molecular complexes formed by O-H•••O=C hydrogen bond interactions between catechol with oxalamates and carbamates [24,25]. In the IR spectrum of CAT-TEO obtained after 15 min of grinding (Figure 2), the O-H stretching bands (Table 1) were shifted with respect to the starting products and the physical mixture (CAT-TEO-MIX, Figure 2).…”

Section: Ir Spectroscopysupporting

confidence: 91%

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Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure

González-González¹,

Jiménez-López²,

Ortegón-Reyna³

et al. 2021

Applied Sciences

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Pharmaceutical cocrystallization offers the possibility to modify the physicochemical and biopharmaceutical properties of active pharmaceutical ingredients. The mechanochemical synthesis and spectroscopic characterization of the catechol-theophylline (CAT-TEO) cocrystal is reported. The cocrystal was prepared by the solvent-assisted grinding method. The ATR-IR spectroscopy study allowed to determine the formation of the cocrystal because the O-H and C=O stretching bands in the CAT-TEO cocrystal were shifted with respect to the starting materials, suggesting the formation of the C=O···H-O hydrogen bond interaction. Infrared spectroscopy also allowed to discard hydration of the cocrystal, and polymorphic transitions of the starting products as a consequence of the mechanochemical grinding. The X-ray powder diffraction and thermal studies confirmed the formation of a new solid phase. In the solid state 13C NMR spectra of the cocrystal, the signals were shifted with respect to the starting products. The 13C NMR chemical shifts of the CAT-TEO cocrystal were simulated by using the gauge including the atomic orbital (GIAO) method. These results showed a good correlation between the experimental and calculated 13C NMR results. Theoretical calculations and natural bonding orbital analysis (NBO) at a B3LYP/6-31G(d,p) level of theory were performed to obtain structural information of the cocrystal.

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Section: Ir Spectroscopysupporting

confidence: 92%

Section: Ir Spectroscopysupporting

confidence: 91%

Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure

González-González¹,

Jiménez-López²,

Ortegón-Reyna³

et al. 2021

Applied Sciences

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“…The O-H stretching frequency was shifted (Table 2) with ΔνO-H = −28 cm −1 , +207 cm −1 and +290 cm −1 ; meanwhile, the C=O frequency was shifted with a ΔνC=O of −28 cm −1 . These shifts are a consequence of the rearrangement of the hydrogen bond patterns with respect to the noncomplexed forms, and are in agreement with previous reports about lidocaine complexes, and dihydroxybenzenes with phenylenebis(methylene)dicarbamates and phenyldioxalamates [7,8,27,28]. The N-H stretching frequency showed a small shift (ΔνN-H = −2 cm −1 , which is out of the spectral resolution), suggesting that the N-H group is not involved in the formation of the complex.…”

Section: Infrared Spectroscopysupporting

confidence: 92%

Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex

Magaña-Vergara

Cruz-Cruz²,

Peraza-Campos

et al. 2018

Crystals

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Molecular complexation is a strategy used to modify the physicochemical or biopharmaceutical properties of an active pharmaceutical ingredient. Solvent assisted grinding is a common method used to obtain solid complexes in the form of cocrystals. Lidocaine is a drug used as an anesthetic and for the treatment of chronic pain, which bears in its chemical structure an amide functional group able to form hydrogen bonds. Polyphenols are used as cocrystal coformers due to their ability to form O-H···X (X = O, N) hydrogen bond interactions. The objective of this study was to exploit the ability of phloroglucinol to form molecular complexes with lidocaine by liquid assisted grinding. The formation of the complex was confirmed by the shift of the O-H and C=O stretching bands in the IR spectra of the polycrystalline ground powders, suggesting the formation of O-H···O=C hydrogen bonds. Hydration of the complexes also was confirmed by IR spectroscopy and by powder X-ray diffraction. The molecular structure was determined by single crystal X-ray diffraction.

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Exploring the nutrient capture efficiency of activated biochar

Rajeshwer,

John

2024

AIP Conference Proceedings

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Synthesis, Molecular Structure of Diethyl Phenylenebis(Methylene)Dicarbamates and FTIR Spectroscopy Molecular Recognition Study with Benzenediols

Cited by 4 publications

References 4 publications

Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure

Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure

Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex

Exploring the nutrient capture efficiency of activated biochar

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