Crystal structure and Hirshfeld surface analysis of the hydrated 2:1 adduct of piperazine-1,4-diium 3,5-dinitro-2-oxidobenzoate and piperazine

Subha, V. S.; Seethalakshmi, T.; Balakrishnan, T.; Percino, M. Judith; Venkatesan, Perumal

doi:10.1107/s2056989022000226

Cited by 4 publications

(1 citation statement)

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“…The presence of hydrogen bonds between proton donors and acceptors plays an important role with respect to the formation and stability of 1:1 or 2:1 proton-transfer salts (Smith & Wermuth, 2010a,b, 2011, 2013c, 2014Smith et al, 2007Smith et al, , 2008Subha et al, 2022). Various organic bases can receive a proton and become protonated cations, examples being pyrazine (Lengyel et al, 2019), piperazine (Ding et al, 2014;Muslim et al, 2021;Subha et al, 2022), imidazole (Massey et al, 2016;Khan et al, 2021), indole (Ma et al, 2018), quinoline (Belombe et al, 2011;Li et al, 2012;Khan et al, 2022), 1,2,4-triazole and other azoles (Luo et al, 2011;Massey et al, 2012;Tucker et al, 2015;Singh et al, 2021), hydrazine (Smith et al, 2009), benzamidine (Portalone, 2010(Portalone, , 2014Irrera et al, 2012), sulfamethazine (Padrela et al, 2019), guanidine (Smith et al, 2007;Ghasemi et al, 2019), adenine (Sedghiniya et al, 2019) and amines (Rosokha et al, 2006;Zhang & Zhu, 2007;Ding et al, 2012Ding et al, , 2013Smith & Wermuth, 2013a, 2016Shmukler et al, 2019;El-Dissouky et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

Proton-transfer salts of diphenylphosphinic acid with substituted 2-aminopyridine: crystal structure, spectroscopic and DFT studies

Yuan

Zhang

et al. 2023

Acta Crystallogr C

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Three proton-transfer salts of diphenylphosphinic acid (DPPA) with 2-amino-5-(X)-pyridine (AMPY, X = Cl, CN or CH3), namely, 2-amino-5-chloropyridinium diphenylphosphinate, C5H6ClN2 +·C12H10O2P− (1, X = Cl), 2-amino-5-cyanopyridinium diphenylphosphinate, C6H6N3 +·C12H10O2P− (2, X = CN), and 2-amino-5-methylpyridinium diphenylphosphinate, C6H9N2 +·C12H10O2P− (3, X = CH3), have been synthesized and characterized by FT–IR and 1H NMR spectroscopy, and X-ray crystallography. The crystal structures of compounds 1–3 were determined in the space group P\overline{1} for 1 and 2, and C2/c for 3. All three compounds contain N—H...O hydrogen-bonding interactions due to proton transfer from the O=P—OH group of DPPA as donor to the pyridine N atom of AMPY as acceptor. The proton transfer of compounds 1–3 was also verified by 1H NMR and FT–IR spectroscopy. The stoichiometry of all three proton-transfer salts was determined to be 1:1 and the Benesi–Hildebrand equation was applied to determine the formation constant (K CT) and the molar extinction coefficient (ɛCT) in each case. Theoretical density functional theory (DFT) calculations were performed to investigate the optimized geometries, the molecular electrostatic potentials (MEP) and the highest occupied molecular orbitals (HOMO) and lowest unoccupied molecular orbitals (LUMO) of all three proton-transfer salts. The results showed good agreement between the experimental data and the DFT computational analysis.

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