European Journal of Chemistry

4-Carboxyanilinium dihydrogen phosphate monohydrate, an organophosphate adducts of 4-amino benzoic acid: Structural, vibrational, thermal, and computational studies

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Published: Mar 31, 2024
DOI: https://doi.org/10.5155/eurjchem.15.1.1-16.2484
Keywords:
DSC, FTIR, X-ray diffraction, Single crystal structure, 4-Carboxyanilinium dihydrogen phosphate monohydrate
Section
Research Article
Issue
Vol. 15 No. 1 (2024): March 2024
Dates
Received 2023-10-22
Accepted 2023-12-26
Published 2024-03-31
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Lata Panicker
Protein Crystallography Section, Bioscience Group, Bhabha Atomic Research Center, Trombay, Mumbai 400085, India
https://orcid.org/0000-0001-5448-7502

Abstract

4-Carboxyanilinium dihydrogen phosphate monohydrate (4-CAH2PO4·H2O), an organophosphate adduct, was synthesized and characterized by single-crystal X-ray diffraction, Fourier transform infrared (FTIR), Differential scanning calorimetry (DSC) and computational analysis performed using CrystalExplorer 21, Gaussian 09W and Multiwfn 3.7 software. The complex 4-CAH2PO4·H2O crystallized in the triclinic space group, P-1, with two molecules each of 4-carboxyanilinium (4-CA) cations, H2PO4– anions, and water, respectively, in an asymmetric unit. Crystal data for C7H12NO7P: triclinic, space group P-1, a = 8.5238(2) Å, b = 8.9068(2) Å, c = 14.4976(4) Å, α = 106.456(2)°, β = 90.195(2)°, γ = 92.811(2)°, V = 1054.13(5) Å3, Z = 4, T = 293 K, μ(Cu Kα) = 2.587 mm-1, Dcalc = 1.595 g/cm3, 18182 reflections measured (6.358° ≤ 2Θ ≤ 146.396°), 4149 unique (Rint = 0.1018, Rsigma = 0.0521) which were used in all calculations. The final R1 was 0.0584 (I > 2σ(I)) and wR2 was 0.1712 (all data). The organic layer containing 4-CA cations and the inorganic layer containing phosphate anions and water molecules in 4-CAH2PO4·H2O crystals are connected through a three-dimensional network of strong charge-assisted N–H···O and C-OH···O hydrogen bonds. The fingerprint plot of 4-CAH2PO4·H2O obtained indicated that the most prominent interaction corresponds to the short O···H contact, followed by the H···H and H···C contacts. The intermolecular interaction topology of 4-CAH2PO4·H2O has been quantitatively analyzed. The 4-CAH2PO4·H2O complex was optimized by density functional theory (DFT) with B3LYP/6-31G basis set and the theoretical IR vibrational spectra determined. The noncovalent interaction (NCI) and quantum theory of the atom in the molecule (QTAIM) analysis were done using Multiwfn 3.7 software. 4-CAH2PO4·H2O complex structure and its computational analysis are also compared with that of 4-carboxyanilinium dihydrogen phosphate (4-CAH2PO4).


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Panicker, L. 4-Carboxyanilinium Dihydrogen Phosphate Monohydrate, an Organophosphate Adducts of 4-Amino Benzoic Acid: Structural, Vibrational, Thermal, and Computational Studies. Eur. J. Chem. 2024, 15, 1-16.

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The Heavy Water Board, Bhabha Atomic Research Center, Trombay, Mumbai 400085, India
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