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Title: Structural, spectroscopic and theoretical studies of dimethylphenyl betaine complex with two molecules of 2,6-dichloro-4-nitro-phenol
Authors: Szafran, Mirosław
Komasa, Anna
Ostrowska, Kinga
Katrusiak, Andrzej
Dega-Szafran, Zofia
Keywords: Dimethylphenyl betaine
Hydrogen bonds
X-ray diffraction
FTIR and NMR spectra
B3LYP calculations
Issue Date: 5-Feb-2015
Citation: SPECTROCHIMICA ACTA 136 A (2015) 1216-1226
Abstract: The 1:2 complex (1) of dimethylphenyl betaine (DMPB) with two molecules of 2,6-dichloro-4-nitro-phenol (DCNP) was prepared and characterized by X-ray diffraction, B3LYP/6-311++G(d,p) and B3LYP-D3/6-311++G(d,p)calculations, FTIR and NMR spectroscopies. The crystal is monoclinic, space group P2(1)/c with Z = 4. The protons at the oxygen atoms of phenols are bonded to each oxygen atoms of the DMPB carboxylate group by two nonequivalent H-bonds with the O-H center dot center dot center dot O distances of 2.473(5) and 2.688(4) angstrom. Both H-bonds in the optimized structures 2 (in vacuum), 3 (in DMSO solution) and dispersion-correlated functional (D3) 4 (in vacuum) are comparable and are slightly shorter than O(6)-H(O6)center dot center dot center dot O(2) in the crystal. The FOR spectrum of 1 shows a broad absorption in the 3400-2000 cm(-1) region corresponding to a longer hydrogen bond and a broad absorption in the 1800-500 cm(-1) region caused by the shorter H-bond. The relations between the experimental C-13 and H-1 chemical shifts (delta(exp)) of the investigated compound 1 in DMSO solution and GIAO/B3LYP/6-311++G(d,p) magnetic isotropic shielding constants (sigma(calc)) obtained by using the screening solvation model (COSMO) for 3 are linear and reproduce well the experimental chemical shifts described by the equation: delta(exp) = a + b sigma(calc).
ISSN: 1386-1425
Appears in Collections:Artykuły naukowe (WCh)

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