Shape of the proton potential in an intramolecular hydrogen-bonded system. Part II

Wojciechowski, Grzegorz; Ratajczak–Sitarz, Małgorzata; Katrusiak, Andrzej; Brzeziński, Bogumił

doi:10.1016/s0022-2860(02)00074-1

Cited by 6 publications

(28 citation statements)

References 23 publications

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“…Recently, we have studied a series of hydrogen-bonded complexes formed between biphenols and 7-methyl-1,5,7triazabicyclo[4.4.0]dec-5-ene (MTBD) hydrogen halogenides (HF, HCl HBr and HI) [1][2][3][4]. It has been demonstrated that MTBD-HX molecules (XZF, Cl, Br or I) form complexes with biphenols, and that the halogenide anions play a very important role in the arrangement of the molecular structure of the complexes.…”

Section: Introductionmentioning

confidence: 99%

Molecular structure of 8-hydroxy-1-methylquinolinium iodide hydrate in crystal and solution

Barczyński¹,

Komasa²,

Ratajczak–Sitarz³

et al. 2006

Journal of Molecular Structure

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8-Hydroxy-1-methylquinolinium iodide monohydrate [(C 10 H 10 NO) C I K $H 2 O] has been studied by X-ray diffraction, FT-IR, 1 H and 13 C NMR spectroscopy. In the crystalline state, the iodide anion is hydrogen-bonded to the water molecule, which in turn is hydrogen bonded to the 8-OH group of the 8-hydroxyquinolinium ring, forming of a symmetric dimer. In acetonitrile and DMSO-d 6 the hydrate assumes a new structure due to almost complete dissociation of the water molecule from the complex structure. In acetonitrile the 8-OH group is hydrogen-bonded to the iodide anion, whereas in DMSO-d 6 it forms the hydrogen bond with the solvent molecules. This 8-OH/O(DMSO-d 6) hydrogen bond is the strongest within the structure of the hydrate.

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Section: Introductionmentioning

confidence: 99%

Molecular structure of 8-hydroxy-1-methylquinolinium iodide hydrate in crystal and solution

Barczyński¹,

Komasa²,

Ratajczak–Sitarz³

et al. 2006

Journal of Molecular Structure

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“…In the current study, we focused on intra- and intermolecular interactions in two N -oxides: 2-(N,N-dimethylamino-N-oxymethyl)-4,6-dimethylphenyl ( 1 ) [ 43 ] and 5,5’-dibromo-3-diethylaminomethyl-2,2’-biphenol N -oxide ( 2 ) [ 44 ]. N -oxides are interesting objects for experimental and theoretical studies because of their unusual chemical structure, possessing N→O bonds, which is involved in inter- or intramolecular hydrogen bond formation [ 45 , 46 , 47 , 48 , 49 ].…”

Section: Introductionmentioning

confidence: 99%

“…The second studied compound denoted as WUKMOE with the CCDC database number: 178615, possesses two intramolecular hydrogen bonds with different strength as reported by Wojciechowski et al [ 44 , 57 ]. The crystal X-ray data indicated a presence of two strong intramolecular hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

“…The second intramolecular hydrogen bond formed between O-H groups was found asymmetrical as it was detected by FT-IR measurements. The molecular conformation of the molecule is non-planar due to a strong overcrowding effect derived from the presence of oxygen atoms involved in the intramolecular hydrogen bonds formation [ 44 ]. The FT-IR experimental measurements in solution and in the solid state are quantitatively comparable [ 44 , 57 ].…”

Section: Introductionmentioning

confidence: 99%

“…The molecular conformation of the molecule is non-planar due to a strong overcrowding effect derived from the presence of oxygen atoms involved in the intramolecular hydrogen bonds formation [ 44 ]. The FT-IR experimental measurements in solution and in the solid state are quantitatively comparable [ 44 , 57 ]. In both solvents, Wojciechowski et al [ 57 ] reported a broad intense absorption in the region 800–1600 cm

.…”

Section: Introductionmentioning

confidence: 99%

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Exploring Intra- and Intermolecular Interactions in Selected N-Oxides—The Role of Hydrogen Bonds

et al. 2022

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Intra- and intermolecular interactions have been explored in selected N-oxide derivatives: 2-(N,N-dimethylamino-N-oxymethyl)-4,6-dimethylphenyl (1) and 5,5’-dibromo-3-diethylaminomethyl-2,2’-biphenol N-oxide (2). Both compounds possess intramolecular hydrogen bonding, which is classified as moderate in 1 and strong in 2, and resonance-assisted in both cases. Density Functional Theory (DFT) in its classical formulation as well as Time-Dependent extension (TD-DFT) were employed to study proton transfer phenomena. The simulations were performed in the gas phase and with implicit and explicit solvation models. The obtained structures of the studied N-oxides were compared with experimental data available. The proton reaction path was investigated using scan with an optimization method, and water molecule reorientation in the monohydrate of 1 was found upon the proton scan progress. It was found that spontaneous proton transfer phenomenon cannot occur in the electronic ground state of the compound 1. An opposite situation was noticed for the compound 2. The changes of nucleophilicity and electrophilicity upon the bridged proton migration were analyzed on the basis of Fukui functions in the case of 1. The interaction energy decomposition of dimers and microsolvation models was investigated using Symmetry-Adapted Perturbation Theory (SAPT). The simulations were performed in both phases to introduce polar environment influence on the interaction energies. The SAPT study showed rather minor role of induction in the formation of homodimers. However, it is worth noticing that the same induction term is responsible for the preference of water molecules’ interaction with N-oxide hydrogen bond acceptor atoms in the microsolvation study. The Natural Bond Orbital (NBO) analysis was performed for the complexes with water to investigate the charge flow upon the polar environment introduction. Finally, the TD-DFT was applied for isolated molecules as well as for microsolvation models showing that the presence of solvent affects excited states, especially when the N-oxide acceptor atom is microsolvated.

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Crystal structure of Schiff base derivative of 2,2′-dihydroxybiphenyl-3-carbaldehyde with n-butylamine

Wojciechowski

Ratajczak–Sitarz

Katrusiak

et al. 2003

Journal of Molecular Structure

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Shape of the proton potential in an intramolecular hydrogen-bonded system. Part II

Cited by 6 publications

References 23 publications

Molecular structure of 8-hydroxy-1-methylquinolinium iodide hydrate in crystal and solution

Molecular structure of 8-hydroxy-1-methylquinolinium iodide hydrate in crystal and solution

Exploring Intra- and Intermolecular Interactions in Selected N-Oxides—The Role of Hydrogen Bonds

Crystal structure of Schiff base derivative of 2,2′-dihydroxybiphenyl-3-carbaldehyde with n-butylamine

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