T. Dziembowska

Wyższa Szkoła Handlowa we Wrocławiu, Vrotslav, Lower Silesian Voivodeship, Poland

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Publications (64)82.54 Total impact

  • Irena Majerz, Teresa Dziembowska
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    ABSTRACT: The influence of substituents and environment on the aromaticity of the naphthalene ring is shown for a series of peri- and para-substituted naphthalenes. Crystal structure geometries are compared with the single molecule structures in vacuum (optimized at the B3LYP/6-311++G** level) and with structures determined in media of different polarity. The HOMA index of the naphthalene rings has been used to characterise the aromaticity of the investigated molecules. It was shown that the ellipticity of the C2-C3 (C6-C7) bonds can be applied as a measure of participation of the quinoid resonance structure and through-resonance effect between the para-substituents.
    The journal of physical chemistry. A. 08/2014;
  • Irena Majerz, Teresa Dziembowska
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    ABSTRACT: For a series of 2,4,6-trinitroanilines substituted with bulky groups, the influence of intramolecular hydrogen bonds, electronic substituents effect, and steric hindrance on aromaticity of the molecules in crystals and their analogues optimized at the B3LYP/6-311++G** level were studied. The HOMA index was used as a measure of the aromaticity, while the parameter ΔP was a description of the distortion of the benzene ring from planarity. Conformation of the nonplanar ring in crystal and optimized structures was also described using the puckering parameters. A comparison of the data for crystal and optimized structures showed an important effect of the intermolecular interactions on aromaticity of the overcrowded nitroanilines. The packing effects were analyzed using the simplified PCM model of solvents. NBO analysis illustrated the changes of orbitals upon dearomatisation.
    The Journal of Physical Chemistry A 05/2012; 116(23):5629-36. · 2.77 Impact Factor
  • Irena Majerz, Teresa Dziembowska
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    ABSTRACT: The influence of intramolecular hydrogen bonds and steric hindrance on distortion from planarity of the benzene ring and its aromaticity is shown for a series of substituted 2,4,6-trinitroanilines. The crystal structure geometry and thegeometry optimized at the B3LYP/6-311++G** level are compared with analogues without intramolecular hydrogen bonds. The HOMA index and the parameter ΔP describing the distortion from planarity of the benzene ring were used to characterize the aromacity of the investigated molecules. NBO and AIM analysis were also applied.
    Annalen der Chemie und Pharmacie 01/2011; 2011(2). · 3.10 Impact Factor
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    ABSTRACT: Thermodynamic parameters of the proton transfer equilibrium for three isomeric N-(ortho-hydrox-ynaphthylmethylene)methylamines have been determined by use of the temperature NMR data and deu-terium isotope effects on 13 C chemical shifts for their solutions in CDCl 3 , CD 3 CN and DMSO-d 6 . The DFT geometry optimization as well as calculation of the energies, dipole moments and HOMA (aromaticity) parameters for the OH and NH tautomers in vacuum and in solution has been performed. Interpretation of origin of the observed differences in the equilibrium constants for the three isomers studied is based on the differences in competition between p-electron delocalization in the quasi-ring involving the intramo-lecular hydrogen bond, differences in the polarity and on the peri interactions.
    Journal of Molecular Structure 07/2010; 979:194-199. · 1.40 Impact Factor
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    ABSTRACT: A series of 15N enriched Schiff bases have been investigated by means of 15N NMR at variable temperature (300-200 K). Most reliable results are obtained below 250 K, as the exchange of the chelate proton is sufficiently slow on the NMR time scale at this temperature. The 15N chemical shifts are found to vary linearly with the one bond 15N-H coupling constants. Deuterium isotope effects on 15N chemical shifts, 1Δ15N(D), show a characteristic S-shape, when plotted vs. the one-bond 15N-H coupling constants. From this graph the intrinsic isotope effects of the two forms can be estimated as 5Δ15N(D)int˜-1.5 ppm and 1Δ15N(D)int˜3 ppm. The intrinsic isotope effects for the OH-form is shown to vary only little for the various substituted compounds investigated. The difference in 15N chemical shifts of the OH-form minus the NH-form is estimated to 100-140 ppm.The dependence of 1Δ15N(D) on the mole fraction is similar to that found for 2ΔC(OD) for other intramolecularly hydrogen bonded cases, β-diketones and Mannich bases and looks very similar to that determined for 1Δ15N(D) of the organic acid-pyridine complex.
    Berichte der Bunsengesellschaft für physikalische Chemie. 06/2010; 102(3):410 - 413.
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    ABSTRACT: The structure of two ortho-hydroxy N-methyl Schiff bases as well as the selfcondensation product of 2-(N-methyliminomethyl)-phenol are determined by X-Ray crystallography and by ab initio DFT, on B3LYP/6-31G** level, calculations. Electronic coupling between acidic and basic centres of the molecules, especially effective in the proton transfer structure, is discussed on the basis of detailed analysis of differentiation of bond lengths both in aromatic and chelate rings. Consequences of this coupling on the intramolecular hydrogen bonding and proton transfer process are discussed.
    Berichte der Bunsengesellschaft für physikalische Chemie. 06/2010; 102(3):393 - 402.
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    ABSTRACT: The spectra of the real and imaginary components of the complex refractive index were determined in the NIR and MIR regions for liquid Benzylidenemethylamine and intramolecularly hydrogen-bonded o-Hydroxybenzylidenemethylamine from transmission studies using a method, which takes into account the dispersion of the refractive index in the Visible range and requires integration over the entire NIR and MIR region.From these data the spectra of both components of the complex electric permittivity and complex polarizability of both liquids were determined in the Visible, Near Infrared, and Mid Infrared spectral regions (25,000–600cm−1). The molar vibrational polarization related to various spectral ranges has been determined. The considerable contribution due to the formed intramolecular H-bonding has been evaluated and discussed.
    Journal of Molecular Structure 01/2010; 976(1):243-248. · 1.40 Impact Factor
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    ABSTRACT: The structure of the Schiff base derived from 2-hydroxy-1-naphthaldehyde and methylamine (1) has been studied by X-ray diffraction, B3LYP/6-31G(d,p) calculations, NMR and FTIR spectroscopy. The crystal is monoclinic, space group P21/c, with symmetry-independent two molecules forming a dimer (1) via two short intramolecular (2.592(2) and 2.579(2) Å) and two longer intermolecular (2.957(2) and 3.053(2) Å) N–H···O hydrogen bonds. The structures of dimer (2) and two monomers (3 and 4) have been analyzed by B3LYP/6-31G(d,p) level of theory. Tautomeric equilibrium due to the intramolecular hydrogen transfer between enol and ketol forms (4⇌3) has been studied in five solvents on the basis of 13C NMR chemical shifts and equilibrium constants, Keq, determined. The equilibrium constants, Keq, have been found to increase linearly with the solvent parameter, ET. Linear correlations have also been established between the experimental 1H and 13C NMR chemical shifts (δexp) of keto (3) and enol (4) units in five solvents and the GIAO/B3LYP/6-31G(d,p) calculated magnetic isotropic shielding tensors (σcalc) using COSMO screening solvation model, δexp = a + bσcalc.
    Journal of Molecular Structure 07/2009; 929:32-42. · 1.40 Impact Factor
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    ABSTRACT: Intramolecular hydrogen bonding in the primarily and secondarily substituted quinoline-2-carboxamides and their N-oxides has been studied in the solution by multinuclear NMR spectroscopy. Hydrogen bonding patterns and supramolecular arrangement in the solid state have been determined by single crystal X-ray analysis. In quinoline-2-carboxamides weak, nonlinear intramolecular N−H...N hydrogen bond is present, but in the solid state the intermolecular hydrogen bonds and packing forces are the factors that decide on the properties of 3D structures. In quinoline-2-carboxamide N-oxides the most important structural features are the intramolecular hydrogen bonds. Details of different weak interactions and resulting 3D arrangement of molecules are discussed. In the solution, two separate 1H signals are observed for the primary quinoline-2-carboxamides in the range from ca. 5.8 to 8.1 ppm. The chemical shifts of the NH group’s proton for studied R'-quinoline-2-R-carboxamides are in the range from 8.1 to 8.4 ppm. For the N-oxide of 4-R'-quinoline-2-carboxamides (R' = H, Me, OPh, Cl and Br), the values of the proton chemical shifts of the NH group in the range from 10.78 to 11.38ppm (for primary amides) indicating that this group forms hydrogen bonds with the oxygen of the N-oxide group. This bond is stronger than the N−H...N bond in quinoline-2-carboxamides. For the secondary amide N-oxides, the δ(NH) values are increasing from 11.25 to 11.77ppm in the sequence of substituents 4-Br < 4-Cl < 4-H < 4-Me < 4-OPh. For 4-substituted compounds these values depend also on the substituent effect.
    Journal of Physical Organic Chemistry 01/2009; 22:857-871. · 1.58 Impact Factor
  • P. E. Hansen, Z. Rozwadowski, T. Dziembowska
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 01/2009; 40(27).
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    ABSTRACT: Tautomeric forms of N-(5-nitrosalicylidene)-2-butylamine in various solvents were studied with the IR and NMR (1H, 13C) spectroscopy. Also computational studies of keto-amine (O···HN) and enol-imine (OH···N) tautomers of N-(5-nitrosalicylidene)-2-butylamine molecule in the ground state were carried out with the DFT and SCRF theory at B3LYP/6-31G(d,p) level. Experimental data show that the solvent can invert the keto-amino: enol-imine equilibrium. The enol-imine tautomer prevails in non polar CCl4 and weakly polar CDCl3 or CD2Cl2 solvents, while in polar CD3CN solvent the keto-amine form dominates. Theoretical results agree qualitatively with the experimental findings and suggest also that predominance of particular tautomers can be influenced by the aliphatic chain geometry. Theoretical enol-imine model structure corresponding to the vacuum or non polar environment e.g.CCl4 is more stable than the keto-amino counterpart. On the contrary, the keto-amino form is predicted to be more stable than the enol-imine form in aqueous or in CH3CN polar environments. A satisfactory correlation between theoretical 1H and 13C shielding constants and experimental 1H and 13C chemical shifts becomes an additional argument that the three-dimension structures predicted theoretically should appear in the experimental conditions.
    Journal of Molecular Structure 01/2009; 928(1):25-31. · 1.40 Impact Factor
  • Irena Majerz, T. Dziembowska
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    ABSTRACT: The structure and vibrational spectra of the tautomeric NH form of trans-N,N′-bis-(R-salicylidene)-cyclohexanediamines (R = H, 5-NO2, 4,6-OCH3, 3,5-Cl) and their analogues deuterated in the NH and CH imine groups were calculated using the DFT method at the 6-31G** level. The complicated nature of the normal modes was shown. The influence of the substituents on the hydrogen bond strength and nonequivalence of the two hydrogen bonds present in Schiff base molecules are discussed.
    Spectroscopy Letters 01/2009; 42(5):246-257. · 0.67 Impact Factor
  • P. E. Hansen, Z. Rozwadowski, T. Dziembowska
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    ABSTRACT: The review covers the use of chemical shifts, isotope effects on chemical shifts and coupling constants in the description of Schiff bases. o-Hydroxy Schiff bases are often tautomeric and special attention is devoted to this feature. Nuclei in question are 1H, 13C, 15N, 19F and 17O. As well primary as secondary isotope effects are treated. Deuterium isotope effects on 13C and 15N chemical shifts are treated in detail and the theoretical background is dealt with. Finally, various applications of Schiff bases in biology and stereochemistry are discussed.
    Current Organic Chemistry 12/2008; 13(2):194-215. · 3.04 Impact Factor
  • Irena Majerz, Teresa Dziembowska
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    ABSTRACT: The presence of intramolecular NHN hydrogen bond in 4-R-quinoline-2-(N-R′-carboxamides) was investigated by AIM methodology. Values of electron density, elipticity, and total energy density at the bond critical point of H···N in amides were compared with respective values of H···O in their N-oxides. Copyright © 2008 John Wiley & Sons, Ltd.
    Journal of Physical Organic Chemistry 06/2008; 21(10):876 - 880. · 1.58 Impact Factor
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    ABSTRACT: The structure of some glucosamine Schiff bases has been studied by means of ab initio RHF and DFT calculation and CP/MAS 13C and 15N NMR measurements. The anomeric and tautomeric equilibria in a DMSO solution have been studied by 1H, 13C and 15N NMR spectroscopy. The anomeric composition of d-2-glucosamine Schiff bases in the solid state and in DMSO solution has been shown to depends on the tautomeric form of Schiff bases and electronic properties of substituents on the aromatic ring.
    Journal of Molecular Structure 11/2007; 844:32-37. · 1.40 Impact Factor
  • I. Majerz, T. Dziembowska, K. Ambroziak
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    ABSTRACT: Vibrational spectra of trans-N,N′-bis-(R-salicylidene)-cyclohexanediamine (R=H, 5-NO2, 4,6-OCH3, 3,5-Cl) and its analogues deuterated in OH and imine CH groups were calculated using DFT method at 6-31G** level. The presence of strong coupling in the molecules was evidenced.
    Journal of Molecular Structure - J MOL STRUCT. 01/2007; 828(1):166-173.
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    ABSTRACT: The two structurally related Schiff bases, 2-hydroxynaphthylidene-(8-aminoquinoline) (HNAQ) and 2-hydroxynaphthylidene-1(')-naphthylamine (HNAN), were studied by means of steady-state and time resolved optical spectroscopies as well as time-dependent density functional theory (TDDFT) calculations. The first one, HNAQ, is stable as a keto tautomer in the ground state and in the excited state in solutions, therefore it was used as a model of a keto tautomer of HNAN which exists mainly in its enol form in the ground state at room temperature. Excited state intramolecular proton transfer in the HNAN molecule leads to a very weak (quantum yield of the order of 10(-4)) strongly Stokes-shifted fluorescence. The characteristic time of the proton transfer (about 30 fs) was estimated from femtosecond transient absorption data supported by global analysis and deconvolution techniques. Approximately 35% of excited molecules create a photochromic form whose lifetime was beyond the time window of the experiment (2 ns). The remaining ones reach the relaxed S(1) state (of a lifetime of approximately 4 ps), whose emission is present in the decay associated difference spectra. Some evidence for the back proton transfer from the ground state of the keto form with the characteristic time of approximately 13 ps was also found. The energies and orbital characteristics of main electronic transitions in both molecules calculated by TDDFT method are also discussed.
    The Journal of Chemical Physics 12/2006; 125(18):184508. · 3.12 Impact Factor
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    ABSTRACT: Femtosecond time-resolved absorption spectra of two structurally related, internally H-bonded Schiff bases are reported. The 2-hydroxynaphthylidene-1′-naphthylamine (HNAN) stable as an enol tautomer undergoes an ultrafast excited state intramolecular proton transfer, while the 2-hydroxynaphthylidene-(8′-aminoquinoline) (HNAQ), stable as a keto structure, reveals unusual relaxation routes after electronic excitation. In particular, the rise of the bleaching band with the characteristic time of ∼700fs was found and attributed to a gradual population of the S1 fluorescent state from a ‘hot’ excited state. The results accompanied by TDDFT calculations are used to construct the diagram of relaxation routes of an excited HNAQ molecule.
    Chemical Physics Letters 12/2005; 416(4):305-310. · 2.15 Impact Factor
  • T. Dziembowska, P. E. Hansen, Z. Rozwadowski
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    ABSTRACT: For Abstract see ChemInform Abstract in Full Text.
    ChemInform 01/2005; 36(3).
  • T. Dziembowska, K. Ambroziak, I. Majerz
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    ABSTRACT: The vibrational spectra of two tautomeric forms of trans-N,N′-bis-salicylidene cyclohexanediamine (OHN-sal and NHO-sal) as well as the reference compound with weak hydrogen bond (OH-sal) have been analysed using DFT and HF methods. The results have revealed the most important spectroscopic consequences of formation of the medium strength intramolecular OH⋯N hydrogen bond and the proton transfer in Schiff bases. The IR spectrum of OHN-sal calculated by the B3LYP/6-31G(d,p) method is in a satisfactory agreement with the experimental one. The discrepancies result from the neglect of the anharmonicity correction and intermolecular interactions. The HF/6-31G level of theory do not reproduce correctly the intramolecular hydrogen bond in the Schiff base studied.
    Journal of Molecular Structure 01/2005; 738(1):15-24. · 1.40 Impact Factor

Publication Stats

308 Citations
82.54 Total Impact Points

Institutions

  • 2012
    • Wyższa Szkoła Handlowa we Wrocławiu
      Vrotslav, Lower Silesian Voivodeship, Poland
  • 2009–2012
    • West Pomeranian University of Technology, Szczecin
      • Institute of Chemical and Environmental Engineering
      Stettin, West Pomeranian Voivodeship, Poland
    • Roskilde University
      • Department of Science, Systems and Models (NSM)
      Roskilde, Zealand, Denmark
  • 1996–2010
    • Szczecin University of Technology
      • Institute of Chemistry and Environmental Protection
      Stettin, West Pomeranian Voivodeship, Poland
  • 2000
    • University of Wroclaw
      • Faculty of Chemistry
      Wrocław, Lower Silesian Voivodeship, Poland