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Dr. Robert Dobosz
Institute of Mathematics and Physics, UTP University of Science and Technology, Bydgoszcz, Poland

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0 proton transfer
0 inter- and intramolecular interactions
0 aromaticity
0 interaction between amino-acids

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DFT calculations

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Journal article
Published: 05 October 2020 in Energies
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The article presents applications of systems with power electronic converters, high voltage transformers, and discharge chambers used for nonthermal, dielectric barrier discharge plasma treatment of a plastic surface and decontamination of organic loose products. In these installations, the inductance of the high voltage transformers and the capacitances of the electrode sets form resonant circuits that are excited by inverters. The article presents characteristic features of the installations and basic mathematical relationships as well as the impact of individual parameters of system components. These converters with their output installations were designed, built, and tested by the authors. Some of the converters developed by the authors are manufactured and used in the industry.

ACS Style

Jan Mucko; Robert Dobosz; Ryszard Strzelecki. Dielectric Barrier Discharge Systems with HV Generators and Discharge Chambers for Surface Treatment and Decontamination of Organic Products. Energies 2020, 13, 5181 .

AMA Style

Jan Mucko, Robert Dobosz, Ryszard Strzelecki. Dielectric Barrier Discharge Systems with HV Generators and Discharge Chambers for Surface Treatment and Decontamination of Organic Products. Energies. 2020; 13 (19):5181.

Chicago/Turabian Style

Jan Mucko; Robert Dobosz; Ryszard Strzelecki. 2020. "Dielectric Barrier Discharge Systems with HV Generators and Discharge Chambers for Surface Treatment and Decontamination of Organic Products." Energies 13, no. 19: 5181.

Journal article
Published: 01 January 2020 in Energies
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Gibbs free energies, based on DFT (Density Functional Theory) calculations, prove that enaminone (2-(anilinemethylidene)cyclohexane-1,3-dione) and ketamine (2-[(phenylimino)-methyl]cyclohexane-1,3-dione) are the most and least stable tautomeric forms of the studied systems, respectively. 1H and 13C NMR spectra prove that 2-(anilinemethylidene)cyclohexane-1,3-diones are the only tautomeric species present in dimethylsulfoxide solution (a very weak signal can be seen only for the p-methoxy derivatives). The zwitterionic character of these enaminones is strengthened by naphthoannulation and by the insertion of the electron-withdrawing substituent into the benzene ring (the latter weakens the intramolecular hydrogen bond in the compound). Substituent and naphtoannulation have no effect on the stability of the studied tautomers. Slight twisting of the benzene ring, with respect to the CArNC plane (seen in the crystalline state), was proven to also take place in vacuum and in solution.

ACS Style

Robert Dobosz; Jan Mućko; Ryszard Gawinecki. Using Chou’s 5-Step Rule to Evaluate the Stability of Tautomers: Susceptibility of 2-[(Phenylimino)-methyl]-cyclohexane-1,3-diones to Tautomerization Based on the Calculated Gibbs Free Energies. Energies 2020, 13, 183 .

AMA Style

Robert Dobosz, Jan Mućko, Ryszard Gawinecki. Using Chou’s 5-Step Rule to Evaluate the Stability of Tautomers: Susceptibility of 2-[(Phenylimino)-methyl]-cyclohexane-1,3-diones to Tautomerization Based on the Calculated Gibbs Free Energies. Energies. 2020; 13 (1):183.

Chicago/Turabian Style

Robert Dobosz; Jan Mućko; Ryszard Gawinecki. 2020. "Using Chou’s 5-Step Rule to Evaluate the Stability of Tautomers: Susceptibility of 2-[(Phenylimino)-methyl]-cyclohexane-1,3-diones to Tautomerization Based on the Calculated Gibbs Free Energies." Energies 13, no. 1: 183.

Preprint
Published: 27 November 2019
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In this paper we review dynamics and roughness of bonds in proteins on example of albumin, that is important from the physiological point of view. We have performed computer simulations of albumin chain. Statistics were collected by performing many simulations realizations for each experimental setting. We concentrate on hydrogen bonds, cation-π and π- π interactions and NP contacts. Histograms of hydrogen bonds length are positively skewed in contrary to histograms of interactions and HP contacts that are negatively skewed. Scaling exponents of power spectra of energies of bonds / interactions /contacts are in range -0.2 to -0.5 and significantly differ between various hydrogen bonds or interactions. Varying scaling of such spectra can be used to classify between distinct bonds or contacts. Concerning particular amino-acids, largest amount of HBO H20 bonds are between Glutamate (GLU) amino-acids and water particle, while large amount of HBO bonds are formed with Lysine (LYS). For HP contacts the mayor role plays Phenylalanine (PHE) and Leucine (LEU) amino-acids. From decay curves HBO H2O bonds decays in fastest rate, while HBO bonds and HP contacts at slowest rate. We present as well decay curves of bonds formed by particular amino-acids, that gives interesting results.

ACS Style

Krzysztof Domino; Damian Bełdowski; Adam Mazurkiewicz; Janusz Musiał; Małgorzata Słomion; Robert Dobosz. Analysis of Protein Intramolecular and Solvent Bonding on Example of Major Synovial Fluid Component. 2019, 1 .

AMA Style

Krzysztof Domino, Damian Bełdowski, Adam Mazurkiewicz, Janusz Musiał, Małgorzata Słomion, Robert Dobosz. Analysis of Protein Intramolecular and Solvent Bonding on Example of Major Synovial Fluid Component. . 2019; ():1.

Chicago/Turabian Style

Krzysztof Domino; Damian Bełdowski; Adam Mazurkiewicz; Janusz Musiał; Małgorzata Słomion; Robert Dobosz. 2019. "Analysis of Protein Intramolecular and Solvent Bonding on Example of Major Synovial Fluid Component." , no. : 1.

Article
Published: 26 June 2017 in Journal of Polymer Science Part A: Polymer Chemistry
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A few N-alkoxypyridinium salts are developed as photoinitiators for efficient polymerization reactions. They are characterized by absorption properties below 300 nm, and generate alkoxy radicals on UV-Vis light exposure. The squarylium dye was used as a blue-light photosensitizer. Polymerization results are correlated with the photochemistry of N-alkoxypyridinium salts. The quenching of the excited singlet state of squarylium dye by pyridinium salt and the formation of the semioxidized species of squaraine suggests an electron transfer from an excited dye to a coinitiator, and that the resulting oxygen-centered radical initiates the polymerization process. The chemical mechanism was investigated by steady state photolysis and nanosecond laser flash photolysis experiments. Photoinitiating activity of new photoinitiators for initiation of polymerization of trimethylolpropane triacrylate in the UV-blue light region was compared with photoinitiating ability of selected commercially available initiators. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2840–2850

ACS Style

Janina Kabatc; Katarzyna Kostrzewska; Robert Dobosz; Łukasz Orzeł; Katarzyna Jurek. N -alkoxypyridinium salts as coinitiators in radical polymerization: Synthesis and Photochemical Properties. Journal of Polymer Science Part A: Polymer Chemistry 2017, 55, 2840 -2850.

AMA Style

Janina Kabatc, Katarzyna Kostrzewska, Robert Dobosz, Łukasz Orzeł, Katarzyna Jurek. N -alkoxypyridinium salts as coinitiators in radical polymerization: Synthesis and Photochemical Properties. Journal of Polymer Science Part A: Polymer Chemistry. 2017; 55 (17):2840-2850.

Chicago/Turabian Style

Janina Kabatc; Katarzyna Kostrzewska; Robert Dobosz; Łukasz Orzeł; Katarzyna Jurek. 2017. "N -alkoxypyridinium salts as coinitiators in radical polymerization: Synthesis and Photochemical Properties." Journal of Polymer Science Part A: Polymer Chemistry 55, no. 17: 2840-2850.

Journals
Published: 02 May 2017 in Polymer Chemistry
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2-Ethyl-2-(hydroxymethyl)-1,3-propanediol triacrylate was polymerized in the presence of squarylium dye and various onium salts.

ACS Style

Katarzyna Kostrzewska; Joanna Ortyl; Robert Dobosz; Janina Kabatc. Squarylium dye and onium salts as highly sensitive photoradical generators for blue light. Polymer Chemistry 2017, 8, 3464 -3474.

AMA Style

Katarzyna Kostrzewska, Joanna Ortyl, Robert Dobosz, Janina Kabatc. Squarylium dye and onium salts as highly sensitive photoradical generators for blue light. Polymer Chemistry. 2017; 8 (22):3464-3474.

Chicago/Turabian Style

Katarzyna Kostrzewska; Joanna Ortyl; Robert Dobosz; Janina Kabatc. 2017. "Squarylium dye and onium salts as highly sensitive photoradical generators for blue light." Polymer Chemistry 8, no. 22: 3464-3474.

Journal article
Published: 01 April 2016 in Dyes and Pigments
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ACS Style

Janina Kabatc; Katarzyna Kostrzewska; Katarzyna Jurek; Robert Dobosz; Łukasz Orzeł. 1,3-Bis(phenylamino)squaraine – Photophysical and photochemical properties. Dyes and Pigments 2016, 127, 179 -186.

AMA Style

Janina Kabatc, Katarzyna Kostrzewska, Katarzyna Jurek, Robert Dobosz, Łukasz Orzeł. 1,3-Bis(phenylamino)squaraine – Photophysical and photochemical properties. Dyes and Pigments. 2016; 127 ():179-186.

Chicago/Turabian Style

Janina Kabatc; Katarzyna Kostrzewska; Katarzyna Jurek; Robert Dobosz; Łukasz Orzeł. 2016. "1,3-Bis(phenylamino)squaraine – Photophysical and photochemical properties." Dyes and Pigments 127, no. : 179-186.

Journal article
Published: 01 April 2015 in Journal of Molecular Liquids
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ACS Style

Robert Dobosz; Janina Kabatc. Corrigendum to “The N-(2-carboxyethyl)hemicyanine dyes. Synthesis, spectroscopic and quantum-chemical studies” [J. Mol. Liq. 202 (2015) 141–147, doi:10.1016/j.molliq.2014.12.019]. Journal of Molecular Liquids 2015, 204, 270 .

AMA Style

Robert Dobosz, Janina Kabatc. Corrigendum to “The N-(2-carboxyethyl)hemicyanine dyes. Synthesis, spectroscopic and quantum-chemical studies” [J. Mol. Liq. 202 (2015) 141–147, doi:10.1016/j.molliq.2014.12.019]. Journal of Molecular Liquids. 2015; 204 ():270.

Chicago/Turabian Style

Robert Dobosz; Janina Kabatc. 2015. "Corrigendum to “The N-(2-carboxyethyl)hemicyanine dyes. Synthesis, spectroscopic and quantum-chemical studies” [J. Mol. Liq. 202 (2015) 141–147, doi:10.1016/j.molliq.2014.12.019]." Journal of Molecular Liquids 204, no. : 270.

Journal article
Published: 01 April 2015 in Journal of Molecular Liquids
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ACS Style

Robert Dobosz; Janina Kabatc. Corrigendum to “The N-(2-Carboxyethyl)hemicyanine dyes. Synthesis, properties and quantum-chemical calculations” [J. Mol. Liq. 202 (2015) 141–147]. Journal of Molecular Liquids 2015, 204, 269 .

AMA Style

Robert Dobosz, Janina Kabatc. Corrigendum to “The N-(2-Carboxyethyl)hemicyanine dyes. Synthesis, properties and quantum-chemical calculations” [J. Mol. Liq. 202 (2015) 141–147]. Journal of Molecular Liquids. 2015; 204 ():269.

Chicago/Turabian Style

Robert Dobosz; Janina Kabatc. 2015. "Corrigendum to “The N-(2-Carboxyethyl)hemicyanine dyes. Synthesis, properties and quantum-chemical calculations” [J. Mol. Liq. 202 (2015) 141–147]." Journal of Molecular Liquids 204, no. : 269.

Journal article
Published: 01 February 2015 in Journal of Molecular Liquids
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ACS Style

Robert Dobosz; Janina Kabatc. The N-(2-carboxyethyl)hemicyanine dyes. Synthesis, properties and quantum-chemical calculations. Journal of Molecular Liquids 2015, 202, 141 -147.

AMA Style

Robert Dobosz, Janina Kabatc. The N-(2-carboxyethyl)hemicyanine dyes. Synthesis, properties and quantum-chemical calculations. Journal of Molecular Liquids. 2015; 202 ():141-147.

Chicago/Turabian Style

Robert Dobosz; Janina Kabatc. 2015. "The N-(2-carboxyethyl)hemicyanine dyes. Synthesis, properties and quantum-chemical calculations." Journal of Molecular Liquids 202, no. : 141-147.

Journal article
Published: 30 November 2014 in Journal of Theoretical and Computational Chemistry
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B3LYP/maug-cc-pVTZ and MP2/maug-cc-pVTZ calculations show that 3,4-dihydro-quinazoline and its 2- and/or 4-methyl and -phenyl substituted derivatives in solution (chloroform, DMSO, methanol) are only by 0.3 kcal/mol–2.2 kcal/mol more stable than the respective tautomeric 1,4-dihydroquinazolines (the available literature experimental stability data are not coherent). In the gas phase, 2- and/or 4-substituted tautomers of 3,4-dihydroquinazoline are also energetically preferred (B3LYP/maug-cc-pVTZ, MP2/maug-cc-pVTZ and CCSD/cc-pVDZ calculations lead to the same conclusion). In vacuum, 1,4-dihydro tautomer is by 0.1 kcal/mol–0.2 kcal/mol more stable only for unsubstituted dihydro-quinazoline. The observed tautomeric preference was found almost independent on substitution and solvent used. The optimization procedure used shows that the pyrimidine ring in dihydropyrimidines studied is not planar. Noncoplanarity of the 2-phenyl ring and C = N bond in the respective compounds studied is responsible for the weakened conjugation of these two moieties.

ACS Style

Robert Dobosz; Ryszard Gawinecki. Quantum chemical prediction of structure and stability of the benzodihydropyrimidine tautomers. Journal of Theoretical and Computational Chemistry 2014, 13, 1450056 .

AMA Style

Robert Dobosz, Ryszard Gawinecki. Quantum chemical prediction of structure and stability of the benzodihydropyrimidine tautomers. Journal of Theoretical and Computational Chemistry. 2014; 13 (7):1450056.

Chicago/Turabian Style

Robert Dobosz; Ryszard Gawinecki. 2014. "Quantum chemical prediction of structure and stability of the benzodihydropyrimidine tautomers." Journal of Theoretical and Computational Chemistry 13, no. 7: 1450056.

Journal article
Published: 05 June 2013 in Journal of the Iranian Chemical Society
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1H, 13C, 15N and 17O NMR chemical shifts are used for the characterization of the intramolecular interactions in several nitramines of the Me2N-G-NO2 type. The charge of lone electron pair of the amino group in N,N-dimethylnitramine, N,N-dimethyl-2-nitroethenamine, N,N-dimethyl-p-nitroaniline, 4-nitro-β-dimethylaminostyrene, 4-N,N-dimethylamino-β-nitrostyrene, 4-(N,N-dimethylamino)-4′-nitrobiphenyl, and 4-(N,N-dimethylamino)-4′-nitrostilbene is transferred not only to the nitro oxygens, but also to the vinylene and benzene carbons of the G spacer and to N-methyl carbons as well. Decreased nuclear shielding is found to be qualitatively related to the decreased atomic charge around a nucleus. This finding was further verified and quantified by comparison of the NMR data with those obtained by ab initio quantum chemical calculations. 17O NMR chemical shift changes seem to be more significant when the interacting NMe2 and NO2 groups are separated by a short spacer. On the other hand, 15N NMR chemical shifts suggest that a decrease of the charge at the amino nitrogen is not related to the length of the spacer alone. A lack of the linear dependence between the 17Onitro and 15Namino chemical shifts suggests that the charge lost by the amino nitrogen was only partially gained by the oxygens in the nitro group. The increased shieldings of the aryl carbons in 4-(N,N-dimethylamino)-4′-nitrobiphenyl indicate that atoms of the p,p-biphenylene spacer also gain some charge originating from the amino nitrogen. 3 J H,H spin–spin coupling constant shows that among different vinylene compounds, the charge transfer to the nitro group is practically effective only in N,N-dimethyl-2-nitroethenamine where the bond between the vinylene carbons is significantly of low order by character. The calculated Natural Population Analysis (NPA) data confirms that except the nitro oxygens, other atoms that receive the negative charge lost by NMe2 in the compounds studied are the aryl and N-methyl carbons.

ACS Style

Ryszard Gawinecki; Erkki Kolehmainen; Robert Dobosz; Hossein Loghmani Khouzani; Subramanian Chandrasekaran. Intramolecular interactions in nitroamines studied by 1H, 13C, 15N and 17O NMR spectral and quantum chemical methods. Journal of the Iranian Chemical Society 2013, 11, 17 -25.

AMA Style

Ryszard Gawinecki, Erkki Kolehmainen, Robert Dobosz, Hossein Loghmani Khouzani, Subramanian Chandrasekaran. Intramolecular interactions in nitroamines studied by 1H, 13C, 15N and 17O NMR spectral and quantum chemical methods. Journal of the Iranian Chemical Society. 2013; 11 (1):17-25.

Chicago/Turabian Style

Ryszard Gawinecki; Erkki Kolehmainen; Robert Dobosz; Hossein Loghmani Khouzani; Subramanian Chandrasekaran. 2013. "Intramolecular interactions in nitroamines studied by 1H, 13C, 15N and 17O NMR spectral and quantum chemical methods." Journal of the Iranian Chemical Society 11, no. 1: 17-25.

Original paper
Published: 18 May 2013 in Journal of Molecular Modeling
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Density functional theory (DFT) calculations at the B3LYP/6-311+G(d,p) level show that 4,6-di(pyridin-2-yl)cyclohexane-1,3-dione is a labile compound. On the other hand, its dienolimine tautomer (4,6-di(pyridin-2-yl)cyclohaxa-1,3-diene-1,3-diol) seems stable enough to be present in vacuum. Alternatively the equilibriated species are (i) dienolimine and enolimine-enaminone ((6Z)-3-hydroxy-6-(pyridin-2(1H)-ylidene)-4-(pyridine-2-yl)cyclohex-3-enone) or (ii) dienolimine, enolimine-enaminone and dienaminone ((4Z,6Z)-4,6-di(pyridin-2(1H)-ylidene)cyclohexane-1,3-dione). Benzoannulation of the pyridine ring at position 5,6 was found to increase the contribution of the tautomers which contain the enaminone moiety. Energies of the transition states between the stable tautomers were also calculated in order to estimate activation energy of the proton transfer. Values of the geometry based harmonic oscillator model of aromaticity (HOMA) index and Laplacian of the electron density in the hydrogen bond critical point (based on quantum theory of atom in molecules) shows that the enaminone moiety in the tautomers studied are stabilized by stronger intramolecular hydrogen bond than this present in the enolimine moiety.

ACS Style

Robert Dobosz; Ryszard Gawinecki. Effect of benzoannulation on tautomeric preferences of 4,6-di(pyridin-2-yl)cyclohexane-1,3-dione. Journal of Molecular Modeling 2013, 19, 3397 -3402.

AMA Style

Robert Dobosz, Ryszard Gawinecki. Effect of benzoannulation on tautomeric preferences of 4,6-di(pyridin-2-yl)cyclohexane-1,3-dione. Journal of Molecular Modeling. 2013; 19 (8):3397-3402.

Chicago/Turabian Style

Robert Dobosz; Ryszard Gawinecki. 2013. "Effect of benzoannulation on tautomeric preferences of 4,6-di(pyridin-2-yl)cyclohexane-1,3-dione." Journal of Molecular Modeling 19, no. 8: 3397-3402.

Short communication
Published: 31 July 2011 in Computational and Theoretical Chemistry
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ACS Style

Robert Dobosz; Ryszard Gawinecki. Computational note on the tautomeric preferences of 2,7-di(pyridin-2-yl)-and 2,7-di(quinolin-2-yl)hexahydronaphthalene-1,8-diones. Computational and Theoretical Chemistry 2011, 967, 211 -212.

AMA Style

Robert Dobosz, Ryszard Gawinecki. Computational note on the tautomeric preferences of 2,7-di(pyridin-2-yl)-and 2,7-di(quinolin-2-yl)hexahydronaphthalene-1,8-diones. Computational and Theoretical Chemistry. 2011; 967 (1):211-212.

Chicago/Turabian Style

Robert Dobosz; Ryszard Gawinecki. 2011. "Computational note on the tautomeric preferences of 2,7-di(pyridin-2-yl)-and 2,7-di(quinolin-2-yl)hexahydronaphthalene-1,8-diones." Computational and Theoretical Chemistry 967, no. 1: 211-212.

Journal article
Published: 13 July 2011 in Structural Chemistry
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Structural data for five nitroamines of general formula Me2N–G–NO2 show effectiveness of the ground-state charge transfer to be most and least efficient in N,N-dimethylnitramine and in 4-N,N-dimethylamino-β-nitrostyrene, respectively. Electron-donor power of the amino nitrogen atom in the latter compound is less than that in 4-nitro-β-N,N-dimethylaminostyrene (these two compounds are isomers). Natural population analysis shows that the charge transfer from the amino to the nitro oxygen atoms is most effective in N,N-dimethylnitramine, Me2N–NO2. The nitro oxygen atoms are not the only acceptors of the negative charge lost by the amino nitrogen atom. The nitro group in two substituted nitrobenzenes studied was found to be independent on substituent (nitro group attached to the benzene ring withdraws a constant electron density regardless the substitution).

ACS Style

Ryszard Gawinecki; Erkki Kolehmainen; Robert Dobosz. Structure-based evaluation of the resonance interactions and effectiveness of the charge transfer in nitroamines. Structural Chemistry 2011, 22, 1379 -1383.

AMA Style

Ryszard Gawinecki, Erkki Kolehmainen, Robert Dobosz. Structure-based evaluation of the resonance interactions and effectiveness of the charge transfer in nitroamines. Structural Chemistry. 2011; 22 (6):1379-1383.

Chicago/Turabian Style

Ryszard Gawinecki; Erkki Kolehmainen; Robert Dobosz. 2011. "Structure-based evaluation of the resonance interactions and effectiveness of the charge transfer in nitroamines." Structural Chemistry 22, no. 6: 1379-1383.

Journal article
Published: 01 January 2011 in Journal of Molecular Structure
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ACS Style

Janina Kabatc; Agnieszka Bajorek; Robert Dobosz. Bichromophoric hemicyanine dyes as fluorescence probes applied for monitoring of the photochemically initiated polymerization. Journal of Molecular Structure 2011, 985, 95 -104.

AMA Style

Janina Kabatc, Agnieszka Bajorek, Robert Dobosz. Bichromophoric hemicyanine dyes as fluorescence probes applied for monitoring of the photochemically initiated polymerization. Journal of Molecular Structure. 2011; 985 (1):95-104.

Chicago/Turabian Style

Janina Kabatc; Agnieszka Bajorek; Robert Dobosz. 2011. "Bichromophoric hemicyanine dyes as fluorescence probes applied for monitoring of the photochemically initiated polymerization." Journal of Molecular Structure 985, no. 1: 95-104.

Journal article
Published: 31 December 2010 in Journal of Molecular Modeling
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The 2-[1H]-pyridone/2-hydroxypyridine tautomeric pair and its 6-substituted complexes have been studied with the use of DFT(M05) method. The intermolecular interaction energy has been calculated and discussed in the light of secondary interaction concept. The attractive secondary interactions of O/NH and O/OH type and OH/NH and OH/OH repulsions have been analyzed in terms of stabilizing or destabilizing influence on intermolecular behavior. The transition states of the double proton transfer reaction have been found and the energy of activation has been determined. The activation energy of the proton transfer reaction, geometry of the complexes and transition states show NH(2) and/or OH groups influence the properties of complexes and transition states. The HOMA index of aromaticity was applied to describe the π-electron delocalization in the heterocyclic rings.

ACS Style

Borys Ośmiałowski; Robert Dobosz. The influence of secondary interactions on complex stability and double proton transfer reaction in 2-[1H]-pyridone/2-hydroxypyridine dimers. Journal of Molecular Modeling 2010, 17, 2491 -2500.

AMA Style

Borys Ośmiałowski, Robert Dobosz. The influence of secondary interactions on complex stability and double proton transfer reaction in 2-[1H]-pyridone/2-hydroxypyridine dimers. Journal of Molecular Modeling. 2010; 17 (10):2491-2500.

Chicago/Turabian Style

Borys Ośmiałowski; Robert Dobosz. 2010. "The influence of secondary interactions on complex stability and double proton transfer reaction in 2-[1H]-pyridone/2-hydroxypyridine dimers." Journal of Molecular Modeling 17, no. 10: 2491-2500.

Journal article
Published: 16 December 2010 in The Journal of Physical Chemistry A
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Intermolecular hydrogen bonds between 2,6-bis(acylamino)pyridines and dipyridin-2-ylamine as well as 4,4-dimethylpiperidine-2,6-dione are responsible for relatively strong interactions between these species. Association has been found to be significantly affected by the size of acyl substituent (chemical shift of the NH proton was used as the main probe in determination of the association constants). Calculations at the DFT level of theory are in line with the experimentally observed results. Calculated energies of the interactions between the complex congeners also show the size of the substituent to affect the association. Conformational changes in the dipyridin-2-ylamine molecule are shown to adapt a geometry suitable for formation of efficient hydrogen bonding.

ACS Style

Borys Ośmiałowski; Erkki Kolehmainen; Ryszard Gawinecki; Robert Dobosz; Reijo Kauppinen. Complexation of 2,6-Bis(acylamino)pyridines with Dipyridin-2-ylamine and 4,4-Dimethylpiperidine-2,6-dione. The Journal of Physical Chemistry A 2010, 114, 12881 -12887.

AMA Style

Borys Ośmiałowski, Erkki Kolehmainen, Ryszard Gawinecki, Robert Dobosz, Reijo Kauppinen. Complexation of 2,6-Bis(acylamino)pyridines with Dipyridin-2-ylamine and 4,4-Dimethylpiperidine-2,6-dione. The Journal of Physical Chemistry A. 2010; 114 (49):12881-12887.

Chicago/Turabian Style

Borys Ośmiałowski; Erkki Kolehmainen; Ryszard Gawinecki; Robert Dobosz; Reijo Kauppinen. 2010. "Complexation of 2,6-Bis(acylamino)pyridines with Dipyridin-2-ylamine and 4,4-Dimethylpiperidine-2,6-dione." The Journal of Physical Chemistry A 114, no. 49: 12881-12887.

Journal article
Published: 09 November 2010 in Structural Chemistry
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Density functional theory (DFT) calculations show that in vacuum such α-diketone as 1-(pyridin-2-yl)-4-(quinolin-2-yl)butane-2,3-dione is much less stable than its enolimine–enaminone ((1Z,3Z)-3-hydroxy-4-(pyridin-2-yl)-1-(quinolin-2(1H)-ylidene)but-3-en-2-one) and dienaminone tautomers ((1Z,3Z)-1-(pyridin-2-yl)-4-(quinolin-2-yl)buta-1,3-diene-2,3-diol). Other its tautomers (multiple basic and acidic centers in their molecules enable multiple proton transfer to take place) are even more labile. Strength of the intramolecular hydrogen bonds and aromatic character of the (quasi)rings [proved by the Harmonic Oscillator Model of Aromaticity (HOMA) index] in their molecules were found to be responsible for the observed tautomeric preferences. Polar and basic solvent disfavors and favors the enolimine and enaminone tautomers, respectively.

ACS Style

Robert Dobosz; Ryszard Gawinecki; Borys Osmialowski. DFT studies on tautomeric preferences of 1-(pyridin-2-yl)-4-(quinolin-2-yl)butane-2,3-dione in the gas phase and in solution. Structural Chemistry 2010, 21, 1283 -1287.

AMA Style

Robert Dobosz, Ryszard Gawinecki, Borys Osmialowski. DFT studies on tautomeric preferences of 1-(pyridin-2-yl)-4-(quinolin-2-yl)butane-2,3-dione in the gas phase and in solution. Structural Chemistry. 2010; 21 (6):1283-1287.

Chicago/Turabian Style

Robert Dobosz; Ryszard Gawinecki; Borys Osmialowski. 2010. "DFT studies on tautomeric preferences of 1-(pyridin-2-yl)-4-(quinolin-2-yl)butane-2,3-dione in the gas phase and in solution." Structural Chemistry 21, no. 6: 1283-1287.

Journal article
Published: 30 September 2010 in The Journal of Physical Chemistry A
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Aggregation of 2-acylaminopyridines and their 6-methyl derivatives in chloroform solution was studied by (1)H, (13)C, and (15)N NMR spectroscopies. The results were compared with (13)C and (15)N CPMAS NMR and IR spectral as well as with X-ray structural data. Intermolecular interactions in solution and in solid state were found to have a similar nature. Relatively strong N(amide)-H···N(pyridine) intermolecular hydrogen bonds enable dimerization to take place. Steric interactions in N-pivaloyl- and N-1-adamantylcarbonyl as well as that caused by the 6-methyl group hinder formation of the dimeric aggregates stabilized by the N(amide)-H···N(pyridine) intermolecular hydrogen bonds. In general, the DFT optimized geometries of the aggregates in chloroform solution are in agreement with the X-ray crystal structures. Wavenumbers of the stretching vibration band of the C═O group were also found indicative of the type of hydrogen bond present in the solid state.

ACS Style

Borys Ośmiałowski; Erkki Kolehmainen; Robert Dobosz; Ryszard Gawinecki; Reijo Kauppinen; Arto Valkonen; Juha Koivukorpi; Kari Rissanen. Self-Organization of 2-Acylaminopyridines in the Solid State and in Solution. The Journal of Physical Chemistry A 2010, 114, 10421 -10426.

AMA Style

Borys Ośmiałowski, Erkki Kolehmainen, Robert Dobosz, Ryszard Gawinecki, Reijo Kauppinen, Arto Valkonen, Juha Koivukorpi, Kari Rissanen. Self-Organization of 2-Acylaminopyridines in the Solid State and in Solution. The Journal of Physical Chemistry A. 2010; 114 (38):10421-10426.

Chicago/Turabian Style

Borys Ośmiałowski; Erkki Kolehmainen; Robert Dobosz; Ryszard Gawinecki; Reijo Kauppinen; Arto Valkonen; Juha Koivukorpi; Kari Rissanen. 2010. "Self-Organization of 2-Acylaminopyridines in the Solid State and in Solution." The Journal of Physical Chemistry A 114, no. 38: 10421-10426.

Journal article
Published: 01 August 2010 in Journal of Molecular Structure
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ACS Style

Robert Dobosz; Agnieszka Skotnicka; Zbigniew Rozwadowski; Teresa Dziembowska; Ryszard Gawinecki. Stability of N-(ortho-hydroxynaphthylmethylene)methylamines and their tautomers. Journal of Molecular Structure 2010, 979, 194 -199.

AMA Style

Robert Dobosz, Agnieszka Skotnicka, Zbigniew Rozwadowski, Teresa Dziembowska, Ryszard Gawinecki. Stability of N-(ortho-hydroxynaphthylmethylene)methylamines and their tautomers. Journal of Molecular Structure. 2010; 979 (1-3):194-199.

Chicago/Turabian Style

Robert Dobosz; Agnieszka Skotnicka; Zbigniew Rozwadowski; Teresa Dziembowska; Ryszard Gawinecki. 2010. "Stability of N-(ortho-hydroxynaphthylmethylene)methylamines and their tautomers." Journal of Molecular Structure 979, no. 1-3: 194-199.