Maija Nissinen | University of Jyväskylä (original) (raw)
Papers by Maija Nissinen
Arkivoc, 2002
Nine novel polychlorinated dihydrocamphenes (1-9) have been isolated from reaction mixtures obtai... more Nine novel polychlorinated dihydrocamphenes (1-9) have been isolated from reaction mixtures obtained by the chlorination of lower chlorinated monoterpenes. These compounds are potential congeners of insecticide toxaphene. The 1 H and 13 C NMR spectra of 1-9 have been assigned by means of 1 H, 1 H DQF COSY (double-quantum filtered correlation spectroscopy), 1 H, 1 H ROESY (rotating frame nuclear Overhauser effect spectroscopy), PFG 1 H, 13 C HMQC (pulsed field gradient heteronuclear multiple quantum coherence), 1 H, 13 C HMBC (heteronuclear multiple bond correlation) experiments, and computer aided 1 H NMR spectral analysis. In the case of 2, the structure has been determined by X-ray methods. Full geometry optimizations have been performed at the ab initio HF/6-31G* level for a comparison with the conformational and structural properties obtained from the NMR-and X-ray experiments. The optimized geometries are in excellent agreement with the experimental structures. In addition, rotation barriers of compounds 7 and 9 have been characterized with the semiempirical AM1 method. The gauge-including atomic orbital (GIAO) method have been employed to calculate 13 C chemical shifts of 1-9 using density functional theory (DFT) at the B3LYP/6-311G* level and the HF/6-31G* optimized structures as geometry input. A comparison of the calculated and experimental data yielded a regression equation, which with added indicator variable (the number of chlorine atoms attached to each carbon) is capable of the accurate prediction of carbon chemical shifts for these compounds.
Nanoscale, 2012
A simple one-pot method for the preparation of subnanometre-size benzotriazolate (BTA) protected ... more A simple one-pot method for the preparation of subnanometre-size benzotriazolate (BTA) protected copper clusters, Cu(n)BTA(m), is reported. The clusters were analyzed by optical and infrared spectroscopy, mass spectrometry and transmission electron microscopy together with computational methods. We suggest a structural motif where the copper core of the Cu(n)BTA(m) clusters is protected by BTA-Cu(i)-BTA units.
New Journal of Chemistry, 2009
... Kaisa Helttunen, Piotr Prus, Minna Luostarinen and Maija Nissinen*. Department of Chemistry, ... more ... Kaisa Helttunen, Piotr Prus, Minna Luostarinen and Maija Nissinen*. Department of Chemistry, Nanoscience Center, University of Jyväskylä, PO Box 35, FIN-40014 JYU, Finland. ... 26, DA Leigh, P. Linnane, RG Pritchard and G. Jackson, J. Chem. Soc., Chem. ...
Chemistry-an Asian Journal, Feb 6, 2012
Mixed-donor atom tetramethoxy resorcinarene bis-thiacrown hosts, in which the crown unit contains... more Mixed-donor atom tetramethoxy resorcinarene bis-thiacrown hosts, in which the crown unit contains both hard oxygen and soft sulfur donor atoms, were synthesized for soft metal cation binding. The binding properties were investigated both in solution and in the solid state by NMR spectroscopy and X-ray crystallography. It was found that the resorcinarene bis-thiacrowns were able to complex silver cations with remarkable affinity forming readily 1:2 host-guest complexes in solution. The solid state structures also revealed that the bis-thiacrowns form silver complexes in an unanticipated endo- and exo-cavity fashion within the same host molecule. Both the solution and solid state studies indicated the sulfur atoms to be the major contributing donor atoms in forming the binding interactions with silver cations.
JYX, Sep 7, 2017
UCUZOK : 6,12,18,24-tetramethoxy-2,8,14,20-tetranonyl-4,10,16,22-tetrahydroxycalix[4]arene propan... more UCUZOK : 6,12,18,24-tetramethoxy-2,8,14,20-tetranonyl-4,10,16,22-tetrahydroxycalix[4]arene propan-2-ol solvate Space Group: P-1, Cell: a 12.27090(10)A b 13.96500(10)A c 19.53620(10)A, α 83.2880(1)° β 89.0250(1)° γ 84.9650(1)° Work published 2017 via Cambridge Crystallographic Data Centre.
JYX, Sep 7, 2017
UDAKOC : diaqua-(μ-1,13-dioxa-4,7,10,16,19,22-hexaazacyclotetracosane)-bis(perchlorato)-di-copper... more UDAKOC : diaqua-(μ-1,13-dioxa-4,7,10,16,19,22-hexaazacyclotetracosane)-bis(perchlorato)-di-copper(ii) diperchlorate tetrahydrate Space Group: P21/c, Cell: a 11.8763(3)A b 13.9146(4)A c 13.4024(4)A, α 90.00° β 123.439(2)° γ 90.00° Work published 2017 via Cambridge Crystallographic Data Centre.
Chemistry: A European Journal, Apr 30, 2020
The synthesis of tetramethoxyresorcinarene podands bearing p-toluenea rms connected by-SO 3-(1)a ... more The synthesis of tetramethoxyresorcinarene podands bearing p-toluenea rms connected by-SO 3-(1)a nd-CH 2 O-(2)l inkers is presented herein. In the solid state, the resorcinarene podand 1 forms an intramolecular self-inclusion complex with the pendant p-toluene group of a podand arm, whereas the resorcinarenep odand 2 does not show self-inclusion. The conformations of the flexible resorcinarene podands in solution were investigated by variabletemperaturee xperimentsu sing 1D and2 DN MR spectroscopic techniques as well as by computational methods, including aconformational search and subsequent DFT optimisation of representative structures. The 1 HNMR spectrao f1 and 2 at room temperature showasingle set of proton signals that are in agreement with C 4v symmetry. At low temperatures, the molecules exist as am ixture of boat conformations featuring slow exchange on the NMR timescale. Energy barriers (DG°2 98)o f5 5.5 and 52.0 kJ mol À1 were calculated fort he boat-to-boat exchange of 1 and 2,r espectively. The results of the ROESY experiments performed at 193 K and computational modelling suggestt hat in solution the resorcinarene podand 1 adopts as imilarc onformationt o that presenti ni ts crystal structure,w hereas podand 2 populates am ore versatile range of conformations in solution.
CrystEngComm, 2012
Tetramethoxy resorcinarene bis-crown-5 (1) was previously prepared by us. 1 Single crystals of th... more Tetramethoxy resorcinarene bis-crown-5 (1) was previously prepared by us. 1 Single crystals of the complexes were grown by slow evaporation of alcohol solutions (methanol, ethanol and i-or n-propanol) of 1 with excess of AgPF 6 at room temperature. Crystal Structure Data and Details Data were recorded on a Nonius Kappa CCD diffractometer with Apex II detector using graphite monochromatized CuK α [λ(CuK α) = 1.54178 Å] radiation at a temperature of 173.0 K. The data were processed with Denzo-SMN v0.97.638. 2 The structures were solved by direct methods (SHELXS-97 3) and refinements based on F 2 were made by full-matrix least-squares techniques (SHELXL-97 4). The hydrogen atoms were calculated to their idealized positions with isotropic temperature factors (1.2 or 1.5 times the C temperature factor) and refined as riding atoms. Hydroxyl hydrogens were located from the difference Fourier map when possible and the bond distances were fixed (DFIX 0.84) when necessary. Absorption correction 5 was made to all structures. CCDC numbers 813688-813691 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request.cif.
European Journal of Organic Chemistry, Dec 1, 2009
The synthesis and structure of a neutral resorcinarene host bearing four amine-functionalized sid... more The synthesis and structure of a neutral resorcinarene host bearing four amine-functionalized side arms is described. The anion binding properties were investigated in solution by 1 H NMR spectroscopic titration and diffusion experiments and in the gas phase by mass spectrometric studies. It was observed that in solution 1:2 (host/guest) complexes were
JYX, Sep 18, 2017
UCUBIG : N,N'-bis(2-(benzoylamino)phenyl)pyridine-2,6-dicarboxamide chloroform solvate Space ... more UCUBIG : N,N'-bis(2-(benzoylamino)phenyl)pyridine-2,6-dicarboxamide chloroform solvate Space Group: P21/c, Cell: a 13.8622(4)A b 19.5031(4)A c 11.3742(5)A, α 90° β 93.5030(14)° γ 90°, Work published 2016 via Cambridge Crystallographic Data Centre.
Related Article: Riia Annala, Aku Suhonen, Heikki Laakkonen, Perttu Permi, Maija Nissinen|2017|Ch... more Related Article: Riia Annala, Aku Suhonen, Heikki Laakkonen, Perttu Permi, Maija Nissinen|2017|Chem.-Eur.J.|23|16671|doi:10.1002/chem.201703985
Related Article: Riia Annala, Aku Suhonen, Heikki Laakkonen, Perttu Permi, Maija Nissinen|2017|Ch... more Related Article: Riia Annala, Aku Suhonen, Heikki Laakkonen, Perttu Permi, Maija Nissinen|2017|Chem.-Eur.J.|23|16671|doi:10.1002/chem.201703985
Crystal Growth & Design, May 19, 2015
A disulfonamide compound with bulky aromatic side chains was prepared and its properties as a pot... more A disulfonamide compound with bulky aromatic side chains was prepared and its properties as a potential building block for foldamers evaluated. Two different solvate crystal forms of the compound were identified and compared to the structures of an analogous oligoamide and related disulfonamides. The disulfonamide is unfolded in one of the solvates, whereas in the other one, a loosely folded conformer stabilized by an intramolecular hydrogen bond is found. Density functional calculations indicated that the loosely folded conformer is slightly more stable than its unfolded isomer. The calculations also identified a third, more tightly folded and more extensively hydrogen bonded conformer that is even lower in energy.
European Journal of Organic Chemistry, Jan 30, 2013
O‐Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of pa... more O‐Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of partially O‐alkylated resorcinarene derivatives with terminal alkyne functionality. The degree of alkylation was affected by the reactivity of the alkylating halide used. NMR spectroscopy proved to be an ideal tool for analyzing the complex reaction mixtures and the isolated products based on the symmetry and degree of alkylation of the resorcinarene derivatives. Single‐crystal X‐ray diffraction studies furthermore showed diversity in the self‐assembly of the various O‐alkylation products that was greatly affected by the degree of alkylation, as well as the nature of the alkyne moiety.
Organic and Biomolecular Chemistry, 2011
Zeitschrift Fur Kristallographie-new Crystal Structures, Apr 1, 2005
C19H12M0O5R11, monoclinic, Pl2\ln\ (no. 14),
CrystEngComm, 2012
The crystal structures and molecular conformations of two foldamer-type oligoamides were analyzed... more The crystal structures and molecular conformations of two foldamer-type oligoamides were analyzed. One polymorphic form and seven solvates were found for N 1 ,N 3-bis(2-benzamidophenyl)benzene-1,3dicarboxamide (the benzene variant), and two polymorphic forms and six solvates for N 2 ,N 6-bis(2benzamidophenyl)pyridine-2,6-dicarboxamide (the pyridine variant). Three crystal structures of the benzene variant and six structures of the pyridine variant were solved using single crystal X-ray diffraction. The crystal structures showed that the different modes of intramolecular hydrogen bonding strongly affect the conformation and folding of the molecules, which is most evidently seen with the strongly folded helical structure of the pyridine variant. NOESY experiments suggest that the intramolecular hydrogen bonding is stable enough to retain a folded or partially folded conformation even in solution. 65 CREATED USING THE RSC ARTICLE TEMPLATE (VER. 3.0)-SEE WWW.RSC.ORG/ELECTRONICFILES FOR DETAILS
CrystEngComm, 2012
The synthesis and characterization of new bromine substituted pyridine and benzyl functionalized ... more The synthesis and characterization of new bromine substituted pyridine and benzyl functionalized tetramethoxy resorcinarene tetrapodands are described and their solid state structural properties and interactions were studied by single crystal X-ray crystallography. Three different crystal structures were obtained for the pyridine derivative and one for the benzyl derivative, which revealed that the interactions of the bromine substituent have explicitly an effect on the crystal packing of the resorcinarene molecules. One of the structures obtained had very interesting halogen-halogen interaction with the same geometry as is generally found for compounds used in nonlinear optical studies.
Arkivoc, 2002
Nine novel polychlorinated dihydrocamphenes (1-9) have been isolated from reaction mixtures obtai... more Nine novel polychlorinated dihydrocamphenes (1-9) have been isolated from reaction mixtures obtained by the chlorination of lower chlorinated monoterpenes. These compounds are potential congeners of insecticide toxaphene. The 1 H and 13 C NMR spectra of 1-9 have been assigned by means of 1 H, 1 H DQF COSY (double-quantum filtered correlation spectroscopy), 1 H, 1 H ROESY (rotating frame nuclear Overhauser effect spectroscopy), PFG 1 H, 13 C HMQC (pulsed field gradient heteronuclear multiple quantum coherence), 1 H, 13 C HMBC (heteronuclear multiple bond correlation) experiments, and computer aided 1 H NMR spectral analysis. In the case of 2, the structure has been determined by X-ray methods. Full geometry optimizations have been performed at the ab initio HF/6-31G* level for a comparison with the conformational and structural properties obtained from the NMR-and X-ray experiments. The optimized geometries are in excellent agreement with the experimental structures. In addition, rotation barriers of compounds 7 and 9 have been characterized with the semiempirical AM1 method. The gauge-including atomic orbital (GIAO) method have been employed to calculate 13 C chemical shifts of 1-9 using density functional theory (DFT) at the B3LYP/6-311G* level and the HF/6-31G* optimized structures as geometry input. A comparison of the calculated and experimental data yielded a regression equation, which with added indicator variable (the number of chlorine atoms attached to each carbon) is capable of the accurate prediction of carbon chemical shifts for these compounds.
Nanoscale, 2012
A simple one-pot method for the preparation of subnanometre-size benzotriazolate (BTA) protected ... more A simple one-pot method for the preparation of subnanometre-size benzotriazolate (BTA) protected copper clusters, Cu(n)BTA(m), is reported. The clusters were analyzed by optical and infrared spectroscopy, mass spectrometry and transmission electron microscopy together with computational methods. We suggest a structural motif where the copper core of the Cu(n)BTA(m) clusters is protected by BTA-Cu(i)-BTA units.
New Journal of Chemistry, 2009
... Kaisa Helttunen, Piotr Prus, Minna Luostarinen and Maija Nissinen*. Department of Chemistry, ... more ... Kaisa Helttunen, Piotr Prus, Minna Luostarinen and Maija Nissinen*. Department of Chemistry, Nanoscience Center, University of Jyväskylä, PO Box 35, FIN-40014 JYU, Finland. ... 26, DA Leigh, P. Linnane, RG Pritchard and G. Jackson, J. Chem. Soc., Chem. ...
Chemistry-an Asian Journal, Feb 6, 2012
Mixed-donor atom tetramethoxy resorcinarene bis-thiacrown hosts, in which the crown unit contains... more Mixed-donor atom tetramethoxy resorcinarene bis-thiacrown hosts, in which the crown unit contains both hard oxygen and soft sulfur donor atoms, were synthesized for soft metal cation binding. The binding properties were investigated both in solution and in the solid state by NMR spectroscopy and X-ray crystallography. It was found that the resorcinarene bis-thiacrowns were able to complex silver cations with remarkable affinity forming readily 1:2 host-guest complexes in solution. The solid state structures also revealed that the bis-thiacrowns form silver complexes in an unanticipated endo- and exo-cavity fashion within the same host molecule. Both the solution and solid state studies indicated the sulfur atoms to be the major contributing donor atoms in forming the binding interactions with silver cations.
JYX, Sep 7, 2017
UCUZOK : 6,12,18,24-tetramethoxy-2,8,14,20-tetranonyl-4,10,16,22-tetrahydroxycalix[4]arene propan... more UCUZOK : 6,12,18,24-tetramethoxy-2,8,14,20-tetranonyl-4,10,16,22-tetrahydroxycalix[4]arene propan-2-ol solvate Space Group: P-1, Cell: a 12.27090(10)A b 13.96500(10)A c 19.53620(10)A, α 83.2880(1)° β 89.0250(1)° γ 84.9650(1)° Work published 2017 via Cambridge Crystallographic Data Centre.
JYX, Sep 7, 2017
UDAKOC : diaqua-(μ-1,13-dioxa-4,7,10,16,19,22-hexaazacyclotetracosane)-bis(perchlorato)-di-copper... more UDAKOC : diaqua-(μ-1,13-dioxa-4,7,10,16,19,22-hexaazacyclotetracosane)-bis(perchlorato)-di-copper(ii) diperchlorate tetrahydrate Space Group: P21/c, Cell: a 11.8763(3)A b 13.9146(4)A c 13.4024(4)A, α 90.00° β 123.439(2)° γ 90.00° Work published 2017 via Cambridge Crystallographic Data Centre.
Chemistry: A European Journal, Apr 30, 2020
The synthesis of tetramethoxyresorcinarene podands bearing p-toluenea rms connected by-SO 3-(1)a ... more The synthesis of tetramethoxyresorcinarene podands bearing p-toluenea rms connected by-SO 3-(1)a nd-CH 2 O-(2)l inkers is presented herein. In the solid state, the resorcinarene podand 1 forms an intramolecular self-inclusion complex with the pendant p-toluene group of a podand arm, whereas the resorcinarenep odand 2 does not show self-inclusion. The conformations of the flexible resorcinarene podands in solution were investigated by variabletemperaturee xperimentsu sing 1D and2 DN MR spectroscopic techniques as well as by computational methods, including aconformational search and subsequent DFT optimisation of representative structures. The 1 HNMR spectrao f1 and 2 at room temperature showasingle set of proton signals that are in agreement with C 4v symmetry. At low temperatures, the molecules exist as am ixture of boat conformations featuring slow exchange on the NMR timescale. Energy barriers (DG°2 98)o f5 5.5 and 52.0 kJ mol À1 were calculated fort he boat-to-boat exchange of 1 and 2,r espectively. The results of the ROESY experiments performed at 193 K and computational modelling suggestt hat in solution the resorcinarene podand 1 adopts as imilarc onformationt o that presenti ni ts crystal structure,w hereas podand 2 populates am ore versatile range of conformations in solution.
CrystEngComm, 2012
Tetramethoxy resorcinarene bis-crown-5 (1) was previously prepared by us. 1 Single crystals of th... more Tetramethoxy resorcinarene bis-crown-5 (1) was previously prepared by us. 1 Single crystals of the complexes were grown by slow evaporation of alcohol solutions (methanol, ethanol and i-or n-propanol) of 1 with excess of AgPF 6 at room temperature. Crystal Structure Data and Details Data were recorded on a Nonius Kappa CCD diffractometer with Apex II detector using graphite monochromatized CuK α [λ(CuK α) = 1.54178 Å] radiation at a temperature of 173.0 K. The data were processed with Denzo-SMN v0.97.638. 2 The structures were solved by direct methods (SHELXS-97 3) and refinements based on F 2 were made by full-matrix least-squares techniques (SHELXL-97 4). The hydrogen atoms were calculated to their idealized positions with isotropic temperature factors (1.2 or 1.5 times the C temperature factor) and refined as riding atoms. Hydroxyl hydrogens were located from the difference Fourier map when possible and the bond distances were fixed (DFIX 0.84) when necessary. Absorption correction 5 was made to all structures. CCDC numbers 813688-813691 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request.cif.
European Journal of Organic Chemistry, Dec 1, 2009
The synthesis and structure of a neutral resorcinarene host bearing four amine-functionalized sid... more The synthesis and structure of a neutral resorcinarene host bearing four amine-functionalized side arms is described. The anion binding properties were investigated in solution by 1 H NMR spectroscopic titration and diffusion experiments and in the gas phase by mass spectrometric studies. It was observed that in solution 1:2 (host/guest) complexes were
JYX, Sep 18, 2017
UCUBIG : N,N'-bis(2-(benzoylamino)phenyl)pyridine-2,6-dicarboxamide chloroform solvate Space ... more UCUBIG : N,N'-bis(2-(benzoylamino)phenyl)pyridine-2,6-dicarboxamide chloroform solvate Space Group: P21/c, Cell: a 13.8622(4)A b 19.5031(4)A c 11.3742(5)A, α 90° β 93.5030(14)° γ 90°, Work published 2016 via Cambridge Crystallographic Data Centre.
Related Article: Riia Annala, Aku Suhonen, Heikki Laakkonen, Perttu Permi, Maija Nissinen|2017|Ch... more Related Article: Riia Annala, Aku Suhonen, Heikki Laakkonen, Perttu Permi, Maija Nissinen|2017|Chem.-Eur.J.|23|16671|doi:10.1002/chem.201703985
Related Article: Riia Annala, Aku Suhonen, Heikki Laakkonen, Perttu Permi, Maija Nissinen|2017|Ch... more Related Article: Riia Annala, Aku Suhonen, Heikki Laakkonen, Perttu Permi, Maija Nissinen|2017|Chem.-Eur.J.|23|16671|doi:10.1002/chem.201703985
Crystal Growth & Design, May 19, 2015
A disulfonamide compound with bulky aromatic side chains was prepared and its properties as a pot... more A disulfonamide compound with bulky aromatic side chains was prepared and its properties as a potential building block for foldamers evaluated. Two different solvate crystal forms of the compound were identified and compared to the structures of an analogous oligoamide and related disulfonamides. The disulfonamide is unfolded in one of the solvates, whereas in the other one, a loosely folded conformer stabilized by an intramolecular hydrogen bond is found. Density functional calculations indicated that the loosely folded conformer is slightly more stable than its unfolded isomer. The calculations also identified a third, more tightly folded and more extensively hydrogen bonded conformer that is even lower in energy.
European Journal of Organic Chemistry, Jan 30, 2013
O‐Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of pa... more O‐Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of partially O‐alkylated resorcinarene derivatives with terminal alkyne functionality. The degree of alkylation was affected by the reactivity of the alkylating halide used. NMR spectroscopy proved to be an ideal tool for analyzing the complex reaction mixtures and the isolated products based on the symmetry and degree of alkylation of the resorcinarene derivatives. Single‐crystal X‐ray diffraction studies furthermore showed diversity in the self‐assembly of the various O‐alkylation products that was greatly affected by the degree of alkylation, as well as the nature of the alkyne moiety.
Organic and Biomolecular Chemistry, 2011
Zeitschrift Fur Kristallographie-new Crystal Structures, Apr 1, 2005
C19H12M0O5R11, monoclinic, Pl2\ln\ (no. 14),
CrystEngComm, 2012
The crystal structures and molecular conformations of two foldamer-type oligoamides were analyzed... more The crystal structures and molecular conformations of two foldamer-type oligoamides were analyzed. One polymorphic form and seven solvates were found for N 1 ,N 3-bis(2-benzamidophenyl)benzene-1,3dicarboxamide (the benzene variant), and two polymorphic forms and six solvates for N 2 ,N 6-bis(2benzamidophenyl)pyridine-2,6-dicarboxamide (the pyridine variant). Three crystal structures of the benzene variant and six structures of the pyridine variant were solved using single crystal X-ray diffraction. The crystal structures showed that the different modes of intramolecular hydrogen bonding strongly affect the conformation and folding of the molecules, which is most evidently seen with the strongly folded helical structure of the pyridine variant. NOESY experiments suggest that the intramolecular hydrogen bonding is stable enough to retain a folded or partially folded conformation even in solution. 65 CREATED USING THE RSC ARTICLE TEMPLATE (VER. 3.0)-SEE WWW.RSC.ORG/ELECTRONICFILES FOR DETAILS
CrystEngComm, 2012
The synthesis and characterization of new bromine substituted pyridine and benzyl functionalized ... more The synthesis and characterization of new bromine substituted pyridine and benzyl functionalized tetramethoxy resorcinarene tetrapodands are described and their solid state structural properties and interactions were studied by single crystal X-ray crystallography. Three different crystal structures were obtained for the pyridine derivative and one for the benzyl derivative, which revealed that the interactions of the bromine substituent have explicitly an effect on the crystal packing of the resorcinarene molecules. One of the structures obtained had very interesting halogen-halogen interaction with the same geometry as is generally found for compounds used in nonlinear optical studies.