A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene
Letzel M, Schäfer C, Novara FR, Speranza M, Rozhenko AB, Schoeller W, Mattay J (2008)
Journal of Mass Spectrometry 43(11): 1553-1564.
Zeitschriftenaufsatz
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Autor*in
Letzel, MatthiasUniBi;
Schäfer, Christian;
Novara, Francesca R.;
Speranza, Maurizio;
Rozhenko, Alexander B.;
Schoeller, WolfgangUniBi;
Mattay, JochenUniBi
Einrichtung
Abstract / Bemerkung
The displacement processes of several guests, incorporated in a calixarene host system, were investigated in the gas phase by electrospray ionization-Fourier transform-ion cyclotron resonance (ESI-FT-ICR) mass spectrometry. The complexes resulting from a resorcin[4]arene host with ammonia and sec-butylamine guests were isolated in an ICR-cell, separately using both states of the photos-witch as well as two reference systems for the open and closed forms of the photoswitchable host. The isolated complexes were forced to exchange the guest by using methylamine, ethylamine and sec-butylamine, resulting in different reaction rates for all the measured systems. Especially, the reaction rates of both states of the photoswitch are dependent on the provided guest. Potential side effects like proton exchanges were examined by an H/D-exchange experiment. The results were investigated and supported by quantum chemical calculations (DFT). Copyright (C) 2008 John Wiley & Sons, Ltd.
Stichworte
photochemistry;
resorcin[4]arene;
electrospray mass spectrometry;
computational;
modeling;
DFT;
host-guest chemistry;
gas-phase ion chemistry
Erscheinungsjahr
2008
Zeitschriftentitel
Journal of Mass Spectrometry
Band
43
Ausgabe
11
Seite(n)
1553-1564
ISSN
1076-5174
eISSN
1096-9888
Page URI
https://pub.uni-bielefeld.de/record/1636725
Zitieren
Letzel M, Schäfer C, Novara FR, et al. A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene. Journal of Mass Spectrometry. 2008;43(11):1553-1564.
Letzel, M., Schäfer, C., Novara, F. R., Speranza, M., Rozhenko, A. B., Schoeller, W., & Mattay, J. (2008). A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene. Journal of Mass Spectrometry, 43(11), 1553-1564. https://doi.org/10.1002/jms.1464
Letzel, Matthias, Schäfer, Christian, Novara, Francesca R., Speranza, Maurizio, Rozhenko, Alexander B., Schoeller, Wolfgang, and Mattay, Jochen. 2008. “A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene”. Journal of Mass Spectrometry 43 (11): 1553-1564.
Letzel, M., Schäfer, C., Novara, F. R., Speranza, M., Rozhenko, A. B., Schoeller, W., and Mattay, J. (2008). A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene. Journal of Mass Spectrometry 43, 1553-1564.
Letzel, M., et al., 2008. A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene. Journal of Mass Spectrometry, 43(11), p 1553-1564.
M. Letzel, et al., “A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene”, Journal of Mass Spectrometry, vol. 43, 2008, pp. 1553-1564.
Letzel, M., Schäfer, C., Novara, F.R., Speranza, M., Rozhenko, A.B., Schoeller, W., Mattay, J.: A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene. Journal of Mass Spectrometry. 43, 1553-1564 (2008).
Letzel, Matthias, Schäfer, Christian, Novara, Francesca R., Speranza, Maurizio, Rozhenko, Alexander B., Schoeller, Wolfgang, and Mattay, Jochen. “A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene”. Journal of Mass Spectrometry 43.11 (2008): 1553-1564.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
4 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Optical switches with biplanemers obtained by intramolecular photocycloaddition reactions of tethered arenes.
Meier H, Cao D., Chem Soc Rev 42(1), 2013
PMID: 23032934
Meier H, Cao D., Chem Soc Rev 42(1), 2013
PMID: 23032934
A light controlled cavitand wall regulates guest binding.
Berryman OB, Sather AC, Rebek J., Chem Commun (Camb) 47(2), 2011
PMID: 21116523
Berryman OB, Sather AC, Rebek J., Chem Commun (Camb) 47(2), 2011
PMID: 21116523
Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study.
Botta B, Fraschetti C, Novara FR, Tafi A, Sacco F, Mannina L, Sobolev AP, Mattay J, Letzel MC, Speranza M., Org Biomol Chem 7(9), 2009
PMID: 19590774
Botta B, Fraschetti C, Novara FR, Tafi A, Sacco F, Mannina L, Sobolev AP, Mattay J, Letzel MC, Speranza M., Org Biomol Chem 7(9), 2009
PMID: 19590774
Photochromic resorcin[4]arenes: stabilization of intramolecular anthracene dimers in solution.
Schäfer C, Rozhenko AB, Mattay J., Photochem Photobiol Sci 8(8), 2009
PMID: 19639122
Schäfer C, Rozhenko AB, Mattay J., Photochem Photobiol Sci 8(8), 2009
PMID: 19639122
38 References
Daten bereitgestellt von Europe PubMed Central.
Resorcinarenes
Timmerman, Tetrahedron 52(), 1996
Timmerman, Tetrahedron 52(), 1996
Resorcinarenes
Sliwa, Polish Journal of Chemistry 77(), 2003
Sliwa, Polish Journal of Chemistry 77(), 2003
Unimolecular photochemistry of anthracenes
Becker, Chemical Reviews 93(), 1993
Becker, Chemical Reviews 93(), 1993
Photodimerization of anthracenes in fluid solution: structural aspects
Bouas-Laurent, Chemical Society Reviews 29(), 2000
Bouas-Laurent, Chemical Society Reviews 29(), 2000
Photodimerization of anthracenes in fluid solution: (part 2) mechanistic aspects of the photocycloaddition and of the photochemical and thermal cleavage
Bouas-Laurent, Chemical Society Reviews 30(), 2001
Bouas-Laurent, Chemical Society Reviews 30(), 2001
Light-responsive metal encapsulation in calix[4]arene
Deng, Chemistry Letters 21(), 1992
Deng, Chemistry Letters 21(), 1992
Light-switched ionophoric calix[4]arenes
Deng, Tetrahedron Letters 33(), 1992
Deng, Tetrahedron Letters 33(), 1992
Synthesis of two new n-heptanal and n-butylaldehyde resorcinarene derivatives bearing fluorescent anthracene residues
Zhang, Hecheng Huaxue 9(), 2001
Zhang, Hecheng Huaxue 9(), 2001
Preparation of photocyclizable dianthracene derivatives of resorc[4]arenes which are potential photoswitches
Schäfer, Photochemical and Photobiological Sciences 3(), 2004
Schäfer, Photochemical and Photobiological Sciences 3(), 2004
Photochemical single-molecule affinity switch.
Schafer C, Eckel R, Ros R, Mattay J, Anselmetti D., J. Am. Chem. Soc. 129(6), 2007
PMID: 17249675
Schafer C, Eckel R, Ros R, Mattay J, Anselmetti D., J. Am. Chem. Soc. 129(6), 2007
PMID: 17249675
Investigating molecular recognition with mass spectrometry: characterization of calixarene-based self-assembling capsule hosts with charged guests
Schalley, Journal of the American Chemical Society 121(), 1999
Schalley, Journal of the American Chemical Society 121(), 1999
Characterization of self-assembling encapsulation complexes in the gas phase and solution
Schalley, Journal of the American Chemical Society 121(), 1999
Schalley, Journal of the American Chemical Society 121(), 1999
Supramolecular chemistry goes gas phase: the mass spectrometric examination of noncovalent interactions in host-guest chemistry and molecular recognition
Schalley, International Journal of Mass Spectrometry 194(), 2000
Schalley, International Journal of Mass Spectrometry 194(), 2000
Host-guest complexes between calix[4]arenes derived from resorcinol and alkylammonium ions
Lippmann, Angewandte Chemie International Edition 32(), 1993
Lippmann, Angewandte Chemie International Edition 32(), 1993
Chiral recognition by resorcin[4]arene receptors: intrinsic kinetics and dynamics
Tafi, Chemistry- A European Journal 10(), 2004
Tafi, Chemistry- A European Journal 10(), 2004
Cavity effects on the enantioselectivity of chiral amido[4]resorcinarene stereoisomers
Botta, Angewandte Chemie International Edition 43(), 2004
Botta, Angewandte Chemie International Edition 43(), 2004
Flattened cone 2,8,14,20-tetrakis(L-valinamido)-[4]resorcinarene: an enantioselective allosteric receptor in the gas phase
Botta, Angewandte Chemie International Edition 45(), 2006
Botta, Angewandte Chemie International Edition 45(), 2006
Nanosecond flash studies of reduction of benzophenone by aliphatic amines. Quantum yields and kinetic isotope effects
Inbar, Journal of the American Chemical Society 103(), 1981
Inbar, Journal of the American Chemical Society 103(), 1981
Reactions of dihalobenzene radical cations with ammonia in the gas phase. Reactivity pattern for nucleophilic aromatic substitution
Thölmann, Journal of the American Chemical Society 113(), 1991
Thölmann, Journal of the American Chemical Society 113(), 1991
Parametrization of the ion-polar molecule collision rate constant by trajectory calculations
Su, Journal of Chemical Physics 66(), 1982
Su, Journal of Chemical Physics 66(), 1982
Trajectory calculations of ion-polar molecule capture rate constants at low temperatures
Su, Journal of Chemical Physics 88(), 1988
Su, Journal of Chemical Physics 88(), 1988
Erratum: trajectory calculations of ion-polar molecule capture rate constants at low temperatures [Journal of Chemical Physics 1988; 88: 4102]
Su, Journal of Chemical Physics 89(), 1988
Su, Journal of Chemical Physics 89(), 1988
Reliability of fourier transform-ion cyclotron resonance determinations of rate constants for ion/molecule reactions
Grover, European Mass Spectrometry 2(), 1996
Grover, European Mass Spectrometry 2(), 1996
Electronic structure calculations on workstation computers: the program system turbomole
Ahlrichs, Chemical Physics Letters 162(), 1989
Ahlrichs, Chemical Physics Letters 162(), 1989
Ahlrichs, 1995
On some approximations in applications of Xα theory
Dunlap, Journal of Chemical Physics 71(), 1979
Dunlap, Journal of Chemical Physics 71(), 1979
Integral approximations for LCAO-SCF calculations
Vahtras, Chemical Physics Letters 213(), 1993
Vahtras, Chemical Physics Letters 213(), 1993
Auxiliary basis sets to approximate Coulomb potentials
Eichkorn, Chemical Physics Letters 240(), 1995
Eichkorn, Chemical Physics Letters 240(), 1995
Density-functional exchange-energy approximation with correct asymptotic behavior.
Becke AD., Phys Rev A Gen Phys 38(6), 1988
PMID: 9900728
Becke AD., Phys Rev A Gen Phys 38(6), 1988
PMID: 9900728
Density-functional approximation for the correlation energy of the inhomogeneous electron gas.
Perdew JP., Phys. Rev., B Condens. Matter 33(12), 1986
PMID: 9938299
Perdew JP., Phys. Rev., B Condens. Matter 33(12), 1986
PMID: 9938299
Fully optimized contracted Gaussian basis sets for atoms Li to Kr
Schaefer, Journal of Chemical Physics 97(), 1992
Schaefer, Journal of Chemical Physics 97(), 1992
Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr
Schaefer, Journal of Chemical Physics 100(), 1994
Schaefer, Journal of Chemical Physics 100(), 1994
VMD: visual molecular dynamics.
Humphrey W, Dalke A, Schulten K., J Mol Graph 14(1), 1996
PMID: 8744570
Humphrey W, Dalke A, Schulten K., J Mol Graph 14(1), 1996
PMID: 8744570
AUTHOR UNKNOWN, 1969
Evaluated gas phase basicities and proton affinities of molecules: an update
Hunter, Journal of Physical and Chemical Reference Data 27(), 1998
Hunter, Journal of Physical and Chemical Reference Data 27(), 1998
Calixarenes as hosts for ammonium cations: a quantum chemical study and mass-spectrometric investigations
Schoeller, Chemistry- A European Journal 12(), 2006
Schoeller, Chemistry- A European Journal 12(), 2006
A density functional study of van der Waals interactions
Kamiya, Journal of Chemical Physics 117(), 2002
Kamiya, Journal of Chemical Physics 117(), 2002
Conformational features of calix[4]arenes with alkali metal cations: a quantum chemical investigation with density functional theory
Rozhenko, Journal of Molecular Structure (THEOCHEM) 732(), 2005
Rozhenko, Journal of Molecular Structure (THEOCHEM) 732(), 2005
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