Abstract
Alcohol complexation properties of eight mono- and diphenyl phosphonate-bridged cavitands (Scheme 1). were studied by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI-FTICR) and theoretical calculations. The cavitands varied in number and position of phenyl phosphonate bridges and their orientation with respect to the cavity, length of the lower rim alkyl chains, and substituents at apical positions of the resorcarene skeleton. The specificities of the different cavitands toward primary, secondary, and tertiary alcohols varying long of the alkyl chain were investigated, together with the stabilities of the formed complexes. The number, position, and orientation of the P=O moieties affected the complex formation of the cavitands and stability of the complexes dramatically. Methyl groups at apical positions of the resorcarene skeleton also affected the complexation properties. Although length and branching of the alkyl chain of the alcohol influenced the complex formation, the effect on stability of the complexes was negligible.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Moran, J. R.; Karbach, S.; Cram, D. J. Cavitands: Synthetic Molecular Vessels. J. Am. Chem. Soc. 1982, 104, 5826–5828.
Rudkevich, D. M.; Rebek, J., Jr. Deepening Cavitands. Eur. J. Org. Chem. 1999, 1991–2005.
Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; RSC: Cambridge, 1994; p 85.
Cram, D. J.; Karbach, S.; Kim, H.-E.; Knobler, C. B.; Maverick, E. F.; Ericson, J. L.; Helgeson, R. C. Host-Guest Complexation. 46. Cavitands as Open Molecular Vessels Form Solvates. J. Am. Chem. Soc. 1988, 110, 2229–2237.
Cram, D. J.; Stewart, K. D.; Goldberg, I.; Trueblood, K. N. Complementary Solutes Enter Nonpolar Preorganized Cavities in Lipophilic Noncomplementary Media. J. Am. Chem. Soc. 1985, 107, 2574–2575.
Tucker, J. A.; Knobler, C. B.; Trueblood, K. N.; Cram, D. J. Host-Guest Complexation. 49. Cavitands Containing Two Binding Cavities. J. Am. Chem. Soc. 1989, 111, 3688–3699.
Moran, J. R.; Ericson, J. L.; Dalcanale, E.; Bryant, J. A.; Knobler, C. B.; Cram, D. J. Vases and Kites as Cavitands. J. Am. Chem. Soc. 1991, 113, 5707–5714.
Cram, D. J.; Choi, H.-J.; Bryant, J. A.; Knobler, C. B. Solvophobic and Entropic Driving Forces for Forming Velcraplexes, Which are Four-Fold, Lock-Key Dimers in Organic Media. J. Am. Chem. Soc. 1992, 114, 7748–7765.
Lippmann, T.; Wilde, H.; Dalcanale, E.; Mavilla, L.; Mann, G.; Heyer, U.; Spera, S. Synthesis and Configurational Analysis of a Novel Class of Cavitands Containing Four Dioxaphosphocin Moieties. J. Org. Chem. 1995, 60, 235–242.
Dalcanale, E.; Jacopozzi, P.; Ugozolli, F.; Mann, G. Synthesis and Configurational Analysis of Mixed-Bridged Phosphonate Cavitands. Supramol. Chem. 1998, 9, 305–316.
Pinalli, R.; Suman, M.; Dalcanale, E. Cavitands at Work: From Molecular Recognition to Supramolecular Sensors. Eur. J. Org. Chem. 2004, 451–462.
Nelli, P.; Dalcanale, E.; Faglia, G.; Sberveglieri, G.; Soncini, P. Cavitands as Selective Materials for QMB Sensors for Nitrobenzene and Other Aromatic Vapors. Sens. Actuators B 1993, 13/14, 302–304.
Hartmann, J.; Auge, J.; Lucklum, R.; Rösler, S.; Hauptmann, P.; Adler, B.; Dalcanale, E. Supramolecular Interactions on Mass Sensitive Sensors in Gas-Phases and Liquids. Sens. Actuators B 1996, 34, 305–311.
Hartmann, J.; Hauptmann, P.; Levi, S.; Dalcanale, E. Chemical Sensing with Cavitands: Influence of Cavity Shape and Dimensions on the Detection of Solvent Vapors. Sens. Actuators B 1996, 35/36, 154–157.
Ferrari, M.; Ferrari, V.; Marioli, D.; Taroni, A.; Suman, M.; Dalcanale, E. Cavitand-Coated PZT Resonant Piezo-Layer Sensors: Properties, Structure, and Comparison with QCM Sensors at Different Temperatures under Exposure to Organic Vapors. Sens. Actuators B 2004, 103, 240–246.
Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Supramolecular Sensors for the Detection of Alcohols. Angew. Chem. Int. Ed. 1999, 38, 2377–2380.
Suman, M.; Freddi, M.; Massera, C.; Ugozzoli, F.; Dalcanale, E. Rational Design of Cavitand Receptors for Mass Sensors. J. Am. Chem. Soc. 2003, 125, 12068–12069.
Suman, M.; Bouzouane, N.; Barbieri, E.; Ugozzoli, F.; Dalcanale, E. Cavitand-Based Supramolecular Sensors for the Detection of Acetates. J. Supramol. Chem. 2002, 2, 97–106.
Yamashita, M.; Fenn, J. B. Electrospray Ion Source. Another Variation on the Free-Jet Theme. J. Phys. Chem. 1984, 88, 4451–4459.
Fenn, J. B.; Mann, M.; Meng, K. C.; Wong, S. F.; Whitehouse, C. M. Electrospray Ionization for Mass Spectrometry of Large Biomolecules. Science 1989, 246, 64–70.
Cole, R. B., Ed. In Electrospray Ionization Mass Spectrometry; Wiley: New York, 1997.
Bruins, A. P. Mechanistic Aspects of Electrospray Ionization. J. Chromatogr. A 1998, 794, 345–357.
Schalley, C. A. Molecular Recognition and Supramolecular Chemistry in the Gas Phase. Mass Spectrom. Rev. 2001, 20, 253–309.
Dearden, D. V.; Liang, Y.; Nicoll, J. B.; Kellersberger, K. A. Study of Gas-Phase Molecular Recognition Using Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. J. Mass Spectrom. 2001, 36, 989–997.
Brodbelt, J. S. Probing Molecular Recognition by Mass Spectrometry. Int. J. Mass Spectrom. 2000, 200, 57–69.
Schalley, C. A. Supramolecular Chemistry Goes Gas Phase: The Mass Spectrometric Examination of Noncovalent Interactions in Host-Guest Chemistry and Molecular Recognition. Int. J. Mass Spectrom. 2000, 194, 11–39.
Daniel, J. M.; Friess, S. D.; Rajagopalan, S.; Wendt, S.; Zenobi, R. Quantitative Determination of Noncovalent Binding Interactions Using Soft Ionization Mass Spectrometry. Int. J. Mass Spectrom. 2002, 216, 1–27.
Vincenti, M.; Irico, A.; Dalcanale, E. 1998; Host-Guest Interactions in Mass Spectrometry. Karjalainen, E. J.; Hesso, A. E.; Jalonen, J.; Karjalainen, U. P., Ed.; In Advances in Mass Spectrometry; pp 129–150. Elsevier: Amsterdam.
Vincenti, M.; Dalcanale, E.; Soncini, P.; Guglielmetti, G. Host-Guest Complexation in the Gas Phase by Desorption Chemical Ionization Mass Spectrometry. J. Am. Chem. Soc. 1990, 112, 445–447.
Vincenti, M.; Dalcanale, E. Host-Guest Complexation in the Gas Phase. Investigation of the Mechanism of Interaction between Cavitands and Neutral Guest Molecules. J. Chem. Soc. Perkin Trans. 1995, 2, 1069–1076.
Nuutinen, J. M. J.; Irico, A.; Vincenti, M.; Dalcanale, E.; Pakarinen, J. M. H.; Vainiotalo, P. Gas-Phase Ion-Molecule Reactions between a Series of Protonated Diastereomeric Cavitands and Neutral Amines Studied by ESI-FTICRMS: Gas-Phase Inclusion Complex Formation. J. Am. Chem. Soc. 2000, 122, 10090–10100.
Irico, A.; Vincenti, M.; Dalcanale, E. Diastereoselective Formation of Host-Guest Complexes Between a Series of Phosphonate-Bridged Cavitands and Alkyl- and Arylammonium Ions Studied by Liquid Secondary-Ion Mass Spectrometry. Chem. Eur. J. 2001, 7(2034), 2042.
Vincenti, M.; Irico, A. Gas-Phase Interactions of Calixarene- and Resorcinarene-Cavitands with Molecular Guests Studied by Mass Spectrometry. Int. J. Mass Spectrom. 2002, 214, 23–36.
Woodget, B. W.; Cooper, D. Samples and Standards; Wiley: Chichester, 1987; 40–47.
Hamilton, L. F.; Simpson, S. G.; Ellis, D. W. Calculations of Analytical Chemistry; McGraw-Hill: New York, 1960; 2–11.
McGormick, D.; Roach, A. Measurements, Statistics, and Computation; Wiley: Chichester, 1987; 24–31.
de Koning, L. J.; Nibbering, N. M. M.; van Orden, S. L.; Laukien, F. H. Mass Selection of Ions in a Fourier Transform Ion Cyclotron Resonance Trap Using Correlated Harmonic Excitation Fields (CHEF). Int. J. Mass Spectrom. Ion Processes 1997, 165/166, 209–219.
Hop, C. E. C. A.; McMahon, T. B.; Willett, G. D. Determination of Bond Dissociation Energies via Energy-Resolved Collision Induced Dissociation in a Fourier Transform Ion Cyclotron Resonance Spectrometer. Int. J. Mass Spectrom. Ion Processes 1990, 101, 191–208.
Sievers, H. L.; Grützmacher, H.-F.; Caravatti, P. The Geometrical Factor of Infinitely Long Cylindrical ICR Cells for Collision Energy-Resolved Mass Spectrometry: Appearance Energies of EI +2 (E=P, As, Sb, and Bi) from Collision-Induced Dissociation of EI +3 and [EI2 · ligand]+ Complexes. Int. J. Mass Spectrom. Ion Processes 1996, 157/158, 233–247.
Heeren, R. M. A.; Vekey, K. A Novel Method to Determine Collisional Energy Transfer Efficiency by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. Rabid Commun. Mass Spectrom. 1998, 12, 1175–1181.
Jacopozzi, P.; Dalcanale, E.; Spera, S.; Chrisstoffels, L. A. J.; Reinhoudt, D.N.; Lippmann, T.; Mann, G. Synthesis and Configurational Analysis of Phosphonate Cavitands. J. Chem. Soc. Perkin Trans. 2 1998, 3, 671–677.
Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. Linear Solvation Energy Relationships. 23. A Comprehensive Collection of the Solvatochromic Parameters, π*, α, and β, and Some Methods for Simplifying the Generalized Solvatochromic Equation. J. Org. Chem. 1983, 48, 2877–2887.
Gonçalves, R. M. C.; Simoes, A. M. N.; Albuquerque, L. M. P. C.; Roses, M. ; Rafols, C.; Bosch, E. Kamlet-Taft Solvatochromic Parameters for Hydroxylic Solvents. J. Chem. Res. Synop. 1993, 214–215.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published online January 18, 2006
Rights and permissions
About this article
Cite this article
Ventola, E., Vainiotalo, P., Suman, M. et al. ESI-FTICR mass spectrometric study of alcohol complexation properties of mono- and diphosphonate-bridged cavitands. The official journal of The American Society for Mass Spectrometry 17, 213–221 (2006). https://doi.org/10.1016/j.jasms.2005.10.017
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1016/j.jasms.2005.10.017