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Volumn 23, Issue 10, 2012, Pages 1786-1793

Unusual complex formation and chemical reaction of haloacetate anion on the exterior surface of cucurbit[6]uril in the gas phase

Author keywords

Anionic complex; CB 6 ; Cucurbit 6 uril; Electrospray ionization; Halide; Haloacetate; Intramolecular SN2 reaction; Ion mobility spectrometry

Indexed keywords

ANIONIC COMPLEX; CB[6]; CUCURBIT[6]URIL; HALIDE; HALOACETATE; INTRAMOLECULAR SN2 REACTION; ION MOBILITY SPECTROMETRY;

EID: 84868254692     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-012-0443-6     Document Type: Article
Times cited : (17)

References (49)
  • 2
    • 0041472445 scopus 로고    scopus 로고
    • Cucurbituril homologues and derivatives: New opportunities in supramolecular chemistry
    • Lee, J.W., Samal, S., Selvapalam, N., Kim, H.J., Kim, K.: Cucurbituril Homologues and Derivatives: New Opportunities in Supramolecular Chemistry. Acc. Chem. Res. 36, 621-630 (2003)
    • (2003) Acc. Chem. Res. , vol.36 , pp. 621-630
    • Lee, J.W.1    Samal, S.2    Selvapalam, N.3    Kim, H.J.4    Kim, K.5
  • 6
    • 0031929934 scopus 로고    scopus 로고
    • A molecular bowl with metal ion as bottom: Reversible inclusion of organic molecules in cesium ion complexed cucurbituril
    • Whang, D., Heo, J., Park, J.H., Kim, K.: A Molecular Bowl with Metal Ion as Bottom: Reversible Inclusion of Organic Molecules in Cesium Ion Complexed Cucurbituril. Angew. Chem. Int. Ed. 37, 78-80 (1998)
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 78-80
    • Whang, D.1    Heo, J.2    Park, J.H.3    Kim, K.4
  • 7
    • 33947500664 scopus 로고    scopus 로고
    • Supramolecular assemblies built with host-stabilized charge-transfer interactions
    • Ko, Y.H., Kim, E., Hwang, I., Kim, K.: Supramolecular Assemblies Built with Host-Stabilized Charge-Transfer Interactions. Chem. Commun. 1305-1315 (2007)
    • (2007) Chem. Commun. , pp. 1305-1315
    • Ko, Y.H.1    Kim, E.2    Hwang, I.3    Kim, K.4
  • 8
    • 0035983123 scopus 로고    scopus 로고
    • Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies
    • Kim, K.: Mechanically Interlocked Molecules Incorporating Cucurbituril and Their Supramolecular Assemblies. Chem. Soc. Rev. 31, 96-107 (2002)
    • (2002) Chem. Soc. Rev. , vol.31 , pp. 96-107
    • Kim, K.1
  • 9
    • 0036860738 scopus 로고    scopus 로고
    • Self-assembled ternary complex of cationic dendrimer, cucurbituril, and DNA: Noncovalent strategy in developing a gene delivery carrier
    • Lim, Y.B., Kim, T., Lee, J.W., Kim, S.M., Kim, H.J., Kim, K., Park, J.S.: Self-Assembled Ternary Complex of Cationic Dendrimer, Cucurbituril, and DNA: Noncovalent Strategy in Developing a Gene Delivery Carrier. Bioconjugate Chem. 13, 1181-1185 (2002)
    • (2002) Bioconjugate Chem. , vol.13 , pp. 1181-1185
    • Lim, Y.B.1    Kim, T.2    Lee, J.W.3    Kim, S.M.4    Kim, H.J.5    Kim, K.6    Park, J.S.7
  • 10
    • 74549142011 scopus 로고    scopus 로고
    • Galactosylated cucurbituril-inclusion polyplex for hepatocyte-targeted gene delivery
    • Kim, S.K., Park, K.M., Singha, K., Kim, J., Ahn, Y., Kim, K., Kim, W.J.: Galactosylated Cucurbituril-Inclusion Polyplex for Hepatocyte-Targeted Gene Delivery. Chem. Commun. 46, 692-694 (2010)
    • (2010) Chem. Commun. , vol.46 , pp. 692-694
    • Kim, S.K.1    Park, K.M.2    Singha, K.3    Kim, J.4    Ahn, Y.5    Kim, K.6    Kim, W.J.7
  • 11
    • 77954304412 scopus 로고    scopus 로고
    • Reduction-sensitive, robust vesicles with a noncovalently modifiable surface as a multifunctional drug-delivery platform
    • Park, K.M., Lee, D.-W., Sarkar, B., Jung, H., Kim, J., Ko, Y.H., Lee, K.E., Jeon, H., Kim, K.: Reduction-Sensitive, Robust Vesicles with a Noncovalently Modifiable Surface as a Multifunctional Drug-Delivery Platform. Small 6, 1430-1441 (2010)
    • (2010) Small , vol.6 , pp. 1430-1441
    • Park, K.M.1    Lee, D.-W.2    Sarkar, B.3    Jung, H.4    Kim, J.5    Ko, Y.H.6    Lee, K.E.7    Jeon, H.8    Kim, K.9
  • 12
    • 26844563376 scopus 로고    scopus 로고
    • Charge-mediated recognition of N-terminal tryptophan in aqueous solution by a synthetic host
    • Bush, M.E., Bouley, N.D., Urbach, A.R.: Charge-Mediated Recognition of N-Terminal Tryptophan in Aqueous Solution by a Synthetic Host. J. Am. Chem. Soc. 127, 14511-14517 (2005)
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 14511-14517
    • Bush, M.E.1    Bouley, N.D.2    Urbach, A.R.3
  • 13
    • 67749119980 scopus 로고    scopus 로고
    • Multivalent recognition of peptides by modular self-assembled receptors
    • Reczek, J.J., Kennedy, A.A., Halbert, B.T., Urbach, A.R.: Multivalent Recognition of Peptides by Modular Self-Assembled Receptors. J. Am. Chem. Soc. 131, 2408-2415 (2009)
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 2408-2415
    • Reczek, J.J.1    Kennedy, A.A.2    Halbert, B.T.3    Urbach, A.R.4
  • 14
    • 79957542898 scopus 로고    scopus 로고
    • Molecular recognition of amino acids, peptides, and proteins by cucurbit[n]uril receptors
    • Urbach, A.R., Ramalingam, V.: Molecular Recognition of Amino Acids, Peptides, and Proteins by Cucurbit[n]uril Receptors. Israel J. Chem. 51, 664-678 (2011)
    • (2011) Israel J. Chem. , vol.51 , pp. 664-678
    • Urbach, A.R.1    Ramalingam, V.2
  • 17
    • 33751305203 scopus 로고    scopus 로고
    • Molecular capsules based on cucurbit[5]uril encapsulating "naked" anion chlorine
    • Liu, J.X., Long, L.S., Huang, R.B., Zheng, L.S.: Molecular Capsules Based on Cucurbit[5]uril Encapsulating "Naked" Anion Chlorine. Cryst. Growth Des. 6, 2611-2614 (2006)
    • (2006) Cryst. Growth Des. , vol.6 , pp. 2611-2614
    • Liu, J.X.1    Long, L.S.2    Huang, R.B.3    Zheng, L.S.4
  • 18
    • 37249052752 scopus 로고    scopus 로고
    • Interesting anion-inclusion behavior of cucurbit[5]uril and its lanthanide-capped molecular capsule
    • Liu, J.X., Long, L.S., Huang, R.B., Zheng, L.S.: Interesting Anion-Inclusion Behavior of Cucurbit[5]uril and Its Lanthanide-Capped Molecular Capsule. Inorg. Chem. 46, 10168-10173 (2007)
    • (2007) Inorg. Chem. , vol.46 , pp. 10168-10173
    • Liu, J.X.1    Long, L.S.2    Huang, R.B.3    Zheng, L.S.4
  • 19
    • 0033802014 scopus 로고    scopus 로고
    • Supramolecular chemistry goes gas phase: The mass spectrometric examination of noncovalent interactions in host-guest chemistry and molecular recognition
    • 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. 194, 11-39 (2000)
    • (2000) Int. J. Mass Spectrom. , vol.194 , pp. 11-39
    • Schalley, C.A.1
  • 20
    • 34447561942 scopus 로고    scopus 로고
    • Molecular beads on a charged molecular string: α,ω- alkyldiammonium complexes of cucurbit[6]uril in the gas phase
    • Zhang, H., Ferrell, T.A., Asplund, M.C., Dearden, D.V.: Molecular Beads on a Charged Molecular String: α,ω-Alkyldiammonium Complexes of Cucurbit[6]uril in the Gas Phase. Int. J. Mass Spectrom. 265, 187-196 (2007)
    • (2007) Int. J. Mass Spectrom. , vol.265 , pp. 187-196
    • Zhang, H.1    Ferrell, T.A.2    Asplund, M.C.3    Dearden, D.V.4
  • 21
    • 0041708011 scopus 로고    scopus 로고
    • Cucurbit[6]uril pseudorotaxanes: Distinctive gas-phase dissociation and reactivity
    • Zhang, H., Paulsen, E.S., Walker, K.A., Krakowiak, K.E., Dearden, D.V.: Cucurbit[6]uril Pseudorotaxanes: Distinctive Gas-Phase Dissociation and Reactivity. J. Am. Chem. Soc. 125, 9284-9285 (2003)
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 9284-9285
    • Zhang, H.1    Paulsen, E.S.2    Walker, K.A.3    Krakowiak, K.E.4    Dearden, D.V.5
  • 22
    • 61649115229 scopus 로고    scopus 로고
    • One ring to bind them all: Shape-selective complexation of phenylenediamine isomers with cucurbit[6]uril in the gas phase
    • Dearden, D.V., Ferrell, T.A., Asplund, M.C., Zilch, L.W., Julian, R.R., Jarrold, M.F.: One Ring to Bind Them All: Shape-Selective Complexation of Phenylenediamine Isomers with Cucurbit[6]uril in the Gas Phase. J. Phys. Chem. A 113, 989-997 (2009)
    • (2009) J. Phys. Chem. A , vol.113 , pp. 989-997
    • Dearden, D.V.1    Ferrell, T.A.2    Asplund, M.C.3    Zilch, L.W.4    Julian, R.R.5    Jarrold, M.F.6
  • 23
    • 63849305221 scopus 로고    scopus 로고
    • Supramolecular modification of ion chemistry: Modulation of peptide charge state and dissociation behavior through complexation with cucurbit[n]uril (N=5, 6) or α-cyclodextrin
    • Zhang, H., Grabenauer, M., Bowers, M.T., Dearden, D.V.: Supramolecular Modification of Ion Chemistry: Modulation of Peptide Charge State and Dissociation Behavior through Complexation with Cucurbit[n]uril (N=5, 6) or α-Cyclodextrin. J. Phys. Chem. A 113, 1508-1517 (2009)
    • (2009) J. Phys. Chem. A , vol.113 , pp. 1508-1517
    • Zhang, H.1    Grabenauer, M.2    Bowers, M.T.3    Dearden, D.V.4
  • 24
    • 58849097982 scopus 로고    scopus 로고
    • Discrete, multi-component complexes with cucurbit[8]uril in the gas-phase
    • Deroo, S., Rauwald, U., Robinson, C.V., Scherman, O.A.: Discrete, Multi-Component Complexes with Cucurbit[8]uril in the Gas-Phase. Chem. Commun. 644-646 (2009)
    • (2009) Chem. Commun. , pp. 644-646
    • Deroo, S.1    Rauwald, U.2    Robinson, C.V.3    Scherman, O.A.4
  • 25
    • 77954343436 scopus 로고    scopus 로고
    • Correlating solution binding and esi-ms stabilities by incorporating solvation effects in a confined cucurbit[8]uril system
    • Rauwald, U., Biedermann, F., Deroo, S., Robinson, C.V., Scherman, O.A.: Correlating Solution Binding and Esi-Ms Stabilities by Incorporating Solvation Effects in a Confined Cucurbit[8]uril System. J. Phys. Chem. B 114, 8606-8615 (2010)
    • (2010) J. Phys. Chem. B , vol.114 , pp. 8606-8615
    • Rauwald, U.1    Biedermann, F.2    Deroo, S.3    Robinson, C.V.4    Scherman, O.A.5
  • 27
    • 0037075426 scopus 로고    scopus 로고
    • Nanocrystalline aggregation of serine detected by electrospray ionization mass spectrometry: Origin of the stable homochiral GasPhase serine octamer
    • Julian, R.R., Hodyss, R., Kinnear, B., Jarrold, M.F., Beauchamp, J.L.: Nanocrystalline Aggregation of Serine Detected by Electrospray Ionization Mass Spectrometry: Origin of the Stable Homochiral GasPhase Serine Octamer. J. Phys. Chem. B 106, 1219-1228 (2002)
    • (2002) J. Phys. Chem. B , vol.106 , pp. 1219-1228
    • Julian, R.R.1    Hodyss, R.2    Kinnear, B.3    Jarrold, M.F.4    Beauchamp, J.L.5
  • 28
    • 0035975462 scopus 로고    scopus 로고
    • Magic number clusters of serine in the gas phase
    • Counterman, A.E., Clemmer, D.E.: Magic Number Clusters of Serine in the Gas Phase. J. Phys. Chem. B 105, 8092-8096 (2001)
    • (2001) J. Phys. Chem. B , vol.105 , pp. 8092-8096
    • Counterman, A.E.1    Clemmer, D.E.2
  • 29
    • 80054684751 scopus 로고    scopus 로고
    • Host-guest chemistry in the gas phase: Selected fragmentations of CB[6]-peptide complexes at lysine residues and its utility to probe the structures of small proteins
    • Heo, S.W., Choi, T.S., Park, K.M., Ko, Y.H., Kim, S.B., Kim, K., Kim, H.I.: Host-Guest Chemistry in the Gas Phase: Selected Fragmentations of CB[6]-Peptide Complexes at Lysine Residues and Its Utility to Probe the Structures of Small Proteins. Anal. Chem. 83, 7916-7923 (2011)
    • (2011) Anal. Chem. , vol.83 , pp. 7916-7923
    • Heo, S.W.1    Choi, T.S.2    Park, K.M.3    Ko, Y.H.4    Kim, S.B.5    Kim, K.6    Kim, H.I.7
  • 30
    • 83455201731 scopus 로고    scopus 로고
    • Host-guest chemistry in the gas phase: Complex formation with 18-crown-6 enhances helicity of alanine-based peptides
    • Ko, J.Y., Heo, S.W., Lee, J.H., Oh, H.B., Kim, H., Kim, H.I.: Host- Guest Chemistry in the Gas Phase: Complex Formation with 18-Crown-6 Enhances Helicity of Alanine-Based Peptides. J. Phys. Chem. A 115, 14215-14220 (2011)
    • (2011) J. Phys. Chem. A , vol.115 , pp. 14215-14220
    • Ko, J.Y.1    Heo, S.W.2    Lee, J.H.3    Oh, H.B.4    Kim, H.5    Kim, H.I.6
  • 31
    • 0035065837 scopus 로고    scopus 로고
    • Metabolism, microflora effects, and genotoxicity in haloacetic acid-treated cultures of rat cecal microbiota
    • Nelson, G.M., Swank, A.E., Brooks, L.R., Bailey, K.C., George, S.E.: Metabolism, Microflora Effects, and Genotoxicity in Haloacetic Acid-Treated Cultures of Rat Cecal Microbiota. Toxicol. Sci. 60, 232-241 (2001)
    • (2001) Toxicol. Sci. , vol.60 , pp. 232-241
    • Nelson, G.M.1    Swank, A.E.2    Brooks, L.R.3    Bailey, K.C.4    George, S.E.5
  • 32
    • 79959895173 scopus 로고    scopus 로고
    • Biological mechanism for the toxicity of haloacetic acid drinking water disinfection byproducts
    • Pals, J.A., Ang, J.K., Wagner, E.D., Plewa, M.J.: Biological Mechanism for the Toxicity of Haloacetic Acid Drinking Water Disinfection Byproducts. Environ. Sci. Technol. 45, 5791-5797 (2011)
    • (2011) Environ. Sci. Technol. , vol.45 , pp. 5791-5797
    • Pals, J.A.1    Ang, J.K.2    Wagner, E.D.3    Plewa, M.J.4
  • 33
    • 58149477901 scopus 로고    scopus 로고
    • Characterization of phosphorylated peptides using traveling wave-based and drift cell ion mobility mass spectrometry
    • Thalassinos, K., Grabenauer, M., Slade, S.E., Hilton, G.R., Bowers, M.T., Scrivens, J.H.: Characterization of Phosphorylated Peptides Using Traveling Wave-Based and Drift Cell Ion Mobility Mass Spectrometry. Anal. Chem. 81, 248-254 (2009)
    • (2009) Anal. Chem. , vol.81 , pp. 248-254
    • Thalassinos, K.1    Grabenauer, M.2    Slade, S.E.3    Hilton, G.R.4    Bowers, M.T.5    Scrivens, J.H.6
  • 34
    • 0033473749 scopus 로고    scopus 로고
    • A database of 660 peptide ion cross sections: Use of intrinsic size parameters for bona fide predictions of cross sections
    • Valentine, S.J., Counterman, A.E., Clemmer, D.E.: A Database of 660 Peptide Ion Cross Sections: Use of Intrinsic Size Parameters for Bona Fide Predictions of Cross Sections. J. Am. Soc. Mass Spectrom. 10, 1188-1211 (1999)
    • (1999) J. Am. Soc. Mass Spectrom. , vol.10 , pp. 1188-1211
    • Valentine, S.J.1    Counterman, A.E.2    Clemmer, D.E.3
  • 36
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. 3. The role of exact exchange
    • Becke, A.D.: Density-Functional Thermochemistry. 3. The Role of Exact Exchange. J. Chem. Phys. 98, 5648-5652 (1993)
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 38
    • 0345491105 scopus 로고
    • Development of the colle-salvetti correlation-energy formula into a functional of the electron-density
    • Lee, C.T., Yang, W.T., Parr, R.G.: Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron-Density. Phys. Rev. B 37, 785-789 (1988)
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.T.1    Yang, W.T.2    Parr, R.G.3
  • 39
    • 49649133169 scopus 로고
    • Effect of d-functions on molecular orbital energies for hydrocarbons
    • Harihara. Pc, Pople, J.A.: Effect of d-Functions on Molecular Orbital Energies for Hydrocarbons. Chem. Phys. Lett. 16, 217 (1972)
    • (1972) Chem. Phys. Lett. , vol.16 , pp. 217
    • Harihara, P.C.1    Pople, J.A.2
  • 42
    • 0000990198 scopus 로고    scopus 로고
    • Ab initio theoretical investigation of the mechanism for α-lactone formation from α-halocarboxylates: Leaving group, substituent, solvent, and isotope effects
    • Rodriquez, C.F., Williams, I.H.: Ab Initio Theoretical Investigation of the Mechanism for α-Lactone Formation from α-Halocarboxylates: Leaving Group, Substituent, Solvent, and Isotope Effects. J. Chem. Soc. Perkin Trans. 2, 959-965 (1997)
    • (1997) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 959-965
    • Rodriquez, C.F.1    Williams, I.H.2
  • 44
    • 0000359957 scopus 로고
    • Theoretical study of α-lactone, acetoxyl diradical, and the gas-phase dissociation of the chloracetate anion
    • Antolovic, D., Shiner, V.J., Davidson, E.R.: Theoretical Study of α-Lactone, Acetoxyl Diradical, and the Gas-Phase Dissociation of the Chloracetate Anion. J. Am. Chem. Soc. 110, 1375-1381 (1988)
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1375-1381
    • Antolovic, D.1    Shiner, V.J.2    Davidson, E.R.3
  • 45
    • 0000539225 scopus 로고
    • Collisional activation of intramolecular nucleophilic displacement reactions: The formation of acetolactone from dissociation of α-haloacetate negative ions
    • Graul, S.T., Squires, R.R.: Collisional Activation of Intramolecular Nucleophilic Displacement Reactions: The Formation of Acetolactone from Dissociation of α-Haloacetate Negative Ions. Int. J. Mass Spectrom. Ion Processes 100, 785-802 (1990)
    • (1990) Int. J. Mass Spectrom. Ion Processes , vol.100 , pp. 785-802
    • Graul, S.T.1    Squires, R.R.2
  • 46
    • 0001157243 scopus 로고
    • Bond energies and polarities1
    • Huggins, M.L.: Bond Energies and Polarities1. J. Am. Chem. Soc. 75, 4123-4126 (1953)
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 4123-4126
    • Huggins, M.L.1
  • 47
    • 15744384369 scopus 로고    scopus 로고
    • Cluster-phase reactions: GasPhase phosphorylation of peptides and model compounds with triphosphate anions
    • Cox, H.A., Hodyss, R., Beauchamp, J.L.: Cluster-Phase Reactions: GasPhase Phosphorylation of Peptides and Model Compounds with Triphosphate Anions. J. Am. Chem. Soc. 127, 4084-4090 (2005)
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 4084-4090
    • Cox, H.A.1    Hodyss, R.2    Beauchamp, J.L.3
  • 48
    • 34547332614 scopus 로고    scopus 로고
    • Cluster phase chemistry: Collisions of vibrationally excited cationic dicarboxylic acid clusters with water molecules initiate dissociation of cluster components
    • Kim, H.I., Beauchamp, J.L.: Cluster Phase Chemistry: Collisions of Vibrationally Excited Cationic Dicarboxylic Acid Clusters with Water Molecules Initiate Dissociation of Cluster Components. J. Phys. Chem. A 111, 5954-5967 (2007)
    • (2007) J. Phys. Chem. A , vol.111 , pp. 5954-5967
    • Kim, H.I.1    Beauchamp, J.L.2
  • 49
    • 33746422944 scopus 로고    scopus 로고
    • Cluster phase chemistry: Gas phase reactions of anionic sodium salts of dicarboxylic acid clusters with water molecules
    • Kim, H.I., Goddard, W.A., Beauchamp, J.L.: Cluster Phase Chemistry: Gas Phase Reactions of Anionic Sodium Salts of Dicarboxylic Acid Clusters with Water Molecules. J. Phys. Chem. A 110, 7777-7786 (2006)
    • (2006) J. Phys. Chem. A , vol.110 , pp. 7777-7786
    • Kim, H.I.1    Goddard, W.A.2    Beauchamp, J.L.3


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