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Volumn 39, Issue 8, 2004, Pages 930-941

Gas-phase acidity of D-glucose. A density functional theory study

Author keywords

D glucose; Density functional theory calculations; Gas phase acidity; Mutarotation; Ring opening process

Indexed keywords

ANOMERS; DEPROTONATION; GAS-PHASE ACIDITY; INTERCONVERSIONS;

EID: 4444306253     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.671     Document Type: Article
Times cited : (33)

References (46)
  • 2
    • 84990704698 scopus 로고
    • Structural memory effects influencing decompositions of glucose alkoxide anions produced from monoterpene glycoside isomers in tandem mass spectrometry
    • Cole RB, Tabet JC, Salles C, Jallageas JC, Crouzet J. Structural memory effects influencing decompositions of glucose alkoxide anions produced from monoterpene glycoside isomers in tandem mass spectrometry. Rapid Commun. Mass Spectrom. 1989; 3: 59.
    • (1989) Rapid Commun. Mass Spectrom. , vol.3 , pp. 59
    • Cole, R.B.1    Tabet, J.C.2    Salles, C.3    Jallageas, J.C.4    Crouzet, J.5
  • 3
    • 0021106251 scopus 로고
    • Fast-atom-bombardment, negative-ion mass spectrometry of the mycobacterial O-methyl-D-glucose polysaccharide and lipopolysaccharides
    • Dell A, Ballou CE. Fast-atom-bombardment, negative-ion mass spectrometry of the mycobacterial O-methyl-D-glucose polysaccharide and lipopolysaccharides. Carbohydr. Res. 1983; 120: 95.
    • (1983) Carbohydr. Res. , vol.120 , pp. 95
    • Dell, A.1    Ballou, C.E.2
  • 5
    • 0025271979 scopus 로고
    • Determination of linkage position and identification of the reducing linear oligosaccharides by negative ion fast atom bombardment mass spectrometry
    • Garozzo D, Giuffrida M, Impallomeni G, Ballistreri A, Montaudo G. Determination of linkage position and identification of the reducing linear oligosaccharides by negative ion fast atom bombardment mass spectrometry. Anal. Chem. 1990; 62: 279.
    • (1990) Anal. Chem. , vol.62 , pp. 279
    • Garozzo, D.1    Giuffrida, M.2    Impallomeni, G.3    Ballistreri, A.4    Montaudo, G.5
  • 6
    • 0027617018 scopus 로고
    • Liquid secondary ion mass spectrometry/Fourier transform mass spectrometry of oligosaccharide anions
    • Carroll JA, Ngoka L, Lambert CG, Lebrilla CB. Liquid secondary ion mass spectrometry/Fourier transform mass spectrometry of oligosaccharide anions. Anal. Chem. 1993; 65: 1582.
    • (1993) Anal. Chem. , vol.65 , pp. 1582
    • Carroll, J.A.1    Ngoka, L.2    Lambert, C.G.3    Lebrilla, C.B.4
  • 7
    • 0029079454 scopus 로고
    • Energetic of cross-ring cleavages and their relevance to the linkage determination of oligosaccharides
    • Carroll JA, Willard D, Lebrilla CB. Energetic of cross-ring cleavages and their relevance to the linkage determination of oligosaccharides. Anal. Chim. Acta 1995; 307: 431.
    • (1995) Anal. Chim. Acta , vol.307 , pp. 431
    • Carroll, J.A.1    Willard, D.2    Lebrilla, C.B.3
  • 9
    • 0029155896 scopus 로고
    • Determination of both linkage position and anomeric configuration in underivatized glucopyranosyl disaccharides by electrospray mass spectrometry
    • Mulroney B, Traeger JC, Stone BA. Determination of both linkage position and anomeric configuration in underivatized glucopyranosyl disaccharides by electrospray mass spectrometry. J. Mass Spectrom. 1995; 30: 1277.
    • (1995) J. Mass Spectrom. , vol.30 , pp. 1277
    • Mulroney, B.1    Traeger, J.C.2    Stone, B.A.3
  • 12
    • 0032949576 scopus 로고    scopus 로고
    • Relative gas phase acidities of D-glucopyranose from molecular orbital calculations
    • Mulroney B, Peel JB, Traeger JC, Stone BA. Relative gas phase acidities of D-glucopyranose from molecular orbital calculations. J. Mass Spectrom. 1999; 34: 544.
    • (1999) J. Mass Spectrom. , vol.34 , pp. 544
    • Mulroney, B.1    Peel, J.B.2    Traeger, J.C.3    Stone, B.A.4
  • 13
    • 0029079454 scopus 로고
    • Energetics of cross-ring cleavages and their relevance to the linkage determination of oligasaccharides
    • Carroll JA, Willard D, Lebrilla CB. Energetics of cross-ring cleavages and their relevance to the linkage determination of oligasaccharides. Anal. Chim. Acta 1995; 307: 431.
    • (1995) Anal. Chim. Acta , vol.307 , pp. 431
    • Carroll, J.A.1    Willard, D.2    Lebrilla, C.B.3
  • 14
    • 0013228897 scopus 로고    scopus 로고
    • Evaluation of the role of multiple hydrogen bonding in offering stability to negative ion adducts in electrospray mass spectrometry
    • Cai Y, Concha MC, Murray JS, Cole RB. Evaluation of the role of multiple hydrogen bonding in offering stability to negative ion adducts in electrospray mass spectrometry. J. Am. Soc. Mass Spectrom. 2002; 13: 1360.
    • (2002) J. Am. Soc. Mass Spectrom. , vol.13 , pp. 1360
    • Cai, Y.1    Concha, M.C.2    Murray, J.S.3    Cole, R.B.4
  • 15
    • 0141618776 scopus 로고    scopus 로고
    • Gas-phase reactivity of lead(II) ions with D-glucose. A combined electrospray ionization mass spectrometry and theoretical study
    • Salpin JY, Tortajada J. Gas-phase reactivity of lead(II) ions with D-glucose. A combined electrospray ionization mass spectrometry and theoretical study. J. Phys. Chem. A 2003; 107: 2943.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 2943
    • Salpin, J.Y.1    Tortajada, J.2
  • 17
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993; 98: 5648.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648
    • Becke, A.D.1
  • 18
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B: Condens. Matter 1988; 37: 785.
    • (1988) Phys. Rev. B: Condens. Matter , vol.37 , pp. 785
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 19
    • 0042842707 scopus 로고    scopus 로고
    • 2O complexes as prototypes of multiple hydrogen bond systems
    • 2O complexes as prototypes of multiple hydrogen bond systems. J. Comput. Chem. 1997; 18: 1124.
    • (1997) J. Comput. Chem. , vol.18 , pp. 1124
    • González, L.1    Mó, O.2    Yáñez, M.3
  • 20
    • 0031344659 scopus 로고    scopus 로고
    • High-level ab initio calculations on the intramolecular hydrogen bond in thiomalonaldehyde
    • González L, Mó O, Yáñez M. High-level ab initio calculations on the intramolecular hydrogen bond in thiomalonaldehyde. J. Phys. Chem. A 1997; 101: 9710.
    • (1997) J. Phys. Chem. A , vol.101 , pp. 9710
    • González, L.1    Mó, O.2    Yáñez, M.3
  • 22
    • 84986468715 scopus 로고
    • Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21 + G basis set for first-row elements Li-F
    • Clark T, Chandrasekhar J, Spitznagel GW, Schleyer PvR. Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21 + G basis set for first-row elements Li-F. J. Comput. Chem. 1983; 4: 294.
    • (1983) J. Comput. Chem. , vol.4 , pp. 294
    • Clark, T.1    Chandrasekhar, J.2    Spitznagel, G.W.3    Schleyer, Pv.R.4
  • 24
    • 0011083499 scopus 로고
    • Intramolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • Reed AE, Curtiss LA, Weinhold F. Intramolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988; 88: 899.
    • (1988) Chem. Rev. , vol.88 , pp. 899
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 26
    • 34547779168 scopus 로고
    • Gas-phase acidities: A comparison of density functional, MP2, MP4, F4, G2(MP2,SVP), G2(MP2), and G2 procedures
    • Smith BJ, Radom L. Gas-phase acidities: a comparison of density functional, MP2, MP4, F4, G2(MP2,SVP), G2(MP2), and G2 procedures. Chem. Phys Lett. 1993; 245: 123.
    • (1993) Chem. Phys. Lett. , vol.245 , pp. 123
    • Smith, B.J.1    Radom, L.2
  • 27
    • 22244435668 scopus 로고    scopus 로고
    • Calculated gas-phase acidities using density functional theory: Is it reliable?
    • Merrill GN, Kass Sr. Calculated gas-phase acidities using density functional theory: is it reliable ? J. Phys. Chem. 1996; 100: 17 465.
    • (1996) J. Phys. Chem. , vol.100 , pp. 17465
    • Merrill, G.N.1    Kass, Sr.2
  • 28
    • 0001759766 scopus 로고    scopus 로고
    • Gas-phase protolysis between neutral Brøonsted acid and a neutral Brøonsted base?
    • Catalán J, Palomar J. Gas-phase protolysis between neutral Brøonsted acid and a neutral Brøonsted base? Chem. Phys. Lett. 1998; 293: 511.
    • (1998) Chem. Phys. Lett. , vol.293 , pp. 511
    • Catalán, J.1    Palomar, J.2
  • 29
    • 0001520083 scopus 로고    scopus 로고
    • Critical test of performance of B3LYP functional for prediction of gas-phase acidities and basicities
    • Burk P, Koppel IA, Koppel I, Leito I, Travnikova O. Critical test of performance of B3LYP functional for prediction of gas-phase acidities and basicities. Chem. Phys. Lett. 2000; 323: 482.
    • (2000) Chem. Phys. Lett. , vol.323 , pp. 482
    • Burk, P.1    Koppel, I.A.2    Koppel, I.3    Leito, I.4    Travnikova, O.5
  • 31
    • 0141917879 scopus 로고    scopus 로고
    • NIST Standard Reference Database Number 69
    • NIST Chemistry Webbook. NIST Standard Reference Database Number 69,2000; http://webbook.nist.gov/chemistry.
    • (2000) NIST Chemistry Webbook
  • 32
    • 0037167785 scopus 로고    scopus 로고
    • Anchoring the gas-phase acidity scale
    • Ervin KJM, DeTuri VF. Anchoring the gas-phase acidity scale. J. Phys. Chem. A 2002; 106: 9947.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 9947
    • Ervin, K.J.M.1    DeTuri, V.F.2
  • 33
    • 0000557279 scopus 로고
    • Quantum chemical conformational analysis of glucose in aqueous solution
    • Cramer CJ, Truhlar DG. Quantum chemical conformational analysis of glucose in aqueous solution. J. Am. Chem. Soc. 1993; 115: 5745.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5745
    • Cramer, C.J.1    Truhlar, D.G.2
  • 34
    • 0001339474 scopus 로고
    • Solvation effects on conformational equilibria. Studies related to the conformational properties of 2-methoxytetrahydropyrans and related methyl glucopyranosides
    • Lemieux RU, Pavia AA, Martin JC, Watanabe KA. Solvation effects on conformational equilibria. Studies related to the conformational properties of 2-methoxytetrahydropyrans and related methyl glucopyranosides. Can. J. Chem. 1969; 47: 4427.
    • (1969) Can. J. Chem. , vol.47 , pp. 4427
    • Lemieux, R.U.1    Pavia, A.A.2    Martin, J.C.3    Watanabe, K.A.4
  • 35
    • 0001412364 scopus 로고
    • Ab initio examination of anomeric effects in tetrahydropyrans, 1,3-dioxanes, and glucose
    • Salzner U, Schleyer PvR. Ab initio examination of anomeric effects in tetrahydropyrans, 1,3-dioxanes, and glucose. J. Org. Chem. 1994; 59: 2138.
    • (1994) J. Org. Chem. , vol.59 , pp. 2138
    • Salzner, U.1    Schleyer, Pv.R.2
  • 36
    • 0002965416 scopus 로고
    • Stability of glycosides to acid hydrolysis
    • Edward JT. Stability of glycosides to acid hydrolysis. Chem. Ind. (London) 1955; 1102.
    • (1955) Chem. Ind. (London) , pp. 1102
    • Edward, J.T.1
  • 37
    • 0342892105 scopus 로고
    • 1H-NMR studies of (6r)- and (6s)-deuterated D-hexoses: Assignment of the preferred rotamers about C5 - C6 bond of D-glucose and D-galactose derivatives in solutions
    • 1H-NMR studies of (6r)- and (6s)-deuterated D-hexoses: assignment of the preferred rotamers about C5-C6 bond Of D-glucose and D-galactose derivatives in solutions. Tetrahedron Lett. 1984; 25: 1575.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 1575
    • Nishida, Y.1    Ohrui, H.2    Meguro, H.3
  • 38
    • 7344264202 scopus 로고
    • American Chemical Society: Washington, DC
    • Goud RF. Carbohydrates in Solution, vol. 117. American Chemical Society: Washington, DC, 1971.
    • (1971) Carbohydrates in Solution , vol.117
    • Goud, R.F.1
  • 40
    • 0029925988 scopus 로고    scopus 로고
    • Ab initio studies of the exocyclic hydroxymethyl rotational surface in α-D-glucopyranose
    • Brown JW, Wadlowski BD. Ab initio studies of the exocyclic hydroxymethyl rotational surface in α-D-glucopyranose. J. Am. Chem. Soc. 1996; 118:1190.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1190
    • Brown, J.W.1    Wadlowski, B.D.2
  • 41
    • 84962426047 scopus 로고    scopus 로고
    • Exocyclic hydroxymethyl rotational conformers of β- and α-D-glucopyranose in the gas-phase and in aqueous solution
    • Wadlowski BD,Chenoweth SA, Jones KE, Brown JW. Exocyclic hydroxymethyl rotational conformers of β- and α -D-glucopyranose in the gas-phase and in aqueous solution. J. Phys. Chem. A 1998; 102: 5086.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 5086
    • Wadlowski, B.D.1    Chenoweth, S.A.2    Jones, K.E.3    Brown, J.W.4
  • 42
    • 84962349279 scopus 로고    scopus 로고
    • The epimerisation of 2-hydropyranol catalysed by the tautomeric couples 2-pyridone/2-hydroxypridine and formamide/formamidic acid as a model for the sugar's mutarotation: A theoretical study
    • Morpurgo S, Bossa M. The epimerisation of 2-hydropyranol catalysed by the tautomeric couples 2-pyridone/2-hydroxypridine and formamide/formamidic acid as a model for the sugar's mutarotation: a theoretical study. Phys. Chem. Chem. Phys. 2003; 5: 1181.
    • (2003) Phys. Chem. Chem. Phys. , vol.5 , pp. 1181
    • Morpurgo, S.1    Bossa, M.2
  • 44
    • 0002086698 scopus 로고
    • The entropies of polyatomic gaseous ions
    • Loewenschuss A, Marcus Y. The entropies of polyatomic gaseous ions. Chem. Rev. 1984; 84: 89.
    • (1984) Chem. Rev. , vol.84 , pp. 89
    • Loewenschuss, A.1    Marcus, Y.2
  • 45
    • 0036500612 scopus 로고    scopus 로고
    • Stabilization of anionic adducts in negative ion electrospray mass spectrometry
    • Cai Y, Cole RB. Stabilization of anionic adducts in negative ion electrospray mass spectrometry. Anal. Chem. 2002; 74: 985.
    • (2002) Anal. Chem. , vol.74 , pp. 985
    • Cai, Y.1    Cole, R.B.2
  • 46
    • 0000535425 scopus 로고
    • Hemiacetal anions: A model for tetrahedral reaction intermediates
    • Baer S, Brinkman EA, Brauman JI. Hemiacetal anions: a model for tetrahedral reaction intermediates. J. Am. Chem. Soc. 1991; 113: 805.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 805
    • Baer, S.1    Brinkman, E.A.2    Brauman, J.I.3


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