메뉴 건너뛰기




Volumn 5, Issue 18, 2014, Pages 3211-3215

Experimental determination of the electrostatic nature of carbonyl hydrogen-bonding interactions using IR-NMR Correlations

Author keywords

Excited states; Photochemistry; Spectroscopy

Indexed keywords

ELECTROSTATICS; EXCITED STATES; PHOTOCHEMICAL REACTIONS; SPECTROSCOPY;

EID: 84990175580     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz501613p     Document Type: Article
Times cited : (34)

References (46)
  • 1
    • 0032576118 scopus 로고    scopus 로고
    • Acidity basicity, and the stability of hydrogen bonds: Complexes of RO-+ HCF3
    • Chabinyc, M. L.; Brauman, J. I. Acidity Basicity, and the Stability of Hydrogen Bonds: Complexes of RO-+ HCF3. J. Am. Chem. Soc. 1998, 120, 10863-10870.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 10863-10870
    • Chabinyc, M.L.1    Brauman, J.I.2
  • 2
    • 57349139504 scopus 로고    scopus 로고
    • Hydrogen bonding lowers intrinsic nucleophilicity of solvated nucleophiles
    • Chen, X.; Brauman, J. I. Hydrogen Bonding Lowers Intrinsic Nucleophilicity of Solvated Nucleophiles. J. Am. Chem. Soc. 2008, 130, 15038-15046.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 15038-15046
    • Chen, X.1    Brauman, J.I.2
  • 7
    • 0001482146 scopus 로고
    • Polarity and ionization from the standpoint of the lewis theory of valence
    • Latimer, W. M.; Rodebush, W. H. Polarity and Ionization from the Standpoint of the Lewis Theory of Valence. J. Am. Chem. Soc. 1920, 42, 1419-1433.
    • (1920) J. Am. Chem. Soc. , vol.42 , pp. 1419-1433
    • Latimer, W.M.1    Rodebush, W.H.2
  • 9
    • 27844483380 scopus 로고    scopus 로고
    • Energy decomposition analyses for many-body interaction and applications to water complexes
    • Chen, W.; Gordon, M. S. Energy Decomposition Analyses for Many-Body Interaction and Applications to Water Complexes. J. Phys. Chem. 1996, 100, 14316-14328.
    • (1996) J. Phys. Chem. , vol.100 , pp. 14316-14328
    • Chen, W.1    Gordon, M.S.2
  • 10
    • 33847089778 scopus 로고
    • Why do molecules interact? The origin of electron donor-acceptor complexes, hydrogen bonding and proton affinity
    • Morokuma, K. Why Do Molecules Interact? The Origin of Electron Donor-Acceptor Complexes, Hydrogen Bonding and Proton Affinity. Acc. Chem. Res. 1977, 10, 294-300.
    • (1977) Acc. Chem. Res. , vol.10 , pp. 294-300
    • Morokuma, K.1
  • 11
    • 0001108871 scopus 로고    scopus 로고
    • Ab initio study of hydrogen-bonded complexes of small organic molecules with water
    • Rablen, P.R.; Lockman, J. W.; Jorgensen, W. L. Ab Initio Study of Hydrogen-Bonded Complexes of Small Organic Molecules with Water. J. Phys. Chem. A 1998, 102, 3782-3797.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 3782-3797
    • Rablen, P.R.1    Lockman, J.W.2    Jorgensen, W.L.3
  • 12
    • 0001659759 scopus 로고
    • The validity of electrostatic predictions of the shapes of van der waals dimers
    • Rendell, A. P.; Bacskay, G B.; Hush, N. S. The Validity of Electrostatic Predictions of the Shapes of van der Waals Dimers. Chem. Phys. Lett. 1985, 117, 400-408.
    • (1985) Chem. Phys. Lett. , vol.117 , pp. 400-408
    • Rendell, A.P.1    Bacskay, G.B.2    Hush, N.S.3
  • 13
    • 43949164521 scopus 로고
    • Computation of charge-transfer energies by perturbation theory
    • Stone, A. J. Computation of Charge-Transfer Energies by Perturbation Theory. Chem. Phys. Lett. 1993, 211, 101-109.
    • (1993) Chem. Phys. Lett. , vol.211 , pp. 101-109
    • Stone, A.J.1
  • 14
    • 0003955397 scopus 로고
    • Clarendon Press: Oxford, U.K
    • Coulson, C. A Valence; Clarendon Press: Oxford, U.K., 1952.
    • (1952) Valence
    • Coulson, C.A.1
  • 15
    • 79954529867 scopus 로고    scopus 로고
    • What is the covalency of hydrogen bonding?
    • Grabowski, S.J. What Is the Covalency of Hydrogen Bonding? Chem. Rev. 2011, 111, 2597-2625.
    • (2011) Chem. Rev. , vol.111 , pp. 2597-2625
    • Grabowski, S.J.1
  • 17
    • 0001477338 scopus 로고    scopus 로고
    • Are hydrogen bonds covalent or electrostatic? A molecular orbital comparison of molecules in electric fields and H-bonding environments
    • Dannenberg, J. J.; Haskamp, L.; Masunov, A. Are Hydrogen Bonds Covalent or Electrostatic? A Molecular Orbital Comparison of Molecules in Electric Fields and H-Bonding Environments. J. Phys. Chem. A 1999, 103, 7083-7086.
    • (1999) J. Phys. Chem. A , vol.103 , pp. 7083-7086
    • Dannenberg, J.J.1    Haskamp, L.2    Masunov, A.3
  • 18
    • 84893842672 scopus 로고    scopus 로고
    • Is electrostatics sufficient to describe hydrogen-bonding interactions?
    • Hoja, J.; Sax, A. F.; Szalewicz, K. Is Electrostatics Sufficient to Describe Hydrogen-Bonding Interactions? Chem. - Eur. J. 2014, 20, 2292-2300.
    • (2014) Chem. - Eur. J , vol.20 , pp. 2292-2300
    • Hoja, J.1    Sax, A.F.2    Szalewicz, K.3
  • 19
    • 84881071656 scopus 로고    scopus 로고
    • Measuring electrostatic fields in both hydrogen-bonding and non-hydrogen-bonding environments using carbonyl vibrational probes
    • Fried, S. D.; Bagchi, S.; Boxer, S.G Measuring Electrostatic Fields in Both Hydrogen-Bonding and Non-Hydrogen-Bonding Environments Using Carbonyl Vibrational Probes. J. Am. Chem. Soc. 2013, 135, 11181-11192.
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 11181-11192
    • Fried, S.D.1    Bagchi, S.2    Boxer, S.G.3
  • 20
  • 21
    • 79955398126 scopus 로고    scopus 로고
    • Vibrational solvatochromism and electrochromism of infrared probe molecules containing C=O, C=N, C=O, or C-F vibrational chromophore
    • Choi, J.-H; Cho, M. Vibrational Solvatochromism and Electrochromism of Infrared Probe Molecules Containing C=O, C=N, C=O, or C-F Vibrational Chromophore. J. Chem. Phys. 2011, 134, 154513.
    • (2011) J. Chem. Phys. , vol.134
    • Choi, J.-H.1    Cho, M.2
  • 22
    • 84883752235 scopus 로고    scopus 로고
    • Exploring the potential of diarylacetylenediols as hydrogen bonding catalysts
    • Turkmen, Y. E.; Rawal, V. H. Exploring the Potential of Diarylacetylenediols as Hydrogen Bonding Catalysts. J. Org. Chem. 2013, 78, 8340-8353.
    • (2013) J. Org. Chem. , vol.78 , pp. 8340-8353
    • Turkmen, Y.E.1    Rawal, V.H.2
  • 23
    • 33748497291 scopus 로고    scopus 로고
    • IR spectroscopic study of hydrogen bonding using a metal carbonyl probe
    • Peris, E.; Mata, J. A.; Moliner, V. IR Spectroscopic Study of Hydrogen Bonding Using a Metal Carbonyl Probe. J. Chem. Soc., Dalton Trans. 1999, 3893-3898.
    • (1999) J. Chem. Soc., Dalton Trans. , pp. 3893-3898
    • Peris, E.1    Mata, J.A.2    Moliner, V.3
  • 24
    • 0033569391 scopus 로고    scopus 로고
    • Solvent-induced frequency shifts in the infrared spectrum of acetone in organic solvents
    • Cha, D. K.; Kloss, A. A.; Tikanen, A. C.; Fawcett, W. R. Solvent-Induced Frequency Shifts in the Infrared Spectrum of Acetone in Organic Solvents. Phys. Chem. Chem. Phys. 1999, 1, 4785-4790.
    • (1999) Phys. Chem. Chem. Phys. , vol.1 , pp. 4785-4790
    • Cha, D.K.1    Kloss, A.A.2    Tikanen, A.C.3    Fawcett, W.R.4
  • 25
    • 36849120543 scopus 로고
    • Carbon-13 chemical shifts of the carbonyl group III. Solvent effects
    • Maciel, G. E.; Natterstad, J. J. Carbon-13 Chemical Shifts of the Carbonyl Group III. Solvent Effects. J. Chem. Phys. 1965, 42, 2752-2759.
    • (1965) J. Chem. Phys. , vol.42 , pp. 2752-2759
    • Maciel, G.E.1    Natterstad, J.J.2
  • 26
    • 33947484811 scopus 로고
    • 13 chemical shift of the carbonyl group of acetone
    • 13 Chemical Shift of the Carbonyl Group of Acetone. J. Am. Chem. Soc. 1963, 85, 3903-3904.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 3903-3904
    • Maciel, G.E.1    Ruben, G.C.2
  • 27
    • 0025404291 scopus 로고
    • Infrared studies of ketones: Parameters affecting the induced carbonyl stretching vibration by solute/Solvent interaction
    • Nyquist, R. A. Infrared Studies of Ketones: Parameters Affecting the Induced Carbonyl Stretching Vibration by Solute/Solvent Interaction. Appl. Spectrosc. 1990, 44, 433-438.
    • (1990) Appl. Spectrosc. , vol.44 , pp. 433-438
    • Nyquist, R.A.1
  • 28
    • 0000435803 scopus 로고
    • Correlation of carbon-13 and oxygen-17 chemical shifts and the vibrational frequency of electrically perturbed carbon monoxide: A possible model for distal ligand effects in carbonmonoxyheme proteins
    • Augspurger, J. D.; Dykstra, C. E.; Oldfield, E. Correlation of Carbon-13 and Oxygen-17 Chemical Shifts and the Vibrational Frequency of Electrically Perturbed Carbon Monoxide: A Possible Model for Distal Ligand Effects in Carbonmonoxyheme Proteins. J. Am. Chem. Soc. 1991, 113, 2447-2451.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2447-2451
    • Augspurger, J.D.1    Dykstra, C.E.2    Oldfield, E.3
  • 30
    • 84863492163 scopus 로고    scopus 로고
    • A solvatochromic model calibrates nitriles' vibrational frequencies to electrostatic fields
    • Bagchi, S.; Fried, S. D.; Boxer, S. G. A Solvatochromic Model Calibrates Nitriles' Vibrational Frequencies to Electrostatic Fields. J. Am. Chem. Soc. 2012, 134, 10373-10376.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 10373-10376
    • Bagchi, S.1    Fried, S.D.2    Boxer, S.G.3
  • 31
    • 84869388609 scopus 로고    scopus 로고
    • Experimental quantification of electrostatics in X-H···π hydrogen bonds
    • Saggu, M.; Levinson, N. M.; Boxer, S. G. Experimental Quantification of Electrostatics in X-H···π Hydrogen bonds. J. Am. Chem. Soc. 2012, 134, 18986-18997.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 18986-18997
    • Saggu, M.1    Levinson, N.M.2    Boxer, S.G.3
  • 32
    • 80053392716 scopus 로고    scopus 로고
    • Electrostatic fields near the active site of human aldose reductase: 2. New inhibitors and complications caused by hydrogen bonds
    • Xu, L.; Cohen, A. E.; Boxer, S. G. Electrostatic Fields near the Active Site of Human Aldose Reductase: 2. New Inhibitors and Complications Caused by Hydrogen Bonds. Biochemistry 2011, 50, 8311-8322.
    • (2011) Biochemistry , vol.50 , pp. 8311-8322
    • Xu, L.1    Cohen, A.E.2    Boxer, S.G.3
  • 33
    • 0343791148 scopus 로고
    • Electric moments of molecules in liquids
    • Onsager, L. Electric Moments of Molecules in Liquids. J. Am. Chem. Soc. 1936, 58, 1486-1493.
    • (1936) J. Am. Chem. Soc. , vol.58 , pp. 1486-1493
    • Onsager, L.1
  • 34
    • 77956634583 scopus 로고    scopus 로고
    • Decomposition of vibrational shifts of nitriles into electrostatic and hydrogen-bonding effects
    • Fafarman, A. T.; Sigala, P. A.; Herschlag, D.; Boxer, S. G. Decomposition of Vibrational Shifts of Nitriles into Electrostatic and Hydrogen-Bonding Effects. J. Am. Chem. Soc. 2010, 132, 12811-12813.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 12811-12813
    • Fafarman, A.T.1    Sigala, P.A.2    Herschlag, D.3    Boxer, S.G.4
  • 35
    • 84902106697 scopus 로고    scopus 로고
    • Ester carbonyl vibration as a sensitive probe of protein local electric field
    • Pazos, I. M.; Ghosh, A.; Tucker, M. J.; Gai, F. Ester Carbonyl Vibration as a Sensitive Probe of Protein Local Electric Field. Angew. Chem., Int. Ed. 2014, 53, 6080-6084.
    • (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 6080-6084
    • Pazos, I.M.1    Ghosh, A.2    Tucker, M.J.3    Gai, F.4
  • 36
    • 0002397553 scopus 로고
    • FTIR study of the solvent influence on the carbonyl absorption peak of ethyl acetate
    • Kolling, O. W. FTIR Study of the Solvent Influence on the Carbonyl Absorption Peak of Ethyl Acetate. J. Phys. Chem. 1992, 96, 6217-6220.
    • (1992) J. Phys. Chem. , vol.96 , pp. 6217-6220
    • Kolling, O.W.1
  • 37
    • 23844509509 scopus 로고    scopus 로고
    • Chemical exchange 2D IR of hydrogen-bond making and breaking
    • Kim, Y. S.; Hochstrasser, R. M. Chemical Exchange 2D IR of Hydrogen-Bond Making and Breaking. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11185-11190.
    • (2005) Proc. Natl. Acad. Sci. U.S.A. , vol.102 , pp. 11185-11190
    • Kim, Y.S.1    Hochstrasser, R.M.2
  • 38
    • 58849154044 scopus 로고    scopus 로고
    • Ion-water hydrogen-bond switching observed with 2D IR vibrational echo chemical exchange spectroscopy
    • Moilanen, D. E.; Wong, D.; Rosenfeld, D. E.; Fenn, E. E.; Fayer, M. D. Ion-water Hydrogen-Bond Switching Observed with 2D IR Vibrational Echo Chemical Exchange Spectroscopy. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 375-380.
    • (2009) Proc. Natl. Acad. Sci. U. S. A. , vol.106 , pp. 375-380
    • Moilanen, D.E.1    Wong, D.2    Rosenfeld, D.E.3    Fenn, E.E.4    Fayer, M.D.5
  • 39
    • 66549126326 scopus 로고    scopus 로고
    • Ultrafast dynamics of hydrogen bond exchange in aqueous ionic solutions
    • Park, S.; Odelius, M.; Gaffney, K. J. Ultrafast Dynamics of Hydrogen Bond Exchange in Aqueous Ionic Solutions. J. Phys. Chem. B 2009, 113, 7825-7835.
    • (2009) J. Phys. Chem. B , vol.113 , pp. 7825-7835
    • Park, S.1    Odelius, M.2    Gaffney, K.J.3
  • 40
    • 77249131993 scopus 로고    scopus 로고
    • Hydrogen bond migration between molecular sites observed with ultrafast 2D IR chemical exchange spectroscopy
    • Rosenfeld, D. E.; Kwak, K.; Gengeliczki, Z.; Fayer, M. D. Hydrogen Bond Migration between Molecular Sites Observed with Ultrafast 2D IR Chemical Exchange Spectroscopy. J. Phys. Chem. B 2010, 114, 2383-2389.
    • (2010) J. Phys. Chem. B , vol.114 , pp. 2383-2389
    • Rosenfeld, D.E.1    Kwak, K.2    Gengeliczki, Z.3    Fayer, M.D.4
  • 41
    • 33644960056 scopus 로고    scopus 로고
    • Formation and dissociation of intra-intermolecular hydrogen-bonded solute-solvent complexes: Chemical exchange two-dimensional infrared vibrational echo spectroscopy
    • Zheng, J.; Kwak, K.; Chen, X.; Asbury, J. B.; Fayer, M. D. Formation and Dissociation of Intra-Intermolecular Hydrogen-Bonded Solute-Solvent Complexes: Chemical Exchange Two-Dimensional Infrared Vibrational Echo Spectroscopy. J. Am. Chem. Soc. 2006, 128, 2977-2987.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 2977-2987
    • Zheng, J.1    Kwak, K.2    Chen, X.3    Asbury, J.B.4    Fayer, M.D.5
  • 43
    • 67149138048 scopus 로고    scopus 로고
    • Applications of 2D IR spectroscopy to peptides, proteins, and hydrogen-bond dynamics
    • Kim, Y. S.; Hochstrasser, R. M. Applications of 2D IR Spectroscopy to Peptides, Proteins, and Hydrogen-Bond Dynamics. J. Phys. Chem. B 2009, 113, 8231-8251.
    • (2009) J. Phys. Chem. B , vol.113 , pp. 8231-8251
    • Kim, Y.S.1    Hochstrasser, R.M.2
  • 44
    • 79958232737 scopus 로고    scopus 로고
    • Collective hydrogen bond reorganization in water studied with temperature-dependent ultrafast infrared spectroscopy
    • Nicodemus, R. A.; Corcelli, S. A.; Skinner, J. L.; Tokmakoff, A. Collective Hydrogen Bond Reorganization in Water Studied with Temperature-Dependent Ultrafast Infrared Spectroscopy. J. Phys. Chem. B 2011, 115, 5604-5616.
    • (2011) J. Phys. Chem. B , vol.115 , pp. 5604-5616
    • Nicodemus, R.A.1    Corcelli, S.A.2    Skinner, J.L.3    Tokmakoff, A.4
  • 45
    • 84876770895 scopus 로고    scopus 로고
    • Chemical unfolding of chicken villin headpiece in aqueous dimethyl sulfoxide solution: Cosolvent concentration dependence, pathway, and microscopic mechanism
    • Roy, S.; Bagchi, B. Chemical Unfolding of Chicken Villin Headpiece in Aqueous Dimethyl Sulfoxide Solution: Cosolvent Concentration Dependence, Pathway, and Microscopic Mechanism. J. Phys. Chem. B 2013, 117, 4488-4502.
    • (2013) J. Phys. Chem. B , vol.117 , pp. 4488-4502
    • Roy, S.1    Bagchi, B.2
  • 46
    • 77951669558 scopus 로고    scopus 로고
    • The design of chiral double hydrogen bonding networks and their applications to catalytic asymmetric carbon-carbon and carbon-oxygen bond-forming reactions
    • Sohtome, Y.; Nagasawa, K. The Design of Chiral Double Hydrogen Bonding Networks and Their Applications to Catalytic Asymmetric Carbon-Carbon and Carbon-Oxygen Bond-Forming Reactions. Synlett 2010, 1-22.
    • (2010) Synlett , pp. 1-22
    • Sohtome, Y.1    Nagasawa, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.