메뉴 건너뛰기




Volumn 118, Issue 21, 2014, Pages 3795-3803

Persistent intramolecular C-H···X (X = O or S) hydrogen-bonding in benzyl meldrums acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; GASES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 84901680615     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp5029245     Document Type: Article
Times cited : (15)

References (48)
  • 1
    • 0034751044 scopus 로고    scopus 로고
    • Synthetic applications of the pyrolysis of Meldrum's acid derivatives
    • Gaber, A. A. M.; McNab, H. Synthetic Applications of the Pyrolysis of Meldrums Acid Derivatives Synthesis (Stuttgart) 2001, 2059-2074 (Pubitemid 33026074)
    • (2001) Synthesis , Issue.14 , pp. 2059-2074
    • Gaber, A.E.-A.M.1    McNab, H.2
  • 2
    • 41149101973 scopus 로고    scopus 로고
    • Meldrums Acid and Related Compounds in the Synthesis of Natural Products and Analogs
    • Ivanov, A. S. Meldrums Acid and Related Compounds in the Synthesis of Natural Products and Analogs Chem. Soc. Rev. 2008, 37, 789-811
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 789-811
    • Ivanov, A.S.1
  • 3
    • 0034798239 scopus 로고    scopus 로고
    • New Insight on the Origin of the Unusual Acidity of Meldrums Acid from Ab Initio and Combined Qm/Mm Simulation Study
    • Byun, Y.; Mo, Y. R.; Gao, J. L. New Insight on the Origin of the Unusual Acidity of Meldrums Acid from Ab Initio and Combined Qm/Mm Simulation Study J. Am. Chem. Soc. 2001, 123, 3974-3979
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3974-3979
    • Byun, Y.1    Mo, Y.R.2    Gao, J.L.3
  • 4
    • 0344814478 scopus 로고
    • Meldrums Acid in Organic Synthesis
    • Chen, B. C. Meldrums Acid in Organic Synthesis Heterocycles 1991, 32, 529-597
    • (1991) Heterocycles , vol.32 , pp. 529-597
    • Chen, B.C.1
  • 6
    • 0005380512 scopus 로고
    • Meldrums Acid
    • McNab, H. Meldrums Acid Chem. Soc. Rev. 1978, 7, 345-358
    • (1978) Chem. Soc. Rev. , vol.7 , pp. 345-358
    • McNab, H.1
  • 7
    • 77949528712 scopus 로고    scopus 로고
    • Meldrums Acids and 5-Alkylidene Meldrums Acids in Catalytic Carbon-Carbon Bond-Forming Processes
    • Dumas, A. M.; Fillion, E. Meldrums Acids and 5-Alkylidene Meldrums Acids in Catalytic Carbon-Carbon Bond-Forming Processes Acc. Chem. Res. 2010, 43, 440-454
    • (2010) Acc. Chem. Res. , vol.43 , pp. 440-454
    • Dumas, A.M.1    Fillion, E.2
  • 8
    • 0000092274 scopus 로고
    • Acidity and General Base-Catalyzed Hydrolysis of Meldrums Acid and Its Methyl Derivatives
    • Pihlaja, K.; Seilo, M. Acidity and General Base-Catalyzed Hydrolysis of Meldrums Acid and Its Methyl Derivatives Acta Chem. Scand. 1969, 23, 3003-3010
    • (1969) Acta Chem. Scand. , vol.23 , pp. 3003-3010
    • Pihlaja, K.1    Seilo, M.2
  • 9
    • 0000816847 scopus 로고
    • Ion-Pairing and Reactivity of Enolate Anions 0.5. Thermodynamics of Ionization of Beta-Dicarbonyl and Tricarbonyl Compounds in Dimethylsulfoxide Solution and Ion-Pairing of Their Alkali Salts
    • Arnett, E. M.; Maroldo, S. G.; Schilling, S. L.; Harrelson, J. A. Ion-Pairing and Reactivity of Enolate Anions 0.5. Thermodynamics of Ionization of Beta-Dicarbonyl and Tricarbonyl Compounds in Dimethylsulfoxide Solution and Ion-Pairing of Their Alkali Salts J. Am. Chem. Soc. 1984, 106, 6759-6767
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 6759-6767
    • Arnett, E.M.1    Maroldo, S.G.2    Schilling, S.L.3    Harrelson, J.A.4
  • 10
    • 64549130886 scopus 로고    scopus 로고
    • Probing Persistent Intramolecular C-H···X (X = O and S, Br, Cl, and F) Bonding in Solution Using Benzyl Meldrums Acid Derivatives
    • Fillion, E.; Wilsily, A.; Fishlock, D. Probing Persistent Intramolecular C-H···X (X = O and S, Br, Cl, and F) Bonding in Solution Using Benzyl Meldrums Acid Derivatives J. Org. Chem. 2009, 74, 1259-1267
    • (2009) J. Org. Chem. , vol.74 , pp. 1259-1267
    • Fillion, E.1    Wilsily, A.2    Fishlock, D.3
  • 12
    • 64149093482 scopus 로고    scopus 로고
    • Chemical Bonding and Structure-Reactivity Correlation in Meldrums Acid: A Combined Experimental and Theoretical Electron Density Study
    • Chopra, D.; Zhurov, V. V.; Zhurova, E. A.; Pinkerton, A. A. Chemical Bonding and Structure-Reactivity Correlation in Meldrums Acid: A Combined Experimental and Theoretical Electron Density Study J. Org. Chem. 2009, 74, 2389-2395
    • (2009) J. Org. Chem. , vol.74 , pp. 2389-2395
    • Chopra, D.1    Zhurov, V.V.2    Zhurova, E.A.3    Pinkerton, A.A.4
  • 14
    • 3042533519 scopus 로고    scopus 로고
    • Progress toward understanding the nature and function of C-HO interactions
    • DOI 10.2174/1385272043370384
    • Castellano, R. K. Progress toward Understanding the Nature and Function of C-H···O Interactions Curr. Org. Chem. 2004, 8, 845-865 (Pubitemid 38811435)
    • (2004) Current Organic Chemistry , vol.8 , Issue.10 , pp. 845-865
    • Castellano, R.K.1
  • 15
    • 0037016451 scopus 로고    scopus 로고
    • The hydrogen bond in the solid state
    • DOI 10.1002 /1521-3773 (20020104) 41:1<48::AID-ANIE48>3.0.CO;2-U
    • Steiner, T. The Hydrogen Bond in the Solid State Angew. Chem., Int. Ed. 2002, 41, 48-76 (Pubitemid 34081196)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.1 , pp. 48-76
    • Steiner, T.1
  • 16
    • 0001438987 scopus 로고
    • Chelation of Gas-Phase Anions: An Ion-Cyclotron Resonance Study of Cooperative Binding to Fluoride and Chloride-Ions
    • Larson, J. W.; McMahon, T. B. Chelation of Gas-Phase Anions: An Ion-Cyclotron Resonance Study of Cooperative Binding to Fluoride and Chloride-Ions J. Phys. Chem. 1984, 88, 1083-1086
    • (1984) J. Phys. Chem. , vol.88 , pp. 1083-1086
    • Larson, J.W.1    McMahon, T.B.2
  • 17
    • 0001558837 scopus 로고
    • The Anomalous Gas-Phase Acidity of Ethyl Fluoride: An Ab Initio Investigation of the Importance of Hydrogen-Bonding between F- and Sp2 C-H Bonds
    • Roy, M.; McMahon, T. B. The Anomalous Gas-Phase Acidity of Ethyl Fluoride: An Ab Initio Investigation of the Importance of Hydrogen-Bonding between F- and Sp2 C-H Bonds Can. J. Chem. 1985, 63, 708-715
    • (1985) Can. J. Chem. , vol.63 , pp. 708-715
    • Roy, M.1    McMahon, T.B.2
  • 21
    • 84860505108 scopus 로고    scopus 로고
    • Structure, Energetics and Vibrational Spectra of Protonated Chlortetracycline in the Gas Phase: An Experimental and Computational Investigation
    • Ziegler, B. E.; Marta, R. A.; Martens, S. M.; Martens, J. K.; McMahon, T. B. Structure, Energetics and Vibrational Spectra of Protonated Chlortetracycline in the Gas Phase: An Experimental and Computational Investigation Int. J. Mass Spectrom. 2012, 316, 117-125
    • (2012) Int. J. Mass Spectrom. , vol.316 , pp. 117-125
    • Ziegler, B.E.1    Marta, R.A.2    Martens, S.M.3    Martens, J.K.4    McMahon, T.B.5
  • 22
    • 0000560869 scopus 로고    scopus 로고
    • Global optimization by basin-hopping and the lowest energy structures of Lennard-Jones clusters containing up to 110 atoms
    • Wales, D. J.; Doye, J. P. K. Global Optimization by Basin-Hopping and the Lowest Energy Structures of Lennard-Jones Clusters Containing up to 110 Atoms J. Phys. Chem. A 1997, 101, 5111-5116 (Pubitemid 127578169)
    • (1997) Journal of Physical Chemistry A , vol.101 , Issue.28 , pp. 5111-5116
    • Wales, D.J.1    Doye, J.P.K.2
  • 23
    • 84886891017 scopus 로고    scopus 로고
    • Proton-Bound 3-Cyanophenylalanine Trimethylamine Clusters: Isomer-Specific Fragmentation Pathways and Evidence of Gas-Phase Zwitterions
    • Hopkins, W. S.; Marta, R. A.; McMahon, T. B. Proton-Bound 3-Cyanophenylalanine Trimethylamine Clusters: Isomer-Specific Fragmentation Pathways and Evidence of Gas-Phase Zwitterions J. Phys. Chem. A 2013, 117, 10714-10718
    • (2013) J. Phys. Chem. A , vol.117 , pp. 10714-10718
    • Hopkins, W.S.1    Marta, R.A.2    McMahon, T.B.3
  • 25
    • 84961980477 scopus 로고    scopus 로고
    • Quantum mechanical continuum solvation models
    • DOI 10.1021/cr9904009
    • Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models Chem. Rev. 2005, 105, 2999-3093 (Pubitemid 41222791)
    • (2005) Chemical Reviews , vol.105 , Issue.8 , pp. 2999-3093
    • Tomasi, J.1    Mennucci, B.2    Cammi, R.3
  • 26
    • 0029633186 scopus 로고
    • Amber, a Package of Computer-Programs for Applying Molecular Mechanics, Normal-Mode Analysis, Molecular Dynamics and Free-Energy Calculations to Simulate the Structural and Energetic Properties of Molecules
    • Pearlman, D. A.; Case, D. A.; Caldwell, J. W.; Ross, W. S.; Cheatham, T. E.; Debolt, S.; Ferguson, D.; Seibel, G.; Kollman, P. Amber, a Package of Computer-Programs for Applying Molecular Mechanics, Normal-Mode Analysis, Molecular Dynamics and Free-Energy Calculations to Simulate the Structural and Energetic Properties of Molecules Comput. Phys. Commun. 1995, 91, 1-41
    • (1995) Comput. Phys. Commun. , vol.91 , pp. 1-41
    • Pearlman, D.A.1    Case, D.A.2    Caldwell, J.W.3    Ross, W.S.4    Cheatham, T.E.5    Debolt, S.6    Ferguson, D.7    Seibel, G.8    Kollman, P.9
  • 28
    • 34250727254 scopus 로고
    • Comparison of Atomic Charges Derived Via Different Procedures
    • Wiberg, K. B.; Rablen, P. R. Comparison of Atomic Charges Derived Via Different Procedures J. Comput. Chem. 1993, 14, 1504-1518
    • (1993) J. Comput. Chem. , vol.14 , pp. 1504-1518
    • Wiberg, K.B.1    Rablen, P.R.2
  • 29
    • 17144408314 scopus 로고    scopus 로고
    • Carborane acids. New "strong yet gentle" acids for organic and inorganic chemistry
    • DOI 10.1039/b415425h
    • Reed, C. A. Carborane Acids. New "Strong yet Gentle" Acids for Organic and Inorganic Chemistry Chem. Commun. 2005, 1669-1677 (Pubitemid 40524119)
    • (2005) Chemical Communications , Issue.13 , pp. 1669-1677
    • Reed, C.A.1
  • 31
    • 11744305193 scopus 로고
    • Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations
    • Wolinski, K.; Hinton, J. F.; Pulay, P. Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations J. Am. Chem. Soc. 1990, 112, 8251-8260
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8251-8260
    • Wolinski, K.1    Hinton, J.F.2    Pulay, P.3
  • 32
    • 36048996913 scopus 로고    scopus 로고
    • Basis set limit coupled cluster study of H-bonded systems and assessment of more approximate methods
    • DOI 10.1021/jp072431a
    • Boese, A. D.; Martin, J. M. L.; Klopper, W. Basis Set Limit Coupled Cluster Study of H-Bonded Systems and Assessment of More Approximate Methods J. Phys. Chem. A 2007, 111, 11122-11133 (Pubitemid 350097571)
    • (2007) Journal of Physical Chemistry A , vol.111 , Issue.43 , pp. 11122-11133
    • Boese, A.D.1    Martin, J.M.L.2    Klopper, W.3
  • 33
  • 34
    • 77951680464 scopus 로고    scopus 로고
    • A Consistent and Accurate Ab Initio Parametrization of Density Functional Dispersion Correction (Dft-D) for the 94 Elements H-Pu
    • Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A Consistent and Accurate Ab Initio Parametrization of Density Functional Dispersion Correction (Dft-D) for the 94 Elements H-Pu J. Chem. Phys. 2010, 132.
    • (2010) J. Chem. Phys. , vol.132
    • Grimme, S.1    Antony, J.2    Ehrlich, S.3    Krieg, H.4
  • 35
    • 0030051260 scopus 로고    scopus 로고
    • Synthesis of 2-substituted 1,3-oxazin-6-ones by gas-phase pyrolysis
    • DOI 10.1016/0040-4020(95)01102-1
    • McNab, H.; Withell, K. Synthesis of 2-Substituted 1,3-Oxazin-6-Ones by Gas-Phase Pyrolysis Tetrahedron 1996, 52, 3163-3170 (Pubitemid 26064977)
    • (1996) Tetrahedron , vol.52 , Issue.9 , pp. 3163-3170
    • McNab, H.1    Withell, K.2
  • 36
    • 67650217931 scopus 로고    scopus 로고
    • Scandium Triflate-Catalyzed Intramolecular Friedel-Crafts Acylation with Meldrums Acids: Insight into the Mechanism
    • Fillion, E.; Fishlock, D. Scandium Triflate-Catalyzed Intramolecular Friedel-Crafts Acylation with Meldrums Acids: Insight into the Mechanism Tetrahedron 2009, 65, 6682-6695
    • (2009) Tetrahedron , vol.65 , pp. 6682-6695
    • Fillion, E.1    Fishlock, D.2
  • 37
    • 17244367197 scopus 로고    scopus 로고
    • New scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-ζ basis Set 6-311+G(d,p)
    • DOI 10.1021/jp045733a
    • Andersson, M. P.; Uvdal, P. New Scale Factors for Harmonic Vibrational Frequencies Using the B3lyp Density Functional Method with the Triple-Xi Basis Set 6-311+G(D,P) J. Phys. Chem. A 2005, 109, 2937-2941 (Pubitemid 40527290)
    • (2005) Journal of Physical Chemistry A , vol.109 , Issue.12 , pp. 2937-2941
    • Andersson, M.P.1    Uvdal, P.2
  • 38
    • 84865706798 scopus 로고    scopus 로고
    • Protonation Preferentially Stabilizes Minor Tautomers of the Halouracils: IRMPD Action Spectroscopy and Theoretical Studies
    • Crampton, K. T.; Rathur, A. I.; Nei, Y. W.; Berden, G.; Oomens, J.; Rodgers, M. T. Protonation Preferentially Stabilizes Minor Tautomers of the Halouracils: IRMPD Action Spectroscopy and Theoretical Studies J. Am. Soc. Mass Spectrom. 2012, 23, 1469-1478
    • (2012) J. Am. Soc. Mass Spectrom. , vol.23 , pp. 1469-1478
    • Crampton, K.T.1    Rathur, A.I.2    Nei, Y.W.3    Berden, G.4    Oomens, J.5    Rodgers, M.T.6
  • 39
    • 79551697610 scopus 로고    scopus 로고
    • Chirality-Induced Conformational Preferences in Peptide-Metal Ion Binding Revealed by IR Spectroscopy
    • Dunbar, R. C.; Steill, J. D.; Oomens, J. Chirality-Induced Conformational Preferences in Peptide-Metal Ion Binding Revealed by IR Spectroscopy J. Am. Chem. Soc. 2011, 133, 1212-1215
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 1212-1215
    • Dunbar, R.C.1    Steill, J.D.2    Oomens, J.3
  • 40
    • 80052321505 scopus 로고    scopus 로고
    • Tridentate Ionic Hydrogen-Bonding Interactions of the 5-Fluorocytosine Cationic Dimer and Other 5-Fluorocytosine Analogues Characterized by Irmpd Spectroscopy and Electronic Structure Calculations
    • Martens, S. M.; Marta, R. A.; Martens, J. K.; McMahon, T. B. Tridentate Ionic Hydrogen-Bonding Interactions of the 5-Fluorocytosine Cationic Dimer and Other 5-Fluorocytosine Analogues Characterized by Irmpd Spectroscopy and Electronic Structure Calculations J. Phys. Chem. A 2011, 115, 9837-9844
    • (2011) J. Phys. Chem. A , vol.115 , pp. 9837-9844
    • Martens, S.M.1    Marta, R.A.2    Martens, J.K.3    McMahon, T.B.4
  • 41
    • 84868218130 scopus 로고    scopus 로고
    • Consecutive Fragmentation Mechanisms of Protonated Ferulic Acid Probed by Infrared Multiple Photon Dissociation Spectroscopy and Electronic Structure Calculations
    • Martens, S. M.; Marta, R. A.; Martens, J. K.; McMahon, T. B. Consecutive Fragmentation Mechanisms of Protonated Ferulic Acid Probed by Infrared Multiple Photon Dissociation Spectroscopy and Electronic Structure Calculations J. Am. Soc. Mass Spectrom. 2012, 23, 1697-1706
    • (2012) J. Am. Soc. Mass Spectrom. , vol.23 , pp. 1697-1706
    • Martens, S.M.1    Marta, R.A.2    Martens, J.K.3    McMahon, T.B.4
  • 43
    • 77749252283 scopus 로고    scopus 로고
    • Finite-Temperature IR Spectroscopy of Polyatomic Molecules: A Theoretical Assessment of Scaling Factors
    • Basire, M.; Parneix, P.; Calvo, F. Finite-Temperature IR Spectroscopy of Polyatomic Molecules: A Theoretical Assessment of Scaling Factors J. Phys. Chem. A 2010, 114, 3139-3146
    • (2010) J. Phys. Chem. A , vol.114 , pp. 3139-3146
    • Basire, M.1    Parneix, P.2    Calvo, F.3
  • 44
    • 84878098282 scopus 로고    scopus 로고
    • Accurate Modeling of Infrared Multiple Photon Dissociation Spectra: The Dynamical Role of Anharmonicities
    • Parneix, P.; Basire, M.; Calvo, F. Accurate Modeling of Infrared Multiple Photon Dissociation Spectra: The Dynamical Role of Anharmonicities J. Phys. Chem. A 2013, 117, 3954-3959
    • (2013) J. Phys. Chem. A , vol.117 , pp. 3954-3959
    • Parneix, P.1    Basire, M.2    Calvo, F.3
  • 45
    • 84891177666 scopus 로고    scopus 로고
    • H2 Ejection from Polycyclic Aromatic Hydrocarbonsl Infrared Multiphoton Dissociation of Protonated Acenaphthene and 9,10-Dihydrophenanthrene
    • Szczepanski, J.; Oomens, J.; Steill, J.; Martin, T. V. H2 Ejection from Polycyclic Aromatic Hydrocarbonsl Infrared Multiphoton Dissociation of Protonated Acenaphthene and 9,10-Dihydrophenanthrene The Astrophysical Journal 2011, 727, 1-13
    • (2011) The Astrophysical Journal , vol.727 , pp. 1-13
    • Szczepanski, J.1    Oomens, J.2    Steill, J.3    Martin, T.V.4
  • 46
    • 33745640979 scopus 로고    scopus 로고
    • Gas Phase Infrared Multiple Photon Dissociation Spectroscopy of Mass-Selected Molecular Ions
    • Oomens, J.; Sartakov, B. G.; Meijer, G.; von Helden, G. Gas Phase Infrared Multiple Photon Dissociation Spectroscopy of Mass-Selected Molecular Ions Int. J. Mass Spectrom. 2006, 254, 1-19
    • (2006) Int. J. Mass Spectrom. , vol.254 , pp. 1-19
    • Oomens, J.1    Sartakov, B.G.2    Meijer, G.3    Von Helden, G.4
  • 47
    • 0000499544 scopus 로고
    • Methyleneketenes and Methylenecarbenes 0.1. Formation of Arylmethyleneketenes and Alkylideneketenes by Pyrolysis of Substituted 2,2-Dimethyl-1,3-Dioxan-4,6-Diones
    • Brown, R. F. C.; Eastwood, F. W.; Harringt, Kj Methyleneketenes and Methylenecarbenes 0.1. Formation of Arylmethyleneketenes and Alkylideneketenes by Pyrolysis of Substituted 2,2-Dimethyl-1,3-Dioxan-4,6-Diones Aust. J. Chem. 1974, 27, 2373-2384
    • (1974) Aust. J. Chem. , vol.27 , pp. 2373-2384
    • Brown, R.F.C.1    Eastwood, F.W.2    Harringt, K.3
  • 48
    • 3042575839 scopus 로고    scopus 로고
    • Chemistry without Reagents: Synthetic Applications of Flash Vacuum Pyrolysis
    • McNab, H. Chemistry without Reagents: Synthetic Applications of Flash Vacuum Pyrolysis Aldrichimica Acta 2004, 37, 19-26
    • (2004) Aldrichimica Acta , vol.37 , pp. 19-26
    • McNab, H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.