메뉴 건너뛰기




Volumn 45, Issue 5, 2005, Pages 1223-1236

Information content in organic molecules: Aggregation states and solvent effects

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; FUNCTIONS; ORGANIC COMPOUNDS; SOLVENTS; VACUUM;

EID: 26944450094     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci050101m     Document Type: Article
Times cited : (26)

References (54)
  • 1
    • 84856043672 scopus 로고
    • A mathematical theory of communication
    • Shannon, C. E. A Mathematical Theory of Communication. Bell Syst. Tech. J. 1948, 27, 379.
    • (1948) Bell Syst. Tech. J. , vol.27 , pp. 379
    • Shannon, C.E.1
  • 3
    • 84980082497 scopus 로고
    • Certain factors affecting telegraph speed
    • Nyquist, H. Certain Factors Affecting Telegraph Speed. Bell Syst. Tech. J. 1924, April, 324.
    • (1924) Bell Syst. Tech. J. , vol.APRIL , pp. 324
    • Nyquist, H.1
  • 4
    • 84980082105 scopus 로고
    • Transmission of information
    • Hartley, R. V. L. Transmission of Information. Bell Syst. Tech. J. 1928, July, 535.
    • (1928) Bell Syst. Tech. J. , vol.JULY , pp. 535
    • Hartley, R.V.L.1
  • 5
    • 84939431353 scopus 로고
    • Theory of statistical estimation
    • See, for example, Fisher, R. A. Theory of Statistical Estimation. Proc. Cambridge Philos. Soc. 1925, 22, 700.
    • (1925) Proc. Cambridge Philos. Soc. , vol.22 , pp. 700
    • Fisher, R.A.1
  • 6
    • 0004280469 scopus 로고
    • Dover Publications: New York, Chapter 1
    • Ash, R. B. Information Theory; Dover Publications: New York, 1990; Chapter 1.
    • (1990) Information Theory
    • Ash, R.B.1
  • 7
    • 0002631773 scopus 로고
    • The information theoretic approach to molecular reaction dynamics
    • Exceptions involve gas-phase reactions amenable to high-resolution spectroscopy. See Levine, R. D. The Information Theoretic Approach to Molecular Reaction Dynamics. Annu. Rev. Phys. Chem. 1978, 29, 59.
    • (1978) Annu. Rev. Phys. Chem. , vol.29 , pp. 59
    • Levine, R.D.1
  • 8
    • 0343071989 scopus 로고
    • Information theory, distance matrix, and molecular branching
    • Bonchev, D.; Trinajstic, N. Information Theory, Distance Matrix, and Molecular Branching. J. Chem. Phys. 1978, 67, 4517.
    • (1978) J. Chem. Phys. , vol.67 , pp. 4517
    • Bonchev, D.1    Trinajstic, N.2
  • 9
    • 0000524226 scopus 로고
    • The first general index of molecular complexity
    • Bertz, S. H. The First General Index of Molecular Complexity. J. Am. Chem. Soc. 1981, 103, 3599.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3599
    • Bertz, S.H.1
  • 10
    • 0002220828 scopus 로고
    • Topological indices and chemical reactivity
    • Bonchev, D., Mekenyan, O., Eds; Kluwer Academic: Dordrecht, The Netherlands, Chapter VIII
    • Basak, S. C.; Mekenyan, O. Topological Indices and Chemical Reactivity. In Graph Theoretical Approaches to Chemical Reactivity; Bonchev, D., Mekenyan, O., Eds; Kluwer Academic: Dordrecht, The Netherlands, 1994; Chapter VIII, p 221.
    • (1994) Graph Theoretical Approaches to Chemical Reactivity , pp. 221
    • Basak, S.C.1    Mekenyan, O.2
  • 11
    • 0000228805 scopus 로고    scopus 로고
    • Variability of molecular descriptors in compound databases revealed by shannon entropy calculations
    • Godden, J. W.; Stahura, F. L.; Bajorath, J. Variability of Molecular Descriptors in Compound Databases Revealed by Shannon Entropy Calculations. J. Chem. Inf. Comput. Sci. 2000, 40, 796.
    • (2000) J. Chem. Inf. Comput. Sci. , vol.40 , pp. 796
    • Godden, J.W.1    Stahura, F.L.2    Bajorath, J.3
  • 12
    • 0034268411 scopus 로고    scopus 로고
    • Distinguishing between natural products and synthetic molecules by descriptor shannon entropy analysis and binary QSAR calculations
    • Stahura, F. L.; Godden, J. W.; Xue, L.; Bajorath, J. Distinguishing Between Natural Products and Synthetic Molecules by Descriptor Shannon Entropy Analysis and Binary QSAR Calculations. J. Chem. Inf. Comput. Sci. 2000, 40, 1245.
    • (2000) J. Chem. Inf. Comput. Sci. , vol.40 , pp. 1245
    • Stahura, F.L.1    Godden, J.W.2    Xue, L.3    Bajorath, J.4
  • 13
    • 0035412802 scopus 로고    scopus 로고
    • Differential shannon entropy as a sensitive measure of differences in database variability of molecular descriptors
    • Godden, J. W.; Bajorath, J. Differential Shannon Entropy as a Sensitive Measure of Differences in Database Variability of Molecular Descriptors. J. Chem. Inf. Comput. Sci. 2001, 41, 1060.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 1060
    • Godden, J.W.1    Bajorath, J.2
  • 14
    • 0036432427 scopus 로고    scopus 로고
    • Chemical descriptors of distinct levels of information content and varying sensitivity to differences between selected compound databases identified by SE-DSE analysis
    • Godden, J. W.; Bajorath, J. Chemical Descriptors of Distinct Levels of Information Content and Varying Sensitivity to Differences Between Selected Compound Databases Identified by SE-DSE Analysis. J. Chem. Inf. Comput. Sci. 2002, 42, 87.
    • (2002) J. Chem. Inf. Comput. Sci. , vol.42 , pp. 87
    • Godden, J.W.1    Bajorath, J.2
  • 15
    • 0002291769 scopus 로고    scopus 로고
    • Use of graph-theoretic and gemoetrical molecular descriptors in structure-activity relationships
    • Balaban, A. T., Ed.; Plenum Press: New York, Chapter IV
    • Basak, S. C.; Grunwald, G. D.; Niemi, G. J. Use of Graph-Theoretic and Gemoetrical Molecular Descriptors in Structure-Activity Relationships. In From Chemical Topology to Three-Dimensional Geometry; Balaban, A. T., Ed.; Plenum Press: New York, 1997; Chapter IV, p 73.
    • (1997) From Chemical Topology to Three-dimensional Geometry , pp. 73
    • Basak, S.C.1    Grunwald, G.D.2    Niemi, G.J.3
  • 16
    • 0035292795 scopus 로고    scopus 로고
    • Selected concepts and investigations in compound classification, molecular descriptor analysis, and virtual screening
    • Bajorath, J. Selected Concepts and Investigations in Compound Classification, Molecular Descriptor Analysis, and Virtual Screening. J. Chem. Inf. Comput. Sci. 2001, 41, 233.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 233
    • Bajorath, J.1
  • 18
    • 0011421663 scopus 로고    scopus 로고
    • Base information content in organic molecular formulae
    • Graham, D. J.; Schacht, D. Base Information Content in Organic Molecular Formulae. J. Chem. Inf. Comput. Sci. 2000, 40, 942.
    • (2000) J. Chem. Inf. Comput. Sci. , vol.40 , pp. 942
    • Graham, D.J.1    Schacht, D.2
  • 19
    • 0036522731 scopus 로고    scopus 로고
    • Information content in organic molecules: Structure considerations based on integer statistics
    • Graham, D. J. Information Content in Organic Molecules: Structure Considerations Based On Integer Statistics. J. Chem. Inf. Comput. Sci. 2002, 42, 215.
    • (2002) J. Chem. Inf. Comput. Sci. , vol.42 , pp. 215
    • Graham, D.J.1
  • 20
    • 5444258821 scopus 로고    scopus 로고
    • Information content in organic molecules: Quantification and statistical structure via brownian processing
    • Graham, D. J.; Malarkey, C.; Schulmerich, M. V. Information Content in Organic Molecules: Quantification and Statistical Structure Via Brownian Processing. J. Chem. Inf. Comput. Sci. 2004, 44, 1601.
    • (2004) J. Chem. Inf. Comput. Sci. , vol.44 , pp. 1601
    • Graham, D.J.1    Malarkey, C.2    Schulmerich, M.V.3
  • 21
    • 5444225985 scopus 로고    scopus 로고
    • Information content in organic molecules: Reaction pathway analysis via brownian processing
    • Graham, D. J.; Schulmerich, M. V. Information Content in Organic Molecules: Reaction Pathway Analysis Via Brownian Processing. J. Chem. Inf. Comput. Sci. 2004, 44, 1612.
    • (2004) J. Chem. Inf. Comput. Sci. , vol.44 , pp. 1612
    • Graham, D.J.1    Schulmerich, M.V.2
  • 22
    • 0010146684 scopus 로고
    • Thermodynamics of computation - A review
    • Bennett, C. H. Thermodynamics of Computation - A Review. Int. J. Theor. Phys. 1982, 21, 905.
    • (1982) Int. J. Theor. Phys. , vol.21 , pp. 905
    • Bennett, C.H.1
  • 23
    • 0004193807 scopus 로고    scopus 로고
    • Hey, A. J. G., Allen, R. W., Eds.; Addison-Wesley: Reading, Massachusetts
    • See also Feynman, R. P. Feynman Lectures on Computation; Hey, A. J. G., Allen, R. W., Eds.; Addison-Wesley: Reading, Massachusetts, 1996.
    • (1996) Feynman Lectures on Computation
    • Feynman, R.P.1
  • 24
    • 0000244133 scopus 로고
    • Energy and information
    • Tribus, M.; McIrvine, E. C. Energy and Information. Sci. Am. 1971, 225, 179.
    • (1971) Sci. Am. , vol.225 , pp. 179
    • Tribus, M.1    McIrvine, E.C.2
  • 25
    • 26944441894 scopus 로고    scopus 로고
    • note
    • 3-one-5-methyl-cyclohexene was the featured molecule for Brownian processing demonstrations in ref 16.
  • 27
    • 26944453866 scopus 로고    scopus 로고
    • note
    • For the field calculations, a molecular mechanics routine obtained from CambridgeSoft Corporation (Cambridge, MA 02139) was used in conjunction with several valence bond approximations.
  • 29
    • 36849104490 scopus 로고
    • Intensity enhancement of electronic transitions by weak intermolecular interactions
    • Robinson, G. W. Intensity Enhancement of Electronic Transitions by Weak Intermolecular Interactions. J. Chem. Phys. 1967, 46, 572.
    • (1967) J. Chem. Phys. , vol.46 , pp. 572
    • Robinson, G.W.1
  • 31
    • 26944460652 scopus 로고    scopus 로고
    • Manuscript in preparation
    • Graham, D. J. Manuscript in preparation.
    • Graham, D.J.1
  • 32
    • 0004249259 scopus 로고
    • (Revised by Pitzer, K. S.; Brewer, L.); McGraw-Hill: New York, Chapter 14
    • Lewis, G. N.; Randall, M. (Revised by Pitzer, K. S.; Brewer, L.); Thermodynamics; McGraw-Hill: New York, 1991; Chapter 14.
    • (1991) Thermodynamics
    • Lewis, G.N.1    Randall, M.2
  • 36
    • 26944503919 scopus 로고
    • Prentice Hall: Englewood Cliffs, NJ, Chapter 19
    • A values for acetic acid derivatives reported in other texts to be somewhat different. See Morrison, R. T.; Boyd, R. N. Organic Chemistry, 6th ed.; Prentice Hall: Englewood Cliffs, NJ, 1992; Chapter 19, p 735.
    • (1992) Organic Chemistry, 6th Ed. , pp. 735
    • Morrison, R.T.1    Boyd, R.N.2
  • 39
    • 0002118048 scopus 로고
    • Keto-enol equilibrium constants
    • Rappoport, Z., Ed.; Wiley: New York, Chapter 6
    • Toullec, J. Keto-Enol Equilibrium Constants. In The Chemistry of Enols; Rappoport, Z., Ed.; Wiley: New York, 1990; Chapter 6.
    • (1990) The Chemistry of Enols
    • Toullec, J.1
  • 40
    • 84981761395 scopus 로고
    • Uber die Tautomerie des Acetessigesters. (Uber Keto-Enol-Tautomerie III)
    • Meyer, K. H.; Kappelmeier, P. Uber die Tautomerie des Acetessigesters. (Uber Keto-Enol-Tautomerie III). Chem. Ber. 1911, 44, 2718.
    • (1911) Chem. Ber. , vol.44 , pp. 2718
    • Meyer, K.H.1    Kappelmeier, P.2
  • 41
    • 84932968891 scopus 로고
    • Uber den Zusammenhang zwischen Konstitution und Gleichgewicht bei keto-enol-desmotropen Verbindugen. (Uber Keto-Enol Tautomerie. VI)
    • Meyer, K. H. Uber den Zusammenhang zwischen Konstitution und Gleichgewicht bei keto-enol-desmotropen Verbindugen. (Uber Keto-Enol Tautomerie. VI). Chem. Ber. 1912, 45, 2846.
    • (1912) Chem. Ber. , vol.45 , pp. 2846
    • Meyer, K.H.1
  • 42
    • 0039702540 scopus 로고
    • The free energy of enolization in the gaseous phase of substituted acetoacetic esters
    • Conant, J. B.; Thompson, A. F., Jr. The Free Energy of Enolization in the Gaseous Phase of Substituted Acetoacetic Esters. J. Am. Chem. Soc. 1932, 54, 4039.
    • (1932) J. Am. Chem. Soc. , vol.54 , pp. 4039
    • Conant, J.B.1    Thompson Jr., A.F.2
  • 43
    • 0001395708 scopus 로고
    • Gas-phase 1H NMR studies of keto-enol tautomerism of acetylacetone, methyl acetoacetate, and ethyl acetoacetate
    • See, for example, Folkendt, M. M.; Weiss-Lopez, B. E.; Chauvel, J. P., Jr.; True, N. S. Gas-Phase 1H NMR Studies of Keto-Enol Tautomerism of Acetylacetone, Methyl Acetoacetate, and Ethyl Acetoacetate. J. Phys. Chem. 1985, 89, 3347.
    • (1985) J. Phys. Chem. , vol.89 , pp. 3347
    • Folkendt, M.M.1    Weiss-Lopez, B.E.2    Chauvel Jr., J.P.3    True, N.S.4
  • 45
    • 0037019620 scopus 로고    scopus 로고
    • Modulation of tautomeric equilibria by ionic clusters. Acetylacetone in solutions of lithium perchlorate-dethyl ether
    • Pocker, Y.; Spyridis, G. Modulation of Tautomeric Equilibria by Ionic Clusters. Acetylacetone in Solutions of Lithium Perchlorate-Dethyl Ether. J. Am. Chem. Soc. 2002, 124, 10373.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10373
    • Pocker, Y.1    Spyridis, G.2
  • 46
    • 0014934202 scopus 로고
    • Structure and activity of acetylcholine
    • Beers, W. H.; Reich, E. Structure and Activity of Acetylcholine. Nature 1970, 228, 917.
    • (1970) Nature , vol.228 , pp. 917
    • Beers, W.H.1    Reich, E.2
  • 47
    • 0023915747 scopus 로고
    • Synthesis, pharmacology, and molecular modeling studies of semirigid, nicotinic agonists
    • Waters, J. A.; Spivak, M.; Hermsmeier, M.; Yadav, J. S.; Liang, R. F.; Gund, T. M. Synthesis, Pharmacology, and Molecular Modeling Studies of Semirigid, Nicotinic agonists. J. Med. Chem. 1988, 31, 545.
    • (1988) J. Med. Chem. , vol.31 , pp. 545
    • Waters, J.A.1    Spivak, M.2    Hermsmeier, M.3    Yadav, J.S.4    Liang, R.F.5    Gund, T.M.6
  • 48
    • 0024543906 scopus 로고
    • Carbamyl analogues of potent, nicotinic agonists: Pharmacology and computer assisted molecular modeling study
    • Spivak, C. E.; Yadav, J. S.; Shang, W. C.; Hermsmeier, M.; Gund, T. M. Carbamyl Analogues of Potent, Nicotinic Agonists: Pharmacology and Computer Assisted Molecular Modeling Study. J. Med. Chem. 1989, 32, 305.
    • (1989) J. Med. Chem. , vol.32 , pp. 305
    • Spivak, C.E.1    Yadav, J.S.2    Shang, W.C.3    Hermsmeier, M.4    Gund, T.M.5
  • 49
    • 0003707473 scopus 로고    scopus 로고
    • Molecular modeling of small molecules
    • Cohen, N. C., Ed.; Academic: New York
    • Gund, T. Molecular Modeling of Small Molecules. In Guidebook on Molecular Modeling in Drug Design; Cohen, N. C., Ed.; Academic: New York, 1996.
    • (1996) Guidebook on Molecular Modeling in Drug Design
    • Gund, T.1
  • 51
    • 26944451537 scopus 로고
    • Cytochemical interpretation of the mechanism of penicillin action
    • Pratt, R.; Dufrenoy, J. Cytochemical Interpretation of the Mechanism of Penicillin Action. Bacteriol. Rev. 1948, 12, 79.
    • (1948) Bacteriol. Rev. , vol.12 , pp. 79
    • Pratt, R.1    Dufrenoy, J.2
  • 52
    • 37049112176 scopus 로고
    • Clavulanic acid, a novel β-lactam isolated from streptomyces clavuligerus; X-ray structure analysis
    • Howarth, T. T.; Brown, A. G. Clavulanic Acid, a Novel β-Lactam Isolated from Streptomyces Clavuligerus; X-ray Structure Analysis. J. Chem. Soc., Commun. 1976, 266.
    • (1976) J. Chem. Soc., Commun. , pp. 266
    • Howarth, T.T.1    Brown, A.G.2
  • 53
    • 84861265753 scopus 로고
    • Clavulanic acid and related compounds: Inhibitors of β-lactamase enzymes
    • Ganellin, C. R.; Roberts, S. M., Eds.; Academic: London
    • Brown, A. G.; Francois, I. Clavulanic Acid and Related Compounds: Inhibitors of β-Lactamase Enzymes. In Medicinal Chemistry, 2nd ed.; Ganellin, C. R.; Roberts, S. M., Eds.; Academic: London, 1993.
    • (1993) Medicinal Chemistry, 2nd Ed.
    • Brown, A.G.1    Francois, I.2
  • 54
    • 11744256643 scopus 로고
    • Molecular interactions in solution: An overview of methods based on continuous distributions of solvent
    • Tomasi, J.; Persico, M. Molecular Interactions in Solution: An overview of Methods based on Continuous Distributions of Solvent. Chem. Rev. 1994, 94, 2027.
    • (1994) Chem. Rev. , vol.94 , pp. 2027
    • Tomasi, J.1    Persico, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.