메뉴 건너뛰기




Volumn 64, Issue , 2012, Pages 83-104

Quantum Chemical-QSPR Estimation of the Acidities and Basicities of Organic Compounds

Author keywords

Acidity; Basicity; PKa; QSPR; Quantum chemistry

Indexed keywords


EID: 84864336880     PISSN: 00653276     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-396498-4.00015-6     Document Type: Chapter
Times cited : (22)

References (126)
  • 2
    • 0003033213 scopus 로고
    • The determination of acidity constants
    • Cookson R.F. The determination of acidity constants. Chem. Rev. 1974, 74:5-28.
    • (1974) Chem. Rev. , vol.74 , pp. 5-28
    • Cookson, R.F.1
  • 6
    • 84864359469 scopus 로고    scopus 로고
    • CRC Press, Boca Raton, FL, 8-51, D.R. Lide, W.M. Haynes (Eds.)
    • CRC Handbook of Chemistry hand Physics 2009-2010, 8-42. CRC Press, Boca Raton, FL, 8-51. 90th ed. D.R. Lide, W.M. Haynes (Eds.).
    • (2009) CRC Handbook of Chemistry hand Physics , pp. 8-42
  • 9
    • 0023199137 scopus 로고
    • Temperature dependence of the acid dissociation constants of chloroquine
    • Ferrari V., Cutler D.J. Temperature dependence of the acid dissociation constants of chloroquine. J. Pharm. Sci. 1987, 76:554-556.
    • (1987) J. Pharm. Sci. , vol.76 , pp. 554-556
    • Ferrari, V.1    Cutler, D.J.2
  • 10
    • 84962467391 scopus 로고    scopus 로고
    • Theoretical calculations of acid dissociation constants: A review
    • Alongi K.S., Shields G.C. Theoretical calculations of acid dissociation constants: A review. Annu. Rep. Comput. Chem. 2010, 6:113-138.
    • (2010) Annu. Rep. Comput. Chem. , vol.6 , pp. 113-138
    • Alongi, K.S.1    Shields, G.C.2
  • 11
    • 75249088152 scopus 로고    scopus 로고
    • A reliable and efficient first-principles-based method for predicting pKa values
    • 1. Methodology, 425-431; 2. Organic Acids, 432-442
    • Zhang S., Baker J., Pulay P. A reliable and efficient first-principles-based method for predicting pKa values. J. Phys. Chem. A 2010, 114. 1. Methodology, 425-431; 2. Organic Acids, 432-442.
    • (2010) J. Phys. Chem. A , vol.114
    • Zhang, S.1    Baker, J.2    Pulay, P.3
  • 12
    • 1642535349 scopus 로고    scopus 로고
    • First-principle predictions of absolute pKa's of organic acids in dimethyl sulfoxide solution
    • Fu Y., Liu L., Li R.-Q., Lui R., Guo Q.-X. First-principle predictions of absolute pKa's of organic acids in dimethyl sulfoxide solution. J. Am. Chem. Soc. 2004, 126:814-822.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 814-822
    • Fu, Y.1    Liu, L.2    Li, R.-Q.3    Lui, R.4    Guo, Q.-X.5
  • 13
    • 5344262585 scopus 로고
    • Molecular structure-property relationships
    • Seybold P.G., May M., Bagal U.A. Molecular structure-property relationships. J. Chem. Educ. 1987, 64:575-581.
    • (1987) J. Chem. Educ. , vol.64 , pp. 575-581
    • Seybold, P.G.1    May, M.2    Bagal, U.A.3
  • 16
    • 0001321370 scopus 로고
    • QSPR: The correlation and quantitative prediction of chemical and physical properties from structure
    • Katritzky A.R., Lobanov V.S., Karelson M. QSPR: The correlation and quantitative prediction of chemical and physical properties from structure. Chem. Soc. Rev. 1995, 24:279-287.
    • (1995) Chem. Soc. Rev. , vol.24 , pp. 279-287
    • Katritzky, A.R.1    Lobanov, V.S.2    Karelson, M.3
  • 17
    • 0002905234 scopus 로고    scopus 로고
    • Structurally diverse quantitative structure-property relationship correlations of technologically relevant physical properties
    • Katritzky A.R., Maran U., Lobanov V.S., Karelson M. Structurally diverse quantitative structure-property relationship correlations of technologically relevant physical properties. J. Chem. Inf. Comput. Sci. 2000, 40:1-18.
    • (2000) J. Chem. Inf. Comput. Sci. , vol.40 , pp. 1-18
    • Katritzky, A.R.1    Maran, U.2    Lobanov, V.S.3    Karelson, M.4
  • 18
    • 77958029276 scopus 로고    scopus 로고
    • Correlation of physical and chemical properties with chemical structure: Utility for prediction
    • Katritzky A.R., Kuanar M., Slavov S., Hall C.D., Karelson M., Kahn I., Dobchev D.A. Correlation of physical and chemical properties with chemical structure: Utility for prediction. Chem. Rev. 2010, 110:5714-5789.
    • (2010) Chem. Rev. , vol.110 , pp. 5714-5789
    • Katritzky, A.R.1    Kuanar, M.2    Slavov, S.3    Hall, C.D.4    Karelson, M.5    Kahn, I.6    Dobchev, D.A.7
  • 19
    • 0038282314 scopus 로고    scopus 로고
    • Theoretical property predictions
    • Livingstone D.J. Theoretical property predictions. Curr. Top. Med. Chem. 2003, 3:1171-1192.
    • (2003) Curr. Top. Med. Chem. , vol.3 , pp. 1171-1192
    • Livingstone, D.J.1
  • 20
    • 84856275825 scopus 로고    scopus 로고
    • Modern methods for estimation of ionization constants of organic compounds in solution
    • Zevatskii Yu.E., Samoilov D.V. Modern methods for estimation of ionization constants of organic compounds in solution. Russ. J. Org. Chem. 2011, 47:1423-1444.
    • (2011) Russ. J. Org. Chem. , vol.47 , pp. 1423-1444
    • Zevatskii, Y.1    Samoilov, D.V.2
  • 21
    • 0024034894 scopus 로고
    • Molecular modeling of the physical properties of the alkanes
    • Needham D.E., Wei I.-C., Seybold P.G. Molecular modeling of the physical properties of the alkanes. J. Am. Chem. Soc. 1988, 110:4186-4194.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 4186-4194
    • Needham, D.E.1    Wei, I.-C.2    Seybold, P.G.3
  • 22
    • 0034779722 scopus 로고    scopus 로고
    • Molecular structure-property relationships for alkenes
    • Nelson S.D., Seybold P.G. Molecular structure-property relationships for alkenes. J. Mol. Graph. Mod. 2001, 20:36-53.
    • (2001) J. Mol. Graph. Mod. , vol.20 , pp. 36-53
    • Nelson, S.D.1    Seybold, P.G.2
  • 23
    • 0040694711 scopus 로고
    • A simple model for the chromatographic retentions of polyhalogenated biphenyls
    • Seybold P.G., Bertrand J. A simple model for the chromatographic retentions of polyhalogenated biphenyls. Anal. Chem. 1993, 65:1631-1634.
    • (1993) Anal. Chem. , vol.65 , pp. 1631-1634
    • Seybold, P.G.1    Bertrand, J.2
  • 24
    • 46149141366 scopus 로고
    • Solvatochromism and thermochromism of rhodamine solutions
    • Hinckley D.A., Seybold P.G., Borris D.P. Solvatochromism and thermochromism of rhodamine solutions. Spectrochim. Acta 1986, 42A:747-754.
    • (1986) Spectrochim. Acta , vol.42 A , pp. 747-754
    • Hinckley, D.A.1    Seybold, P.G.2    Borris, D.P.3
  • 25
    • 45549110735 scopus 로고
    • A Spectroscopic/thermodynamic study of the rhodamine B lactone=zwitterion equilibrium
    • Hinckley D.A., Seybold P.G. A Spectroscopic/thermodynamic study of the rhodamine B lactone=zwitterion equilibrium. Spectrochim. Acta 1988, 44A:1053-1059.
    • (1988) Spectrochim. Acta , vol.44 A , pp. 1053-1059
    • Hinckley, D.A.1    Seybold, P.G.2
  • 26
    • 0023790133 scopus 로고
    • Modeling the tissue solubilities and metabolic rate constant Vmax of halogenated methanes, ethanes, and ethylenes
    • Gargas M.L., Seybold P.G., Andersen M.E. Modeling the tissue solubilities and metabolic rate constant Vmax of halogenated methanes, ethanes, and ethylenes. Toxicol. Lett. 1988, 43:235-256.
    • (1988) Toxicol. Lett. , vol.43 , pp. 235-256
    • Gargas, M.L.1    Seybold, P.G.2    Andersen, M.E.3
  • 27
    • 0032617960 scopus 로고    scopus 로고
    • Explorations of molecular structure-property relationships
    • Seybold P.G. Explorations of molecular structure-property relationships. SAR QSAR Environ. Res. 1999, 10:101-115.
    • (1999) SAR QSAR Environ. Res. , vol.10 , pp. 101-115
    • Seybold, P.G.1
  • 28
    • 0001728908 scopus 로고    scopus 로고
    • Quantum-chemical descriptors in QSAR/QSPR studies
    • Karelson M., Lobanov V.S., Katritzky A.R. Quantum-chemical descriptors in QSAR/QSPR studies. Chem. Rev. 1996, 96:1027-1043.
    • (1996) Chem. Rev. , vol.96 , pp. 1027-1043
    • Karelson, M.1    Lobanov, V.S.2    Katritzky, A.R.3
  • 29
    • 0017913240 scopus 로고
    • Correlation of an Electronic Reactivity Index with Carcinogenicity in Polycyclic Aromatic Hydrocarbons
    • Berger G.D., Smith I.A., Seybold P.G., Serve M.P. Correlation of an Electronic Reactivity Index with Carcinogenicity in Polycyclic Aromatic Hydrocarbons. Tetrahedron Lett. 1978, 231-234.
    • (1978) Tetrahedron Lett. , pp. 231-234
    • Berger, G.D.1    Smith, I.A.2    Seybold, P.G.3    Serve, M.P.4
  • 30
    • 0018165744 scopus 로고
    • Relationships between carcinogenicity and theoretical reactivity indices in polycyclic aromatic hydrocarbons
    • Smith I.A., Berger G.D., Seybold P.G., Serve M.P. Relationships between carcinogenicity and theoretical reactivity indices in polycyclic aromatic hydrocarbons. Cancer Res. 1978, 38:2968-2977.
    • (1978) Cancer Res. , vol.38 , pp. 2968-2977
    • Smith, I.A.1    Berger, G.D.2    Seybold, P.G.3    Serve, M.P.4
  • 31
    • 84987111319 scopus 로고
    • A molecular orbital study of the metabolism and carcinogenecity of the phenols of benzo(a)pyrene
    • Seybold P.G., Gräslund A. A molecular orbital study of the metabolism and carcinogenecity of the phenols of benzo(a)pyrene. Int. J. Quantum Chem. QBS 1980, 7:261-270.
    • (1980) Int. J. Quantum Chem. QBS , vol.7 , pp. 261-270
    • Seybold, P.G.1    Gräslund, A.2
  • 32
    • 84864335517 scopus 로고
    • Steric and electronic determinants of carcinogenicity in polycyclic aromatic hydrocarbons
    • Battelle Press, Columbus, M. Cooke, A.J. Dennis (Eds.)
    • Seybold P.G. Steric and electronic determinants of carcinogenicity in polycyclic aromatic hydrocarbons. Polynuclear Aromatic Hydrocarbons: Chemistry, Characterization and Carcinogenesis 1986, 839-854. Battelle Press, Columbus. M. Cooke, A.J. Dennis (Eds.).
    • (1986) Polynuclear Aromatic Hydrocarbons: Chemistry, Characterization and Carcinogenesis , pp. 839-854
    • Seybold, P.G.1
  • 33
    • 33747866218 scopus 로고
    • Some relations between reaction rates and equilibrium constants
    • Hammett L.P. Some relations between reaction rates and equilibrium constants. Chem. Rev. 1935, 35:125-136.
    • (1935) Chem. Rev. , vol.35 , pp. 125-136
    • Hammett, L.P.1
  • 34
    • 0002801544 scopus 로고
    • The effect of structure upon the reaction of organic compounds. Benzene derivatives
    • Hammett L.P. The effect of structure upon the reaction of organic compounds. Benzene derivatives. J. Am. Chem. Soc. 1937, 59:96-103.
    • (1937) J. Am. Chem. Soc. , vol.59 , pp. 96-103
    • Hammett, L.P.1
  • 35
    • 0000519497 scopus 로고
    • Linear free energy relationships in rate and equilibria phenomena
    • Hammett L.P. Linear free energy relationships in rate and equilibria phenomena. Trans. Faraday Soc. 1938, 156-165.
    • (1938) Trans. Faraday Soc. , pp. 156-165
    • Hammett, L.P.1
  • 37
    • 4243664295 scopus 로고
    • A Survey of Hammett Substituent Constants and Resonance and Field Parameters
    • Hansch C., Leo A., Taft R.W. A Survey of Hammett Substituent Constants and Resonance and Field Parameters. Chem. Rev. 1991, 91:165-195.
    • (1991) Chem. Rev. , vol.91 , pp. 165-195
    • Hansch, C.1    Leo, A.2    Taft, R.W.3
  • 38
    • 0000788692 scopus 로고
    • Free energy relationships from rates of esterification and hydrolysis of aliphatic and ortho-substituted benzoate esters
    • Taft R.W. Free energy relationships from rates of esterification and hydrolysis of aliphatic and ortho-substituted benzoate esters. J. Am. Chem. Soc. 1952, 74:2729-2732.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 2729-2732
    • Taft, R.W.1
  • 39
    • 33947453229 scopus 로고
    • Polar and steric substituent constants for aliphatic and o-benzoate groups from rates of esterification and hydrolysis of esters
    • Taft R.W. Polar and steric substituent constants for aliphatic and o-benzoate groups from rates of esterification and hydrolysis of esters. J. Am. Chem. Soc. 1952, 74:3120-3128.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 3120-3128
    • Taft, R.W.1
  • 40
    • 0000758102 scopus 로고
    • Linear steric energy relationships
    • Taft R.W. Linear steric energy relationships. J. Am. Chem. Soc. 1953, 75:4538-4539.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 4538-4539
    • Taft, R.W.1
  • 41
    • 26844528154 scopus 로고
    • Correlation of the base strengths of amines
    • Hall H.K. Correlation of the base strengths of amines. J. Am. Chem. Soc. 1957, 79:5441-5444.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 5441-5444
    • Hall, H.K.1
  • 42
    • 0041305313 scopus 로고
    • Field and inductive effects on the base strengths of amines
    • Hall H.K. Field and inductive effects on the base strengths of amines. J. Am. Chem. Soc. 1956, 78:2570-2572.
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 2570-2572
    • Hall, H.K.1
  • 43
    • 0001411292 scopus 로고
    • Acid Ionization constants of alcohols. II. Acidities of some substituted methanols and related compounds
    • Ballinger P., Long F.A. Acid Ionization constants of alcohols. II. Acidities of some substituted methanols and related compounds. J. Am. Chem. Soc. 1960, 82:795-798.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 795-798
    • Ballinger, P.1    Long, F.A.2
  • 44
    • 0012281305 scopus 로고
    • Prediction of pKa values
    • Marcel Dekker, New York, S.H. Yalkowsky, A.A. Sinkula, S.C. Valvani (Eds.)
    • Perrin D.D. Prediction of pKa values. Physical Chemical Properties of Drugs 1980, Marcel Dekker, New York. S.H. Yalkowsky, A.A. Sinkula, S.C. Valvani (Eds.).
    • (1980) Physical Chemical Properties of Drugs
    • Perrin, D.D.1
  • 45
    • 0034323922 scopus 로고    scopus 로고
    • Substituent effects on the physical properties and pKa of aniline
    • Gross K.C., Seybold P.G. Substituent effects on the physical properties and pKa of aniline. Int. J. Quantum Chem. 2000, 80:1107-1115.
    • (2000) Int. J. Quantum Chem. , vol.80 , pp. 1107-1115
    • Gross, K.C.1    Seybold, P.G.2
  • 46
    • 0035914103 scopus 로고    scopus 로고
    • Comparison of quantum chemical parameters and Hammett constants in correlating pKa values of substituted anilines
    • Gross K.C., Seybold P.G., Peralta-Inga Z., Murray J.S., Politzer P. Comparison of quantum chemical parameters and Hammett constants in correlating pKa values of substituted anilines. J. Org. Chem. 2001, 66:6919-6925.
    • (2001) J. Org. Chem. , vol.66 , pp. 6919-6925
    • Gross, K.C.1    Seybold, P.G.2    Peralta-Inga, Z.3    Murray, J.S.4    Politzer, P.5
  • 47
    • 0035890870 scopus 로고    scopus 로고
    • Substituent effects on the physical properties and pKa of phenol
    • Gross K.C., Seybold P.G. Substituent effects on the physical properties and pKa of phenol. Int. J. Quantum Chem. 2001, 85:569-579.
    • (2001) Int. J. Quantum Chem. , vol.85 , pp. 569-579
    • Gross, K.C.1    Seybold, P.G.2
  • 48
    • 0037111965 scopus 로고    scopus 로고
    • Substituent effects on the electronic structure and pKa of benzoic acid
    • Hollingsworth C.A., Seybold P.G., Hadad C.M. Substituent effects on the electronic structure and pKa of benzoic acid. Int. J. Quantum Chem. 2002, 90:1396-1403.
    • (2002) Int. J. Quantum Chem. , vol.90 , pp. 1396-1403
    • Hollingsworth, C.A.1    Seybold, P.G.2    Hadad, C.M.3
  • 49
    • 0345472119 scopus 로고
    • Correlation of Hammett's σ-values with electron densities calculated by molecular orbital theory
    • Jaffe H.H. Correlation of Hammett's σ-values with electron densities calculated by molecular orbital theory. J. Chem. Phys. 1952, 20:279-284.
    • (1952) J. Chem. Phys. , vol.20 , pp. 279-284
    • Jaffe, H.H.1
  • 50
    • 2442439484 scopus 로고
    • Theoretical considerations concerning Hammett's equation. II. Calculation of σ-values for toluene and naphthalene
    • Jaffe H.H. Theoretical considerations concerning Hammett's equation. II. Calculation of σ-values for toluene and naphthalene. J. Chem. Phys. 1952, 20:778-780.
    • (1952) J. Chem. Phys. , vol.20 , pp. 778-780
    • Jaffe, H.H.1
  • 51
    • 0008926315 scopus 로고
    • Theoretical considerations concerning Hammett's equation. III. σ-Values for pyridine and other Aza-substituted hydrocarbons
    • Jaffe H.H. Theoretical considerations concerning Hammett's equation. III. σ-Values for pyridine and other Aza-substituted hydrocarbons. J. Chem. Phys. 1952, 20:1554-1555.
    • (1952) J. Chem. Phys. , vol.20 , pp. 1554-1555
    • Jaffe, H.H.1
  • 52
    • 0000109766 scopus 로고
    • Direct prediction of linear free energy substituent effects from 3D structures using comparative molecular field analysis. 1. Electronic effects of substituted benzoic acids
    • Kim K.H., Martin Y.C. Direct prediction of linear free energy substituent effects from 3D structures using comparative molecular field analysis. 1. Electronic effects of substituted benzoic acids. J. Org. Chem. 1991, 56:2723-2729.
    • (1991) J. Org. Chem. , vol.56 , pp. 2723-2729
    • Kim, K.H.1    Martin, Y.C.2
  • 54
    • 84988113034 scopus 로고
    • Correlation analysis of substituent effects on the acidity of benzoic acids by the AM1 method
    • Sotomatsu T., Murata Y., Fujita T. Correlation analysis of substituent effects on the acidity of benzoic acids by the AM1 method. J. Comput. Chem. 1988, 10:94-98.
    • (1988) J. Comput. Chem. , vol.10 , pp. 94-98
    • Sotomatsu, T.1    Murata, Y.2    Fujita, T.3
  • 55
    • 20844460406 scopus 로고    scopus 로고
    • Estimation of Hammett sigma constants of substituted benzenes through accurate density-functional calculation of core-electron binding energy shifts
    • Takahar Y., Chong D.P. Estimation of Hammett sigma constants of substituted benzenes through accurate density-functional calculation of core-electron binding energy shifts. Int. J. Quantum Chem. 2005, 103:509-515.
    • (2005) Int. J. Quantum Chem. , vol.103 , pp. 509-515
    • Takahar, Y.1    Chong, D.P.2
  • 56
    • 0001310740 scopus 로고
    • Calculated electrostatic potentials and local surface ionization energies of para-substituted anilines as measures of substituent effects
    • Haeberlein M., Murray J.S., Brinck T., Politzer P. Calculated electrostatic potentials and local surface ionization energies of para-substituted anilines as measures of substituent effects. Can. J. Chem. 1992, 70:2209-2214.
    • (1992) Can. J. Chem. , vol.70 , pp. 2209-2214
    • Haeberlein, M.1    Murray, J.S.2    Brinck, T.3    Politzer, P.4
  • 57
    • 84864330288 scopus 로고    scopus 로고
    • Sparc On-line Calculator.
    • Sparc On-line Calculator. http://ibmlc2.chem.uga.edu/sparc.
  • 58
    • 0030353420 scopus 로고    scopus 로고
    • Estimation of the Ionization pKa of Pharmaceutical Substances Using the Computer Program SPARC
    • Hilal S.H., El-Shabrawy Y., Carreira L.A., Karickhoff S.W., Toubar S.S., Rizk M. Estimation of the Ionization pKa of Pharmaceutical Substances Using the Computer Program SPARC. Talanta 1996, 43:607-619.
    • (1996) Talanta , vol.43 , pp. 607-619
    • Hilal, S.H.1    El-Shabrawy, Y.2    Carreira, L.A.3    Karickhoff, S.W.4    Toubar, S.S.5    Rizk, M.6
  • 59
    • 84864338184 scopus 로고    scopus 로고
    • Advanced Chemistry Development, Inc.
    • Advanced Chemistry Development, Inc. http://www.acdlabs.com/products.
  • 60
    • 73349118457 scopus 로고    scopus 로고
    • Comparison of nine programs predicting pKa values of pharmaceutical substances
    • Liao C., Nicklaus M.C. Comparison of nine programs predicting pKa values of pharmaceutical substances. J. Chem. Inf. Model. 2009, 49:2801-2812.
    • (2009) J. Chem. Inf. Model. , vol.49 , pp. 2801-2812
    • Liao, C.1    Nicklaus, M.C.2
  • 61
    • 78649513581 scopus 로고    scopus 로고
    • Comparative analysis of QSAR Models for Predicting pKa of organic oxygen acids and nitrogen bases from molecular structure
    • Yu H., Kühne R., Ebert R.-U., Schüürmann G. Comparative analysis of QSAR Models for Predicting pKa of organic oxygen acids and nitrogen bases from molecular structure. J. Chem. Inf. Model. 2010, 50:1949-1960.
    • (2010) J. Chem. Inf. Model. , vol.50 , pp. 1949-1960
    • Yu, H.1    Kühne, R.2    Ebert, R.-U.3    Schüürmann, G.4
  • 63
    • 0024841682 scopus 로고
    • Quantum-mechanically calculated properties for the development of quantitative structure-activity relationships (QSAR's). pKa-values of phenols and aromatic and aliphatic carboxylic acids
    • Grüber C., Bub V. Quantum-mechanically calculated properties for the development of quantitative structure-activity relationships (QSAR's). pKa-values of phenols and aromatic and aliphatic carboxylic acids. Chemosphere 1989, 19:1595-1609.
    • (1989) Chemosphere , vol.19 , pp. 1595-1609
    • Grüber, C.1    Bub, V.2
  • 64
    • 0032890374 scopus 로고    scopus 로고
    • Estimating the pKa of phenols, carboxylic acids and alcohols from semi-empirical quantum chemical methods
    • Citra M.J. Estimating the pKa of phenols, carboxylic acids and alcohols from semi-empirical quantum chemical methods. Chemosphere 1999, 38:191-206.
    • (1999) Chemosphere , vol.38 , pp. 191-206
    • Citra, M.J.1
  • 65
    • 11744331329 scopus 로고
    • Estimation of pKa for organic oxyacids using calculated atomic charges
    • Dixon S.L., Jurs P. Estimation of pKa for organic oxyacids using calculated atomic charges. J. Comput. Chem. 1993, 14:1460-1467.
    • (1993) J. Comput. Chem. , vol.14 , pp. 1460-1467
    • Dixon, S.L.1    Jurs, P.2
  • 67
    • 0036854264 scopus 로고    scopus 로고
    • Estimation of pKa using semiempirical molecular orbital methods. Part 2. Application to amines, anilines, and various nitrogen containing heterocyclic compounds
    • Tehan B.G., Lloyd E.J., Wong M.G., Pitt W.R., Montana J.G., Gancia E., Manallack D.T. Estimation of pKa using semiempirical molecular orbital methods. Part 2. Application to amines, anilines, and various nitrogen containing heterocyclic compounds. Quant. Struct. Act. Relat. 2002, 21:473-485.
    • (2002) Quant. Struct. Act. Relat. , vol.21 , pp. 473-485
    • Tehan, B.G.1    Lloyd, E.J.2    Wong, M.G.3    Pitt, W.R.4    Montana, J.G.5    Gancia, E.6    Manallack, D.T.7
  • 68
    • 55349095068 scopus 로고    scopus 로고
    • Analysis of the pKas of aliphatic amines using quantum chemical descriptors
    • Seybold P.G. Analysis of the pKas of aliphatic amines using quantum chemical descriptors. Int. J. Quantum Chem. 2008, 108:2849-2855.
    • (2008) Int. J. Quantum Chem. , vol.108 , pp. 2849-2855
    • Seybold, P.G.1
  • 69
    • 80054014157 scopus 로고    scopus 로고
    • A class project combining organic chemistry, quantum chemistry, and statistics
    • Simons M., Topper A., Southerland B., Seybold P.G. A class project combining organic chemistry, quantum chemistry, and statistics. Annu. Rep. Comput. Chem. 2011, 7:237-249.
    • (2011) Annu. Rep. Comput. Chem. , vol.7 , pp. 237-249
    • Simons, M.1    Topper, A.2    Southerland, B.3    Seybold, P.G.4
  • 70
    • 34247255912 scopus 로고    scopus 로고
    • Estimation of pKa for druglike compounds using semiempirical and information-based descriptors
    • Jelfs S., Ertl P., Selzer P. Estimation of pKa for druglike compounds using semiempirical and information-based descriptors. J. Chem. Inf. Model. 2007, 47:450-459.
    • (2007) J. Chem. Inf. Model. , vol.47 , pp. 450-459
    • Jelfs, S.1    Ertl, P.2    Selzer, P.3
  • 71
    • 33845768501 scopus 로고    scopus 로고
    • Prediction of pKa values for aliphatic carboxylic acids and alcohols with empirical atomic charge descriptors
    • Zhang J., Kleinöder T., Gasteiger J. Prediction of pKa values for aliphatic carboxylic acids and alcohols with empirical atomic charge descriptors. J. Chem. Inf. Model. 2006, 46:2256-2266.
    • (2006) J. Chem. Inf. Model. , vol.46 , pp. 2256-2266
    • Zhang, J.1    Kleinöder, T.2    Gasteiger, J.3
  • 72
    • 49149147973 scopus 로고
    • Iterative partial equalization of orbital electronegativity-A rapid access to atomic charges
    • Gasteiger J., Marsili M. Iterative partial equalization of orbital electronegativity-A rapid access to atomic charges. Tetrahedron 1980, 36:3219-3228.
    • (1980) Tetrahedron , vol.36 , pp. 3219-3228
    • Gasteiger, J.1    Marsili, M.2
  • 73
    • 0037026962 scopus 로고    scopus 로고
    • Comparison of different atomic charge schemes for predicting pKa variations in substituted anilines and phenols
    • Gross K.C., Seybold P.G., Hadad C.M. Comparison of different atomic charge schemes for predicting pKa variations in substituted anilines and phenols. Int. J. Quantum Chem. 2002, 90:445-458.
    • (2002) Int. J. Quantum Chem. , vol.90 , pp. 445-458
    • Gross, K.C.1    Seybold, P.G.2    Hadad, C.M.3
  • 75
    • 84986492477 scopus 로고
    • Atomic charges derived from semiempirical methods
    • Besler B.H., Merz K.M., Kollman P.A. Atomic charges derived from semiempirical methods. J. Comput. Chem. 1990, 11:431-439.
    • (1990) J. Comput. Chem. , vol.11 , pp. 431-439
    • Besler, B.H.1    Merz, K.M.2    Kollman, P.A.3
  • 76
    • 33845185172 scopus 로고
    • A new population analysis based on atomic polar tensors
    • Cioslowski J. A new population analysis based on atomic polar tensors. J. Am. Chem. Soc. 1989, 111:8333-8336.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8333-8336
    • Cioslowski, J.1
  • 77
    • 36849131708 scopus 로고
    • Criteria for the construction of good self-consistent-field molecular orbital wave functions, and the significance of LCAO-MO population analysis
    • Mulliken R.S. Criteria for the construction of good self-consistent-field molecular orbital wave functions, and the significance of LCAO-MO population analysis. J. Chem. Phys. 1962, 36:3428.
    • (1962) J. Chem. Phys. , vol.36 , pp. 3428
    • Mulliken, R.S.1
  • 79
    • 4243333196 scopus 로고
    • On the Nonorthoganality Problem
    • Löwdin P.-O. On the Nonorthoganality Problem. Adv. Quantum Chem. 1970, 5:185-199.
    • (1970) Adv. Quantum Chem. , vol.5 , pp. 185-199
    • Löwdin, P.-O.1
  • 82
    • 0003138066 scopus 로고
    • An ab initio LCAO-MO study of the substituent effect in benzenoid systems: meta- and para-Substituted benzoic acids
    • Böhm S., Kuthan J. An ab initio LCAO-MO study of the substituent effect in benzenoid systems: meta- and para-Substituted benzoic acids. Int. J. Quantum Chem. 1984, 26:21-33.
    • (1984) Int. J. Quantum Chem. , vol.26 , pp. 21-33
    • Böhm, S.1    Kuthan, J.2
  • 83
    • 73049111151 scopus 로고    scopus 로고
    • Correlations between quantum chemical indices and the pKas of a diverse set of organic phenols
    • Kreye W.C., Seybold P.G. Correlations between quantum chemical indices and the pKas of a diverse set of organic phenols. Int. J. Quantum Chem. 2009, 109:3679-3684.
    • (2009) Int. J. Quantum Chem. , vol.109 , pp. 3679-3684
    • Kreye, W.C.1    Seybold, P.G.2
  • 84
    • 0000235295 scopus 로고    scopus 로고
    • Assessment of a new local exchange functional OPTX
    • Hoe W.-M., Cohen A.J., Handy N.C. Assessment of a new local exchange functional OPTX. Chem. Phys. Lett. 2001, 341:319-328.
    • (2001) Chem. Phys. Lett. , vol.341 , pp. 319-328
    • Hoe, W.-M.1    Cohen, A.J.2    Handy, N.C.3
  • 85
    • 84961980743 scopus 로고
    • COSMO: A new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient
    • Klamt A., Schüürmann G. COSMO: A new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc. Perkin Trans. 1993, 2:799-805.
    • (1993) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 799-805
    • Klamt, A.1    Schüürmann, G.2
  • 87
    • 37049101326 scopus 로고
    • Theoretical correlation of substituent effects on the acidity of benzoic acids in the vapor phase
    • La Manna G., Tschinke V., Paolini L. Theoretical correlation of substituent effects on the acidity of benzoic acids in the vapor phase. J. Chem. Soc. Perkin trans. II 1985, 1393-1394.
    • (1985) J. Chem. Soc. Perkin trans. II , pp. 1393-1394
    • La Manna, G.1    Tschinke, V.2    Paolini, L.3
  • 88
    • 7944220743 scopus 로고
    • Relationships between the HOMO energies and pKa values in monocyclic and bicyclic azines
    • Soscún Machado H.J., Hinchliffe A. Relationships between the HOMO energies and pKa values in monocyclic and bicyclic azines. J. Mol. Struct. (THEOCHEM) 1995, 339:255-258.
    • (1995) J. Mol. Struct. (THEOCHEM) , vol.339 , pp. 255-258
    • Soscún Machado, H.J.1    Hinchliffe, A.2
  • 89
    • 77956688253 scopus 로고    scopus 로고
    • Average local ionization energies: Significance and applications
    • Elsevier, Amsterdam, C. Parkanyi (Ed.)
    • Murray J.S., Politzer P. Average local ionization energies: Significance and applications. Theoretical Organic Chemistry 1998, Elsevier, Amsterdam. C. Parkanyi (Ed.).
    • (1998) Theoretical Organic Chemistry
    • Murray, J.S.1    Politzer, P.2
  • 91
    • 4544228375 scopus 로고    scopus 로고
    • Relationships Between aqueous acidities and computed surface-electrostatic potentials and local ionization energies of substituted phenols and benzoic acids
    • Ma Y., Gross K.C., Hollingsworth C.A., Seybold P.G., Murray J.S. Relationships Between aqueous acidities and computed surface-electrostatic potentials and local ionization energies of substituted phenols and benzoic acids. J. Mol. Mod. 2004, 10:235-239.
    • (2004) J. Mol. Mod. , vol.10 , pp. 235-239
    • Ma, Y.1    Gross, K.C.2    Hollingsworth, C.A.3    Seybold, P.G.4    Murray, J.S.5
  • 92
    • 14544306424 scopus 로고    scopus 로고
    • Theoretical study of hydrogen-bonded complexes of chlorophenols with water or ammonia: Correlations and predictions of pKa values
    • Han J., Deming R.L., Tao F.-M. Theoretical study of hydrogen-bonded complexes of chlorophenols with water or ammonia: Correlations and predictions of pKa values. J. Phys. Chem. A 2005, 109:1159-1167.
    • (2005) J. Phys. Chem. A , vol.109 , pp. 1159-1167
    • Han, J.1    Deming, R.L.2    Tao, F.-M.3
  • 93
    • 21644477186 scopus 로고    scopus 로고
    • Molecular structures and properties of the complete series of bromophenols: Density functional theory calculations
    • Han J., Lee H., Tao F.-M. Molecular structures and properties of the complete series of bromophenols: Density functional theory calculations. J. Phys. Chem. A 2005, 109:5186-5192.
    • (2005) J. Phys. Chem. A , vol.109 , pp. 5186-5192
    • Han, J.1    Lee, H.2    Tao, F.-M.3
  • 94
    • 31144439102 scopus 로고    scopus 로고
    • Correlations and predictions of pKa values for fluorophenols and bromophenols using hydrogen-bonded complexes with ammonia
    • Han J., Tao F.-M. Correlations and predictions of pKa values for fluorophenols and bromophenols using hydrogen-bonded complexes with ammonia. J. Phys. Chem. A 2006, 110:257-263.
    • (2006) J. Phys. Chem. A , vol.110 , pp. 257-263
    • Han, J.1    Tao, F.-M.2
  • 95
    • 84962408511 scopus 로고    scopus 로고
    • Correlations and predictions of carboxylic acid pKa values using intermolecular structure and properties of hydrogen-bonded complexes
    • Tao L., Han J., Tao F.-M. Correlations and predictions of carboxylic acid pKa values using intermolecular structure and properties of hydrogen-bonded complexes. J. Phys. Chem. A 2008, 112:775-782.
    • (2008) J. Phys. Chem. A , vol.112 , pp. 775-782
    • Tao, L.1    Han, J.2    Tao, F.-M.3
  • 97
    • 55549093137 scopus 로고    scopus 로고
    • Acidity of meta- and para-substituted aromatic acids: A conceptual DFT study
    • Gupta K., Giri S., Chattaraj P.K. Acidity of meta- and para-substituted aromatic acids: A conceptual DFT study. New J. Chem. 2008, 32:1945-1952.
    • (2008) New J. Chem. , vol.32 , pp. 1945-1952
    • Gupta, K.1    Giri, S.2    Chattaraj, P.K.3
  • 99
    • 0038443475 scopus 로고    scopus 로고
    • Substructure versus whole-molecule approaches for calculating log P
    • Mannhold R., Petrauskas A. Substructure versus whole-molecule approaches for calculating log P. QSAR Comb. Sci. 2003, 22:466-475.
    • (2003) QSAR Comb. Sci. , vol.22 , pp. 466-475
    • Mannhold, R.1    Petrauskas, A.2
  • 100
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer R.D., Patterson D.E., Bunce J.D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110:5959-5967.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5959-5967
    • Cramer, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 101
    • 0032723279 scopus 로고    scopus 로고
    • Application of Multivariate data analysis methods to comparative molecular field analysis (CoMFA) data: Proton affinities and pKa prediction for nucleic acids components
    • Gargallo R., Sotriffer C.A., Liedl K.R., Rode B.M. Application of Multivariate data analysis methods to comparative molecular field analysis (CoMFA) data: Proton affinities and pKa prediction for nucleic acids components. J. Comput. Aided Mol. Des. 1999, 13:611-623.
    • (1999) J. Comput. Aided Mol. Des. , vol.13 , pp. 611-623
    • Gargallo, R.1    Sotriffer, C.A.2    Liedl, K.R.3    Rode, B.M.4
  • 102
    • 0036628547 scopus 로고    scopus 로고
    • Novel methods for the prediction of log P, pKa, and log D
    • Xing L., Glen R.C. Novel methods for the prediction of log P, pKa, and log D. J. Chem. Inf. Comput. Sci. 2002, 42:796-805.
    • (2002) J. Chem. Inf. Comput. Sci. , vol.42 , pp. 796-805
    • Xing, L.1    Glen, R.C.2
  • 103
    • 0042292781 scopus 로고
    • Partial least-squares method for spectrofluorometric analysis of mixtures of humic acid and ligninsulfonate
    • Lindberg W., Persson J.-Å., Wold S. Partial least-squares method for spectrofluorometric analysis of mixtures of humic acid and ligninsulfonate. Anal. Chem. 1983, 55:643-648.
    • (1983) Anal. Chem. , vol.55 , pp. 643-648
    • Lindberg, W.1    Persson, J.-Å.2    Wold, S.3
  • 104
    • 0038512085 scopus 로고    scopus 로고
    • Predicting pKa by molecular tree structured fingerprints and PLS
    • Xing L., Glen R.C., Clark R.D. Predicting pKa by molecular tree structured fingerprints and PLS. J. Chem. Inf. Comput. Sci. 2003, 43:870-879.
    • (2003) J. Chem. Inf. Comput. Sci. , vol.43 , pp. 870-879
    • Xing, L.1    Glen, R.C.2    Clark, R.D.3
  • 105
    • 56449089334 scopus 로고    scopus 로고
    • PKa prediction of monoprotic small molecules the SMARTS way
    • Lee A.C., Yu J.-Y., Crippen G.M. pKa prediction of monoprotic small molecules the SMARTS way. J. Chem. Inf. Model. 2008, 48:2042-2053.
    • (2008) J. Chem. Inf. Model. , vol.48 , pp. 2042-2053
    • Lee, A.C.1    Yu, J.-Y.2    Crippen, G.M.3
  • 106
    • 24044549995 scopus 로고    scopus 로고
    • Prediction of pKa for neutral and basic drugs based on radial basis function neural networks and the heuristic method
    • Luan F., Ma W., Zhang H., Zhang X., Liu M., Hu Z., Fan B. Prediction of pKa for neutral and basic drugs based on radial basis function neural networks and the heuristic method. Pharm. Res. 2005, 22:1454-1460.
    • (2005) Pharm. Res. , vol.22 , pp. 1454-1460
    • Luan, F.1    Ma, W.2    Zhang, H.3    Zhang, X.4    Liu, M.5    Hu, Z.6    Fan, B.7
  • 107
    • 58549107560 scopus 로고    scopus 로고
    • Application of principal component-genetic algorithm-artificial neural network for prediction acidity constant of various nitrogen-containing compounds in water
    • Habibi-Yangjeh A., Pourbasheer E., Danandeeh-Jenagharad M. Application of principal component-genetic algorithm-artificial neural network for prediction acidity constant of various nitrogen-containing compounds in water. Monatsh. Chem. 2009, 140:15-27.
    • (2009) Monatsh. Chem. , vol.140 , pp. 15-27
    • Habibi-Yangjeh, A.1    Pourbasheer, E.2    Danandeeh-Jenagharad, M.3
  • 108
  • 109
    • 79951824875 scopus 로고    scopus 로고
    • Practical calculation of molecular acidity with the aid of a reference molecule
    • Burger S.K., Liu S., Ayers P.W. Practical calculation of molecular acidity with the aid of a reference molecule. J. Phys. Chem. A 2011, 115:1293-1304.
    • (2011) J. Phys. Chem. A , vol.115 , pp. 1293-1304
    • Burger, S.K.1    Liu, S.2    Ayers, P.W.3
  • 111
    • 33748905333 scopus 로고    scopus 로고
    • Model for aqueous solvation based on class iv atomic charges and first solvation shell effects
    • Chambers C.C., Hawkins G.D., Cramer C.J., Truhlar D.G. Model for aqueous solvation based on class iv atomic charges and first solvation shell effects. J. Phys. Chem. 1996, 100:16385-16398.
    • (1996) J. Phys. Chem. , vol.100 , pp. 16385-16398
    • Chambers, C.C.1    Hawkins, G.D.2    Cramer, C.J.3    Truhlar, D.G.4
  • 112
    • 84962385262 scopus 로고    scopus 로고
    • Self-consistent reaction field model for aqueous and nonaqueous solutions based on accurate polarized partial charge models
    • Marenich A.V., Olson R.M., Kelly C.P., Cramer C.J., Truhlar D.J. Self-consistent reaction field model for aqueous and nonaqueous solutions based on accurate polarized partial charge models. J. Chem. Theory Comput. 2007, 3:2011-2033.
    • (2007) J. Chem. Theory Comput. , vol.3 , pp. 2011-2033
    • Marenich, A.V.1    Olson, R.M.2    Kelly, C.P.3    Cramer, C.J.4    Truhlar, D.J.5
  • 113
    • 79958043256 scopus 로고    scopus 로고
    • PKa prediction from an ab initio Bond Length: Part 2-Phenols
    • Harding A.P., Popelier P.L.A. pKa prediction from an ab initio Bond Length: Part 2-Phenols. Phys. Chem. Chem. Phys. 2011, 13:11264-11282.
    • (2011) Phys. Chem. Chem. Phys. , vol.13 , pp. 11264-11282
    • Harding, A.P.1    Popelier, P.L.A.2
  • 114
    • 33745597056 scopus 로고    scopus 로고
    • AM1: A reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I
    • Rocha G.B., Freire R.O., Simas A.M., Stewart J.J.P. AM1: A reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I. J. Comput. Chem. 2006, 27:1101-1111.
    • (2006) J. Comput. Chem. , vol.27 , pp. 1101-1111
    • Rocha, G.B.1    Freire, R.O.2    Simas, A.M.3    Stewart, J.J.P.4
  • 115
    • 0001576358 scopus 로고
    • Family-independent relationships between computed molecular surface quantities and solute hydrogen bond acidity/basicity and solute-induced methanol O-H infrared frequency shifts
    • Hagelin H., Murray J.S., Brinck T., Berthelot M., Politzer P. Family-independent relationships between computed molecular surface quantities and solute hydrogen bond acidity/basicity and solute-induced methanol O-H infrared frequency shifts. Can. J. Chem. 1995, 73:483-488.
    • (1995) Can. J. Chem. , vol.73 , pp. 483-488
    • Hagelin, H.1    Murray, J.S.2    Brinck, T.3    Berthelot, M.4    Politzer, P.5
  • 116
    • 69549086566 scopus 로고    scopus 로고
    • PKa prediction from "Quantum Chemical Topology" descriptors
    • Harding A.P., Wedge D.C., Popelier P.L.A. pKa prediction from "Quantum Chemical Topology" descriptors. J. Chem. Inf. Model. 2009, 49:1914-1924.
    • (2009) J. Chem. Inf. Model. , vol.49 , pp. 1914-1924
    • Harding, A.P.1    Wedge, D.C.2    Popelier, P.L.A.3
  • 117
    • 0344887064 scopus 로고
    • Equilibrium acidities in dimethyl sulfoxide solution
    • Bordwell F.G. Equilibrium acidities in dimethyl sulfoxide solution. Acc. Chem. Res. 1988, 21:456-463.
    • (1988) Acc. Chem. Res. , vol.21 , pp. 456-463
    • Bordwell, F.G.1
  • 118
    • 0001561187 scopus 로고
    • Acid ionization constants of alcohols. I. Trifluoroethanol in the solvents H2O and D2O
    • Ballinger P., Long F.A. Acid ionization constants of alcohols. I. Trifluoroethanol in the solvents H2O and D2O. J. Am. Chem. Soc. 1959, 81:1050-1053.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 1050-1053
    • Ballinger, P.1    Long, F.A.2
  • 119
    • 0000026284 scopus 로고
    • Comparison of substituent effects on dissociation and conjugation of phenols with those of carboxylic acids in acetonitrile, N,N-dimethylformamide, and dimethyl sulfoxide
    • Chantooni M.K., Kolthoff I.M. Comparison of substituent effects on dissociation and conjugation of phenols with those of carboxylic acids in acetonitrile, N,N-dimethylformamide, and dimethyl sulfoxide. J. Phys. Chem. 1976, 80:1306-1310.
    • (1976) J. Phys. Chem. , vol.80 , pp. 1306-1310
    • Chantooni, M.K.1    Kolthoff, I.M.2
  • 122
    • 0000164572 scopus 로고
    • Acidity measurements in THF: V. Heteroaromatic compounds containing 5-membered rings
    • Fraser R.R., Mansour T.S., Savard S. Acidity measurements in THF: V. Heteroaromatic compounds containing 5-membered rings. Can. J. Chem. 1985, 63:3505-3509.
    • (1985) Can. J. Chem. , vol.63 , pp. 3505-3509
    • Fraser, R.R.1    Mansour, T.S.2    Savard, S.3
  • 123
    • 0001030014 scopus 로고
    • Equilibria involving organic anions in dimethyl sulfoxide and N-methylpyrrolidin-2-one: Acidities, ion pairing, and hydrogen bonding
    • Bordwell F.G., Branca J.C., Hughes D.L., Olmstead W.N. Equilibria involving organic anions in dimethyl sulfoxide and N-methylpyrrolidin-2-one: Acidities, ion pairing, and hydrogen bonding. J. Org. Chem. 1980, 45:3305-3313.
    • (1980) J. Org. Chem. , vol.45 , pp. 3305-3313
    • Bordwell, F.G.1    Branca, J.C.2    Hughes, D.L.3    Olmstead, W.N.4
  • 124
    • 0001601489 scopus 로고
    • The relative acidity of water, methanol, and other weak acids in isopropyl alcohol solution
    • Hine J., Hine M. The relative acidity of water, methanol, and other weak acids in isopropyl alcohol solution. J. Am. Chem. Soc. 1952, 74:5266-5271.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 5266-5271
    • Hine, J.1    Hine, M.2
  • 125
    • 33845277980 scopus 로고
    • Structural and solvent effects evaluated from acidities measured in dimethyl sulfoxide and in the gas phase
    • Taft R.W., Bordwell F.G. Structural and solvent effects evaluated from acidities measured in dimethyl sulfoxide and in the gas phase. Acc. Chem. Res. 1988, 21:463-469.
    • (1988) Acc. Chem. Res. , vol.21 , pp. 463-469
    • Taft, R.W.1    Bordwell, F.G.2
  • 126
    • 0001644701 scopus 로고
    • Prediction, parsimony, and noise
    • Gauch H.C. Prediction, parsimony, and noise. Am. Sci. 1993, 81:468-478.
    • (1993) Am. Sci. , vol.81 , pp. 468-478
    • Gauch, H.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.