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Correlation analysis in the chemistry of free radicals

Artem Rafaelovich Cherkasov 1
Artem Rafaelovich Cherkasov
, 
Mats Jonsson 2
Mats Jonsson
, 
Vladimir Ivanovich Galkin 1
Vladimir Ivanovich Galkin
, 
Rafael Askhatovich Cherkasov 1
Rafael Askhatovich Cherkasov
1 Department of Chemistry, Kazan State University
2 Department of Chemistry, Royal Institute of Technology, Stockholm, Sweden
10.1070/RC2001v070n01ABEH000574
Published 30 November 2000
Communication , Volume 70, Issue 1, 1-22
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Cherkasov A. R. et al. Correlation analysis in the chemistry of free radicals // Russian Chemical Reviews. 2001. Vol. 70. No. 1. pp. 1-22.
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Cherkasov A. R., Jonsson M., Galkin V. I., Cherkasov R. A. Correlation analysis in the chemistry of free radicals // Russian Chemical Reviews. 2001. Vol. 70. No. 1. pp. 1-22.
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TY - JOUR
DO - 10.1070/RC2001v070n01ABEH000574
UR - https://rcr.colab.ws/publications/10.1070/RC2001v070n01ABEH000574
TI - Correlation analysis in the chemistry of free radicals
T2 - Russian Chemical Reviews
AU - Cherkasov, Artem Rafaelovich
AU - Jonsson, Mats
AU - Galkin, Vladimir Ivanovich
AU - Cherkasov, Rafael Askhatovich
PY - 2001
DA - 2000/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 1-22
IS - 1
VL - 70
ER -
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@article{2001_Cherkasov,
author = {Artem Rafaelovich Cherkasov and Mats Jonsson and Vladimir Ivanovich Galkin and Rafael Askhatovich Cherkasov},
title = {Correlation analysis in the chemistry of free radicals},
journal = {Russian Chemical Reviews},
year = {2001},
volume = {70},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2001v070n01ABEH000574},
number = {1},
pages = {1--22},
doi = {10.1070/RC2001v070n01ABEH000574}
}
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Cherkasov, Artem Rafaelovich, et al. “Correlation analysis in the chemistry of free radicals.” Russian Chemical Reviews, vol. 70, no. 1, Nov. 2001, pp. 1-22. https://rcr.colab.ws/publications/10.1070/RC2001v070n01ABEH000574.
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Abstract

Published data now available on the use of correlation analysis in free-radical chemistry are discussed systematically. The scales of 'radical' σ-constants of substituents proposed previously are analysed. It is shown that none of them is applicable as a general scale because almost in all cases, it is impossible to separate correctly the proper radical and polar contributions to the overall effect of substituents. A new approach to the quantitative estimation of the relationship between the structure and reactivity of molecules in free-radical processes called r–2-analysis is proposed. The bibliography includes 238 references.

References

2.
Reactions of thiocyanogen and thiocyanogen halides with unsaturated compounds
Skorobogatova E.V., Kartashov V.R.
Russian Chemical Reviews , 1998
3.
The concept of electronegativity. The current state of the problem
Cherkasov A.R., Galkin V.I., Zueva E.M., Cherkasov R.A.
Russian Chemical Reviews , 1998
5.
The problem of the quantitative evaluation of the inductive effect: correlation analysis
Cherkasov A.R., Galkin V.I., Cherkasov R.A.
Russian Chemical Reviews , 1996
6.
Inductive substituent effects
Galkin V.I.
Journal of Physical Organic Chemistry , 1999
7.
The inductive effect - the present position
Exner O., Charton M., Galkin V.
Journal of Physical Organic Chemistry , 1999
12.
Homolytic Abstraction of Benzylic Hydrogen
Gilliom R.D., Ward B.F.
Journal of the American Chemical Society , 1965
13.
REACTIONS OF ALKOXY RADICALS: I. HYDROGEN ATOM ABSTRACTION FROM SUBSTITUTED TOLUENES
Kennedy B.R., Ingold K.U.
Canadian Journal of Chemistry , 1966
15.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
25.
The Mechanism of Benzylic Bromination with N-Bromosuccinimide
Pearson R.E., Martin J.C.
Journal of the American Chemical Society , 1963
26.
Polar effects in radical reactions. IV. Nucleophilic character of the 3-heptyl radical
Henderson R.W.
Journal of the American Chemical Society , 1975
31.
Electrophilic Substituent Constants
Brown H.C., Okamoto Y.
Journal of the American Chemical Society , 1958
33.
Relative Reactivities of Substituted Toluenes Toward Trichloromethyl Radicals
Huyser E.S.
Journal of the American Chemical Society , 1960
36.
Remote substituent effects on polar and non-polar covalent bonds
Jonsson M., Lind J., Merényi G., Eriksen T.E.
Journal of the Chemical Society Perkin Transactions 2 , 1994
38.
Redox chemistry of substituted benzenes: the one-electron reduction potentials of methoxy-substituted benzene radical cations
Jonsson M., Lind J., Reitberger T., Eriksen T.E., Merenyi G.
The Journal of Physical Chemistry , 1993
39.
Redox and Acidity Properties of 4-Substituted Aniline Radical Cations in Water
Jonsson M., Lind J., Eriksen T.E., Merenyi G.
Journal of the American Chemical Society , 1994
40.
N–H bond dissociation energies, reduction potentials and pKas of multisubstituted anilines and aniline radical cations
Jonsson M., Lind J., Merényi G., Eriksen T.E.
Journal of the Chemical Society Perkin Transactions 2 , 1995
41.
Redox properties of 4-substituted aryl methyl chalcogenides in water
Jonsson M., Lind J., Merényi G., Eriksen T.E.
Journal of the Chemical Society Perkin Transactions 2 , 1995
44.
Linear Free Energy Relationships.
Wells P.R.
Chemical Reviews , 1963
47.
Relative reactivities in vinyl copolymerization
Alfrey T., Price C.C.
Journal of Polymer Science , 1947
48.
The Reactivities of Nuclear-Substituted Phenyl Methacrylates in Radical Copolymerization with Styrene
Otsu T., Ito T., Fujii Y., Imoto M.
Bulletin of the Chemical Society of Japan , 1968
49.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
51.
An improved σ· scale. The thermal decomposition of substituted dibenzylmercury compounds in alkane solutions
Dinçtürk S., Jackson R.A., Townson M.
Journal of the Chemical Society Chemical Communications , 1979
52.
Free radical reactions in solution. Part 6. Thermal decomposition of substituted dibenzyl mercurials in solution. An improved σ˙ scale
Dinçtürk S., Jackson R.A., Townson M., Aǧirbaş H., Billingham N.C., March G.
Journal of the Chemical Society Perkin Transactions 2 , 1981
53.
Free radical reactions in solution. Part 9. Further σ˙ values from decomposition of substituted dibenzylmercurials
Aǧirbas H., Jackson R.A.
Journal of the Chemical Society Perkin Transactions 2 , 1983
60.
Copolymerization. X. The Effect of meta- and para-Substitution on the Reactivity of the Styrene Double Bond
Walling C., Briggs E.R., Wolfstirn K.B., Mayo F.R.
Journal of the American Chemical Society , 1948
61.
Hammett Relationship in Radical Reactions
OTSU T., YAMAMOTO T.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1965
64.
SIGMA VALUES FROM REACTIVITIES1
Taft R.W.
The Journal of Physical Chemistry , 1960
66.
Exner O., Lakomý J.
Collection of Czechoslovak Chemical Communications , 2012
67.
Kalfus K., Večeřa M., Exner O.
Collection of Czechoslovak Chemical Communications , 2012
69.
The Substituent Effect. X. Solvolysis of 3- and 4-Substituted 1-(1-Naphthylethyl) Chlorides
Tsuno Y., Sawada M., Fujii T., Yukawa Y.
Bulletin of the Chemical Society of Japan , 1975
70.
Field and resonance components of substituent effects
Swain C.G., Lupton E.C.
Journal of the American Chemical Society , 1968
71.
Substituent Effects. I. Introduction
Dewar M.J., Grisdale P.J.
Journal of the American Chemical Society , 1962
72.
Steric effects. I. Esterification and acid-catalyzed hydrolysis of esters
Charton M.
Journal of the American Chemical Society , 1975
73.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
74.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
75.
On the nature of the phenylazo group
Fisher T.H., Meierhoefer A.W.
Tetrahedron , 1975
76.
Meta-substituent effects on benzyl free-radical stability
Fisher T.H., Dershem S.M., Prewitt M.L.
Journal of Organic Chemistry , 1990
78.
Free radical reactions in solution
El-Durini N.M., Jackson R.A.
Journal of Organometallic Chemistry , 1982
79.
Free radical reactions in solution. Part 3. The decomposition of dibenzylmercury in toluene
Jackson R.A., O'Neill D.W.
Journal of the Chemical Society Perkin Transactions 2 , 1978
83.
The effect of the diethylphosphonate group on free radical stabilities
Creary X., Benage B., Mehrsheikh-Mohammadi M.E., Bays J.P.
Tetrahedron Letters , 1985
87.
An Elimination-Addition Route to Substituted Methylenecyclopropanes
Shields T.C., Shoulders B.A., Krause J.F., Osborn C.L., Gardner P.D.
Journal of the American Chemical Society , 1965
89.
Partial asymmetric synthesis of methylenecyclopropanes and spiropentanes
Noyori R., Takaya H., Nakanisi Y., Nozaki H.
Canadian Journal of Chemistry , 1969
90.
Degeneracy in the methylenecyclopropane rearrangement
Gilbert J.C., Butler J.R.
Journal of the American Chemical Society , 1970
93.
Thermal rearrangement of 1-alkoxy-2-methylenecyclopropanes
Kirmse W., Murawski H.
Journal of the Chemical Society Chemical Communications , 1977
97.
Substituent effects and free radical stability. The methoxy group
Timberlake J.W., Hodges M.L.
Tetrahedron Letters , 1970
98.
Free radical-substituent effects (II); steric effects and sulfur participation
Timberlake J.W., Garner A.W., Hodges M.L.
Tetrahedron Letters , 1973
99.
Substituent effects in radical reactions. III. Thermolysis of substituted phenylazomethanes, 3,5-diphenyl-1-pyrazolines, and azopropanes
Bandlish B.K., Garner A.W., Hodges M.L., Timberlake J.W.
Journal of the American Chemical Society , 1975
100.
Radical stabilizing effects
Dube M.F., Timberlake J.W.
Tetrahedron , 1980
102.
Radical Stabilization and Ground State Polar Substituent Effects in the Thermal Decomposition of Azoalkanes
Nau W.M., Harrer H.M., Adam W.
Journal of the American Chemical Society , 1994
104.
Chemistry of diarylazoalkanes. II. Effect of para-substituents on the thermal decomposition of azocumenes
Shelton J.R., Liang C.K., Kovacic P.
Journal of the American Chemical Society , 1968
105.
Chemistry of diarylazoalkanes. III. Effect of structural variation on rate and nature of the thermal decomposition
Kovacic P., Flynn R.R., Gormish J.F., Kappelman A.H., Shelton J.R.
Journal of Organic Chemistry , 1969
110.
Sterically hindered free radicals. 18. Stabilization of free radicals by substituents as studied by using triphenylmethyls
Neumann W.P., Penenory A., Stewen U., Lehnig M.
Journal of the American Chemical Society , 1989
113.
115
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1957
114.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
116.
Stabilization of benzylic radicals by substituents: an EPR study of para-substituted benzyl radicals
Jackson R.A., Sharifi M.
Journal of the Chemical Society Perkin Transactions 2 , 1996
117.
A Correlation of Reaction Rates
Hammond G.S.
Journal of the American Chemical Society , 1955
119.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
122.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
129.
A Theoretical Approach to Substituent Interactions in Substituted Benzenes
Pross A., Radom L.
Progress in Physical Organic Chemistry , 1981
130.
Correlation analysis of electron spin resonance spectra: the a-spectrum
Jackson R.A.
Journal of the Chemical Society Perkin Transactions 2 , 1983
131.
Objective analysis of EPR spectra by computer methods
Jackson R.A.
Journal of the Chemical Society Perkin Transactions 2 , 1993
132.
Substituent Effects on the Zero‐Field Splitting Parameters of Localized Triplet, 1,3‐Cyclopentanediyl Biradicals
Adam W., Fröhlich L., Nau W.M., Korth H., Sustmann R.
Angewandte Chemie - International Edition , 1993
134.
About monoradicals, triplet diradicals and higher spin states: Understanding electronic substituent effects through EPR and time-resolved UV spectroscopy
Adam W., van Barneveld C., Emmert O., Harrer H.M., Kita F., Kumar A.S., Maas W., Nau W.M., Reddy S.H., Wirz J.
Pure and Applied Chemistry , 1997
135.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
137.
Spin control in organic molecules
Dougherty D.A.
Accounts of Chemical Research , 1991
138.
III - Bond energies
Benson S.W.
Journal of Chemical Education , 1965
139.
141
Friedl.
141.
Heats of formation of gaseous free radicals via ion cyclotron double resonance spectroscopy
DeFrees D.J., McIver R.T., Hehre W.J.
Journal of the American Chemical Society , 1980
142.
Hydrocarbon Bond Dissociation Energies
McMillen D.F., Golden D.M.
Annual Review of Physical Chemistry , 1982
143.
Estimation of bond dissociation energies, including DH°(RSCH2–H), from barriers to internal rotation
Nonhebel D.C., Walton J.C.
Journal of the Chemical Society Chemical Communications , 1984
145.
C−H Bond Dissociation Energies of Alkyl Amines: Radical Structures and Stabilization Energies§
Wayner D.D., Clark K.B., Rauk A., Yu D., Armstrong D.A.
Journal of the American Chemical Society , 1997
146.
Three methods to measure RH bond energies
Berkowitz J., Ellison G.B., Gutman D.
The Journal of Physical Chemistry , 1994
147.
The C–H Bond Energy in Toluene and Xylenes
Szwarc M.
Journal of Chemical Physics , 1948
151.
From equilibrium acidites to radical stabilization energies
Bordwell F.G., Zhang X.M.
Accounts of Chemical Research , 1993
152.
154
Friedl.
156.
Substituent effects on the strength of single bonds and in free-radical chemistry
Leroy G., Sana M., Wilante C.
Journal of Molecular Structure THEOCHEM , 1990
157.
Steric and electronic substituent effects on the carbon-carbon bond
Rüchardt C., Beckhaus H.
Topics in Current Chemistry , 1986
158.
Stability of chemical species
Leroy G.
International Journal of Quantum Chemistry , 1983
159.
A theoretical investigation of the properties of free radicals.
Leroy G.
Journal of Molecular Structure THEOCHEM , 1983
162.
Thermochemical Stability of α-Amino-α-carbonylmethyl Radicals and Their Resonance As Measured by ESR
Welle F.M., Beckhaus H., Rüchardt C.
Journal of Organic Chemistry , 1997
164.
Are relative bond energies a measure of radical stabilization energies?
Clark K.B., Wayner D.D.
Journal of the American Chemical Society , 1991
165.
Energies of Activation. The Paradigm of Hydrogen Abstractions by Radicals
Zavitsas A.A., Chatgilialoglu C.
Journal of the American Chemical Society , 1995
166.
168
1918
168.
Stabilization energies and structures of substituted methyl radicals
Pasto D.J., Krasnansky R., Zercher C.
Journal of Organic Chemistry , 1987
169.
171
Friedl.
170.
A MNDO study of the structures and stabilities of some substituted pentadienyl anions
Dewar M.J., Fox M.A., Nelson D.J.
Journal of Organometallic Chemistry , 1980
171.
Improved radical stabilization energies
Lehd M., Jensen F.
Journal of Organic Chemistry , 1991
174.
Substituent Effects on the C−H Bond Dissociation Energy of Toluene. A Density Functional Study
Wu Y., Wong C., Chan K.W., Ji G., Jiang X.
Journal of Organic Chemistry , 1996
175.
Molecular orbital theory of the electronic structure of organic compounds. V. Molecular theory of bond separation
Hehre W.J., Ditchfield R., Radom L., Pople J.A.
Journal of the American Chemical Society , 1970
177.
Effects of adjacent acceptors and donors on the stabilities of carbon-centered radicals
Bordwell F.G., Zhang X., Alnajjar M.S.
Journal of the American Chemical Society , 1992
179.
181
Chem. Abs. , 1947
180.
182
1947
181.
A comment on monomer reactivity indices for copolymerization
Cammarata A., Yau S.J.
Journal of Polymer Science Part A-1 Polymer Chemistry , 1970
183.
The thermal isomerization of 1.2-dimethyl cyclo propane I. Cis-trans isomerization
Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences , 1960
184.
The Racemization of trans-1,2-Divinylcyclopropane
Arai M., Crawford R.J.
Canadian Journal of Chemistry , 1972
185.
Thermal rearrangement of alkoxycyclopropanes
Kirmse W., Zeppenfeld M.
Journal of the Chemical Society Chemical Communications , 1977
186.
A Molecular Orbital Theory of Organic Chemistry. IV.1 Free Radicals
Dewar M.J.
Journal of the American Chemical Society , 1952
187.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
189.
Merostabilisation — A New Principle Governing the Stability of Organic Free Radicals
Bettinetti G., W. Baldock R., Hudson P., R. Katritzky A., Soti F.
Heterocycles , 1973
190.
Stable free radicals. Part I. A new principle governing the stability of organic free radicals
Baldock R.W., Hudson P., Katritzky A.R., Soti F.
Journal of the Chemical Society Perkin Transactions 1 , 1974
191.
Stable free radicals. Part II. Some substituted pyridinyls
Katritzky A.R., Soti F.
Journal of the Chemical Society Perkin Transactions 1 , 1974
192.
Stabilization of Radicals by “Capto‐Dative” Substitution ? C ? C Addition to Radicophilic Olefins
Stella L., Janousek Z., Merényi R., Viehe H.G.
Angewandte Chemie - International Edition , 1978
193.
Capto‐dative Substituent Effects in Syntheses with Radicals and Radicophiles [New synthetic methods (32)]
Viehe H.G., Merényi R., Stella L., Janousek Z.
Angewandte Chemie - International Edition , 1979
194.
Capto-dative substituent effects—VIII
Mignani S., Beaujean M., Janousek Z., Merenyi R., Viehe H.G.
Tetrahedron , 1981
196.
198
W. Cohen
Rec. Trav. chim. , 1919
197.
Captodative substituent effects—XV
Mignani S., Merényi R., Janousek Z., Viehe H.G.
Tetrahedron , 1985
198.
Preparative trapping of tert-butoxy radicals by captodative olefins
Mignani S., Janousek Z., Merenyi R., Viehe H.G., Riga J., Verbist J.
Tetrahedron Letters , 1984
199.
Kinetic effects in radical addition reactions to radicophiles
Lahousse F., Merényi R., Desmurs J.R., Allaime H., Borghese A., Viehe H.G.
Tetrahedron Letters , 1984
200.
Captodative substituent effects — Part XXXI olefins with captodative substitution in [2+2] cycloadditions
De Cock C., Piettre S., Lahousse F., Janousek Z., Merényi R., Viehe H.G.
Tetrahedron , 1985
202.
The Structure of Anemonin
Moriarty R.M., Romain C.R., Karle I.L., Karle J.
Journal of the American Chemical Society , 1965
203.
205
N. Bunge
Zhur. Russ. Fiz.-Khim. Obshch. , 1889
204.
Acceptor, donor, and captodative stabilization in transition states of 5-hexen-1-yl radical cyclizations
Park S.U., Chung S.K., Newcomb M.
Journal of the American Chemical Society , 1986
205.
The preparation of capto-dative radicals by homosolvolysis
Singh H., Tedder J.M.
Journal of the Chemical Society Chemical Communications , 1980
206.
Silyl-substituted cyclopropyl carbenoids
Creary X., Jiang Z., Butchko M., McLean K.
Tetrahedron Letters , 1996
207.
Capto-dative substituent effect on the cis-trans isomerisation of cyclopropanes
De Mesmaeker A., Vertommen L., Merényl R., Viehe H.G.
Tetrahedron Letters , 1982
209.
Allylic radicals with captodative substitution : Easy homolysis of 1,5-hexadienes.
Van Hoecke M., Borghese A., Penelle J., Merényi R., Viehe H.G.
Tetrahedron Letters , 1986
210.
Capto-Dative (cd) Radical Stabilisation: Kinetics of the Isomerisation of p-Substituted α Cyano-, α Methyl Benzyl Radical Dimers
Merenyi R., Daffe V., Klein J., Masamba W., Viehe H.G.
Bulletin des Sociétés Chimiques Belges , 2010
212.
Capto-dative stabilisation in amino-substituted radicals
MacInnes I., Walton J.C., Nonhebel D.C.
Journal of the Chemical Society Chemical Communications , 1985
213.
The captodative effect
Viehe H.G., Janousek Z., Merenyi R., Stella L.
Accounts of Chemical Research , 1985
215.
A theoretical investigation of the structure and reactivity of carbon-centred radicals
Leroy G., Peeters D.
Journal of Molecular Structure THEOCHEM , 1981
216.
A quantitative assessment of the merostabilization energy of carbon-centered radicals
Katritzky A.R., Zerner M.C., Karelson M.M.
Journal of the American Chemical Society , 1986
218.
Absolute rates for dimerization of capto-dative substituted methyl radicals in solution: absence of kinetic stabilization
Korth H., Sustmann R., Merényi R., Viehe H.G.
Journal of the Chemical Society Perkin Transactions 2 , 1983
220.
Birkhofer H., Hädrich J., Beckhaus H., Rüchardt C.
1987
222.
224
Chem. Abs. , 1959
223.
A new approach to the theoretical estimation of inductive constants
Cherkasov A.R., Galkin V.I., Cherkasov R.A.
Journal of Physical Organic Chemistry , 1998
224.
226
Chem. Abs. , 1961
225.
227
B. Roetheke
1958
226.
228
B. Roetheke
Chem. Abs. , 1959
227.
229
1959
228.
230
Chem. Abs. , 1962
229.
“Inductive” electronegativity scale
Cherkasov A.R., Galkin V., Cherkasov R.
Journal of Molecular Structure THEOCHEM , 1999
230.
“Inductive” electronegativity scale: 2. ‘Inductive’ analog of chemical hardness
Cherkasov A.R., Galkin V., Cherkasov R.
Journal of Molecular Structure THEOCHEM , 2000
233.
235
R. Peffen
1967
234.
Substituent Effects on Thermochemical Properties of Free Radicals. New Substituent Scales for C-Centered Radicals
Cherkasov A., Jonsson M.
Journal of Chemical Information and Computer Sciences , 1998
236.
238
Brown G P
Am. Chem. Soc., Polymer Preprints , 1964
237.
Linear Steric Energy Relationships
Taft R.W.
Journal of the American Chemical Society , 1953
238.
Persistent carbon-centered radicals
Griller D., Ingold K.U.
Accounts of Chemical Research , 1976
239.
A New Method for Estimation of Homolytic C−H Bond Dissociation Enthalpies
Cherkasov A., Jonsson M.
Journal of Chemical Information and Computer Sciences , 2000