Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf
STATISTICS A: TABLES AND GRAPHS © Dr. John Andraos, 2000 - 2008 Department of Chemistry, York University 4700 Keele Street, Toronto, ONTARIO M3J 1P3, CANADA For suggestions, corrections, additional information, and comments please send e-mails to
[email protected]
http://www.chem.yorku.ca/NAMED/
Contents: (1) Fundamental Ideas in Chemistry (2) Timeline of Ideas in Chemistry (3) Concepts in Chemistry Not Named After People (4) Concepts in Physical Organic Chemistry (5) Named Laboratory Apparatus (6) Named Organic Reactions (7) Named Reagents, Catalysts, and Compounds
1
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf
(1) Fundamental Ideas in Chemistry Nationality American American-born British German French Canadians Russian Austrian Dutch Swedish Swiss Danish Hungarian Polish Irish Japanese Italian Latvian Mexican Egyptian China Czech Estonian Indian Norwegian TOTAL
Number of Scientists 121 84 63 55 28 16 13 12 11 10 10 7 5 4 3 3 3 2 1 1 1 2 1 1 1 457
2
Nationality Norwegian
Indian
Estonian
Czech
China
Egyptian
Mexican
Latvian
Italian
Japanese
Irish
Polish
Hungarian
Danish
Swiss
Swedish
Dutch
Russian
Austrian
Canadians
French
German
British
American-born
American
Number of Scientists
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 3
Fundamental Chemistry Concepts and Equations: Demography
120
100
80
60
40
20
0
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf
4
(2) Timeline of Ideas in Chemistry
Contributions to Chemistry Timeline: Named Concepts
80
Number of Concepts Not Named After People
70
Number of Concepts Named After People
60 50 40 30 20 10
Decade
1991 - 2000
1971 - 1980
1951 - 1960
1931 - 1940
1911 - 1920
1891 - 1900
1871 - 1880
1851 - 1860
1831 - 1840
1811 - 1820
1791 - 1800
1771 - 1780
1751 - 1760
1731 - 1740
1711 - 1720
1691 - 1700
1671 - 1680
1651 - 1660
0 1631 - 1640
Number of Named Concepts
90
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf
5
CUMULATIVE GROWTH OF DISCOVERIES IN CHEMISTRY & PHYSICS THAT IMPACT CHEMISTRY
500
400
300
200
100
YEAR
1991
1979
1970
1962
1954
1946
1937
1929
1921
1913
1905
1897
1888
1879
1869
1858
1843
1831
1820
1806
1788
1690
0 1637
NUMBER OF DISCOVERIES
600
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf FUNDAMENTAL DEVELOPMENTS BENEFICIAL TO CHEMISTRY: TIMELINE YEAR 1637
CONCEPT Snell's law of refraction
1644
Torricelli barometer
1662 1663
Boyle's law Pascal's law of pressure
1672 1676 1678 1679
Newton (dispersion of light) Mariotte's law Hooke's law Fermat (refraction of light)
1690
Huygens principle
1724 1729
Fahrenheit temperature scale Bouguer's law
1738
Bernoulli (kinetic theory of gases)
1742
Celsius temperature scale
1760
Lambert's law
1775
Lavoisier's law
1787 1788 1788
Charles' law Coulomb's law Blagden's law (freezing point depression)
1791 1791 1799 1800
Galvani (electric current) Prevost theory of exchanges (dynamic equilibrium between cold and hot bodies) Proust's law Voltaic cell
1802 1803 1804 1804 1805 1805 1806 1807 1808 1809
Dalton's law of partial pressures Black (discovery of latent and specific heat) Young (interference of light) Henry's law Dalton's law of multiple proportions Dalton's law of solubility of gases in liquids Grotthuss chain Young's modulus of elasticity Dalton's atomic theory Gay-Lussac's law
1811
Avogadro Law
6
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1812 1817 1819 1820 1820 1820
Mohs hardness scale Fraunhofer diffraction, lines Dulong-Petit law Ampere's law Oersted law (action of currents on magnets) Biot-Savart law
1821 1822 1822 1824 1826 1826 1827 1830
Mitscherlich (law of isomorphism) Seebeck effect Fourier heat theorem Carnot cycle Fresnel (diffraction of light) Ohm's law Brownian motion Hamilton operator
1831 1832 1832 1833 1833 1834 1834 1836 1838 1840
Neumann's law Henry (induction concept) Berzelius (isomerism concept) Graham's law Faraday law Lenz's law Clapeyron equation of state Berzelius/Ostwald (catalysis concept) Miller's law Hess' law
1841 1841 1841 1843 1847 1847 1848 1848 1848 1848 1848 1850
Gauss (magnetic force measurement) Joule's law Grotthuss-Draper law Joule (mechanical equivalent of heat) Helmholtz (conservation of energy) Doppler effect Thomson abolute temperature scale (Kelvin) Pasteur separation of racemic tartrates Kelvin (absolute temperature scale) Kohlrausch current theory Bravais lattices Clausius statement of second law of thermodynamics
1851 1852 1852 1855 1855 1856 1858 1858
Hofmann rule Beer-Lambert-Bouguer law Stokes' law of fluorescence Fick's first and second laws of diffusion Mohr titration Stokes law Kirchhoff's laws (electrolytes) Kirchhoff's law of heat radiation
1863
Mobius strip
7
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1863 1865 1865 1865 1865 1866 1868 1869 1869 1869 1870 1870
Kohlrausch relaxation Joule-Thomson coefficient Kekule structures Maxwell electromagnetic equations Mach bands Loschmidt number Angstrom length Mendeleev's periodic law Tyndall effect Massieu functions Markovnikov rule Lorenz-Lorentz formula
1871 1873 1874 1874 1875 1875 1875 1875 1875 1875 1875 1876 1877 1877 1879 1879 1880
Maxwell's thermodynamic equations van der Waals equation of state van't Hoff-Le Bel asymmetric carbon model McLeod vacuum gauge Berthelot's equation Maxwell-Boltzmann distribution Gibbs equation Gibbs free energy Gibbs phase rule Saytzeff rule Kerr electro-optic effect Viktor Meyer method Kerr magneto-optic effect Van't Hoff's law Stefan law of temperature radiation Hall effect Curie law
1882 1882 1882 1883 1883 1884 1884 1885 1886 1886 1886 1887 1887 1887 1888 1888 1888 1888 1889
Helmholtz equation Raoult's law Carnelley's melting point-molecular symmetry rule Reynolds number Kjeldahl method of nitrogen determination Le Chatelier's principle Van't Hoff equation Balmer series Allihn condenser Gibbs-Duhem equation Tait free path van't Hoff theory of dilute solutions Arrhenius (dissociation of ions in water) Michelson-Morley experiment Ostwald dilution law van't Hoff's law of osmosis Beckmann thermometer, Beckmann method Hofmeister series Arrhenius equation
8
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1889 1890 1890
Nernst equation Rydberg transition Rydberg formula
1891 1893 1893 1893 1894 1895 1895 1895 1895 1895 1896 1896 1897 1897 1900 1900 1900 1900 1900
Fischer projections Walden inversion rule Wien's displacement law Werner (configuration of inorganic compounds) Meyer steric hindrance Roentgen ray Dewar flask Perrin (negative charges in cathode rays) Cotton effect Pulfrich's refractometer Becquerel, Curie (discovery of radioactivity) Fabry-Perot interferometer Zeeman effect Thompson (discovery of electron) Rayleigh-Jeans law Planck's equation, quanta concept Planck's radiation law Larmor precession frequency Meyer-Overton rule, hypothesis, theory, correlation
1901 1903 1904 1904 1905 1905 1906 1906 1906 1907 1908 1908 1908 1908 1908 1908 1908 1909 1909 1910 1910 1910
Pockels effect Thomson model of atom Langevin equation Bravais-Friedel law Friedel's law of rational symmetric intercepts Curie-Weiss law Nernst heat theorem Einstein model Rosanoff-Fischer projection rules Davies condenser Friedel's law of mean indices Paschen's series Vigreux column Haber process Henderson-Hasselbalch equation Ritz principle, procedure Einstein-Smoluchowski equation Sorensen pH scale Geiger counter Hill plot Knudsen vacuum gauge Abderhalden optical method
1911 1911 1912
Gieger-Nuttall law Zeleny electroscope Debye model, T3 law
9
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1912 1912 1912 1912 1912 1912 1913 1913 1913 1913 1913 1913 1913 1913 1914 1914 1916 1916 1916 1917 1917 1918 1918 1919 1919 1920
Einstein law Friedrichs condenser Bragg equation Laue symmetry groups Stark-Einstein law of photochemical equivalence Debye equation Bodenstein steady state approximation Michaelis-Menten equation Moseley's law Bohr model of the atom Gouy-Chapman diffuse double layer Fajan's bonding rules Stark effect Millikan oil drop experiment Lyman series Rutherford scattering Sommerfeld model Lewis structures Ehrenfest adiabatic theorem Smoluchowski equation Thiele tube Madelung series Nernst radical chain Stern-Volmer plot Dufton column Dean-Stark apparatus
1921 1921 1921 1922 1922 1922 1922 1923 1923 1923 1923 1923 1923 1923 1924 1924 1924 1924 1924 1924 1924 1925 1925
Ehrenfest symmetry factor Bohr correspondence principle Lande g-factor Kasha-Vavilov rule Brackett series Stern-Gerlach experiment Townsend effect Auger effect, Auger electron spectroscopy Bronsted catalysis law Bronsted-Lowry acid Debye-Huckel law Lewis acid Compton effect Gaede diffusion pump Bronsted-Bjerrum equation Pauli exclusion principle Pfund series Bredt's rule Bose-Einstein statistics Hanle effect Hudson's rules Pulfrich's photometer de Broglie's law
10
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1925 1925 1925 1925 1925 1925 1925 1926 1926 1926 1926 1926 1927 1927 1927 1927 1927 1927 1927 1927 1928 1928 1928 1928 1928 1928 1929 1929 1930 1930 1930 1930 1930 1930 1930
Ising model Hund's rules Russell-Saunders coupling Briggs-Haldane solution to Michaelis-Menten equation Haworth formulas Paschen-Back effect Laporte rule Guggenheim method Schrodinger equation Fermi-Dirac distribution Wigner's rules Debye-Waller factor Rice-Ramsperger-Kassel (RRK) theory Born-Oppenheimer approximation Heitler-London treatment Heisenberg uncertainty principle Ehrenfest theorem Onsager limiting law Hinshelwood equation Lennard-Jones potential Gamow-Condon-Gurney law Raman spectroscopy Hartree equation Franck-Condon principle Grotrian diagrams Cori cycle Morse potential Slater determinant Slater orbital Haldane equation Haldane relationships Hickman oil diffusion pump London dispersion forces Turner-Czerny optical arrangement Mills-Nixon effect
1931 1931 1931 1931 1931 1931 1932 1932 1932 1932 1932 1932 1932 1932
Huckel molecular orbital theory Jablonski diagram Huckel 4n + 2 rule Onsager reciprocal relations Van de Graaff electrostatic generator Pfeiffer effect Hammett acidity function Pauling electronegativity scale Wigner tunnelling correction van Vleck paramagnetism Hanes-Woolf plot Fenske equation Langmuir adsorption isotherm Langmuir equation
11
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1933 1933 1933 1933 1934 1934 1934 1934 1934 1934 1934 1934 1934 1934 1935 1935 1935 1935 1935 1935 1935 1935 1935 1936 1936 1936 1936 1936 1937 1937 1937 1937 1938 1938 1939 1939 1939 1940
Koopmans theorem Bell equation Hellmann-Feynmann theorem Kapustinskii equation Patterson functions Szilard-Chalmers effect Badger rules and equation Lineweaver-Burk plot Kirkwood-Onsager equation Moller-Plesset single point energy calculation Renner-Teller effect Chadwick (discovery of neutron) Cherenkov effect, radiation Mulliken-Jaffe electronegativity scale Müller-Müller-Rodloff biradical rule Teller-Redlich product rule Baker-Nathan effect Eyring equation Hammett equation Eyring transition state theory Kreb's cycle London equations London equations (superconductivity) Gross-Butler equation Bell-Evans-Polanyi principle Jahn-Teller effect Gamow-Teller selection rule Gray unit of radiation Penning vacuum gauge Krebs cycle Fiegl spot tests Langmuir-Blodgett film Evans-Polanyi relation BET (Brunauer-Emmett-Teller) method Zucker-Hammett hypothesis Evans principle Weibull distribution Pauli principle
1941 1941 1942 1942 1942 1944 1945 1946 1947 1947 1948
Fieser-Woodward rules Stockmayer potential Eadie plot Flory-Huggins theory Wheland intermediate Pirani vacuum gauge Pitzer ring strain Bloch equations Bigeleisen-Wolfsberg equation Bigeleisen-Goepper-Mayer heavy atom approximation Jones effect
12
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1948 1948 1949 1949 1950 1950 1950 1950
Grunwald-Winstein equation Pake pattern Forster cycle Scatchard plot Feynman diagrams Hahn spin echoes Kasha's rule Lowdin orthogonalization
1951 1951 1951 1951 1951 1952 1952 1952 1952 1953 1953 1953 1953 1953 1953 1953 1953 1953 1953 1953 1953 1953 1954 1954 1954 1955 1955 1955 1955 1956 1956 1956 1956 1957 1957 1957 1957 1958 1958 1958 1959
Hartree-Fock-Roothaan theory Cahn-Ingold-Prelog rules Rice-Ramsperger-Kassel-Marcus (RRKM) theory Davydov splitting/exciton theory Dewar-Chatt-Duncanson model Fukui frontier molecular orbital theory Taft equation Dewar PMO method Entner-Doudoroff pathway PPP theory (Pariser-Parr-Pople) Prelog's rules Doering-Zeiss intermediate Dexter excitation transfer Frost polygon Leffler hypothesis Swain-Scott equation Nuclear Overhauser effect Walsh diagrams Shoolery rule Humphreys series Watson-Crick base pairing in DNA Mossbauer spectroscopy Curtin-Hammett principle Carr-Purcell experiment Ramachandran triple helix (collagen) Hammond postulate Newman projection Winstein-Holness equation Mulliken population analysis Edwards equation Marcus equation King-Altman method Calvin cycle BCS (Bardeen-Cooper-Schrieffer) theory of superconductivity Gillespie-Nyholm model Zimmerman-Traxler transition state Allred-Rochow electronegativity scale Kosower Z-values Dirac bracket notation Swain-Schaad equation Hofstee plot
13
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1959 1959 1959 1959 1960 1960 1960
Yukawa-Tsuno equation Karplus equation Cram's rule CPK space filling models (Corey-Pauling-Koltun) Alder rule Berry pseudorotation Wanzlich equilibrium
1961 1961 1961 1961 1962 1962 1963 1963 1963 1963 1963 1963 1963 1963 1964 1965 1966 1966 1966 1966 1966 1967 1968 1968 1969 1969 1969 1969 1969 1970 1970
Marcus-Hush relationship Schenck sensitization mechanism Westheimer principle Dreiding molecular model Hartmann-Hahn experiment Method of Wong and Hanes Schachtschneider method of vibrational frequency calculations Dimroth-Reichardt parameter Pearson's HSAB principle Cleland rules Hoogsteen base pairing Meutterties rule Ramachandran plot Birks scheme for excimer fluorescence Eigen curve Woodward-Hoffmann rules Bunnett-Olsen equations Volkenstein-Goldstein method Dunitz angle Hammond-Herkstroeter plot Feynman ratchet and pawl Verlet algorithm in reaction dynamics Swain-Lupton equation El-Sayed's rule Kaptein-Closs rules Benson's additivity rules Edward-Lemieux effect (anomeric effect) Hansch constant Chauvin-Herisson mechanism More O'Ferrall-Jencks diagram Rehm-Weller equation
1972 1972 1972 1974 1975 1975 1975 1975 1975 1976
Ritchie equation Kaptein's rules Koppel-Palm solvent parameters Cornish-Bowden plot Redfield sequence Sanger method of DNA sequencing Southern blot Tolman cone angle Bordwell carbon acidity scale in polar non-hydrogen-bond solvents Kamlet-Taft solvent parameters
14
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1976 1976 1977 1977 1977 1977 1978
Davydov splitting Baldwin's rules Kaptein-Closs rules Jencks' clock Maxam-Gilbert method of DNA sequencing Topliss decision tree Cox-Yates acidity function
1985 1985 1988 1988 1990
Albery-Siebrand model Maehr stereochemical descriptors Boyd-Edgecombe electronegativity parameters Becke-Lee-Yang-Parr method Lever ligand electrochemical parameters
1991 1997
ZINDO (Zerner-INDO) method Lipinski rule of 5
2001
Little effect
15
(3) Concepts in Chemistry Not Named After People YEAR 1819 1832
1848
CONCEPTS NOT NAMED AFTER PEOPLE Discovery of optical rotation of plane polarized light Concept that green parts of plants absorb carbon dioxide so that light energy is transformed into chemical energy stereochemistry
1850
laws of chemical kinetics
1852 1855 1858 1858 1859
concept of valence actinometry tetravalent nature of carbon Distinction between atoms and molecules Spectra of gases
1860
atomic spectra
1861 1866 1867
1867 1868
SCIENTISTS Biot, J.B. Dutrochet, R.H.
Pasteur, L./van't Hoff, J.H./Le Bel, J.A. van't Hoff, J.H./Wilhelmy, L.F. Frankand, Sir E. Bunsen, R./Roscoe, H. Couper, A.S./Kekuke, A. Cannizzaro, S. Plücker, J./Hittorf, W.
Kirchhoff, G.; Hartley, W.N.; Bunsen, R. forerunner of modern structural formula Loschmidt, J. phosphorescence Sidot, T. law of mass action Waage. P./Guldberg, C./Harcourt, A.V./Esson, W. Doubling of reaction rate with a 10 degree increment Harcourt, A.V. in temperature origin of colour Graebe, C./Liebermann, C./Witt, O.N./Armstrong, H.E.
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf
16
1874 1875
Aromatic substitution Isomer enumeration
1877
tautomerism
1879
ultraviolet spectroscopy
1880 1880
Discovery of isomorphism and polymorphism in crystals Oxidation numbers
1883 1887 1888 1888 1890 1890
catalysis ionization theory law of osmotic pressure Discovery of liquid crystals chair and boat ring conformations Stereoisomerism (existence of stereoisomers)
Ostwald, W. Arrhenius, S. van't Hoff, J.H. Reinitzer, F. Sachse, H./Mohr, E. Meyer, V./ Auwers, K./Eiloart, A.
1891 1894 1894 1896
Villiers, A./Schardinger, F. Werner, A. Meyer, V. Overton, C.E.
1897 1897 1898
Discovery of cyclodextrins co-ordination numbers in inorganic compounds steric effect Active transport of solutes against concentration gradient cell-free fermentation discovery of electron colloids
1899 1900 1900
reaction intermediates concept (carbocations) disintegration of the elements quantum concept
1901 1902 1903
blackbody radiation Planck, M. protein and peptide structure Fischer, E. use of enzymes to catalyze simple organic reactions Acree, S.F./Kastle, J.H./Loevenhart, A.S./Cornforth, J.W./Prelog, V. Transmutation of the elements Brooks, H. infrared spectroscopy Coblentz, W.W. photoelectric effect Einstein, A. Isotope concept Soddy, F. chromatography Tswett, M. liquification of helium Kamerlingh-Onnes, H. alpha particles Rutherford, E. directing groups in aromatic chemistry Holleman, A.F. discovery of sedimentation equilibrium Perrin, J.B.
1904 1905 1905 1905 1906 1908 1909 1910 1910
Koerner, W. Cayley, A./ Crum Brown, A. Laar, C./Butlerov, A./Baeyer, A./Wislicenus, J./Meyer, K.H./Knorr, L./Nef, J.U./Michael, A. Hartley, W.N./Huntington, A.K. Mallard, F.E. Johnson, O.C.
Buchner, E. Thomson, J.J. Zsigmondy, R./Svedberg, T. Stieglitz, J./Norris, J.F. Rutherford, E. Planck, M.
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1911 1911
17
atomic nucleus Discovery of optical activity in co-ordination compounds x-ray diffraction
Rutherford, E. Werner, A./King, V.L.
1920
Laue, M./Bragg, W.L./Bragg, W.H. chemical high pressure methods Bergius, F./Bosch, C. group displacement law Fajans, K.; Soddy, F. radiotracers Paneth, F./Hevesy, G. superconductivity at low temperatures Kamerlingh-Onnes, H. potential energy surfaces Marcelin, R. Experimental verification of tetrahedral asymmetry at Fischer, E. carbon pH indicators Lubs, H.A./Clark, W.M./Acree, S.F. Dipole moment Debye, P. covalent bonding Lewis, G.N. octet rule Lewis, G.N./Langmuir, I. kinetics of adsorption Langmuir, I. mutorotations Hudson, C.S. mass spectrometry Aston, F.W. concept of isosteres Langmuir, I.; Mulliken, R.; Hund, F. hydrogen bonding Latimer, W.H./Rodebush, W.H./Huggins, M.L. Rule of alternating polarities Lapworth,A.
1921
electrophilicity-nucleophilicity
1922
combustion and explosives
1922 1922
polymer chemistry Asymmetric molecule without asymmetric carbon atoms inductive effect
Fry, H.S./Bronsted, J.N./Lowry, T.M./Lapworth, A./Lewis, G.N. Hinshelwood, C.N./Semenov, N.N. Staudinger, H. Christie, G.H./Kenner, J.
1912 1912 1913 1913 1914 1914 1914 1915 1915 1916 1916 1916 1917 1918 1919 1920
1923 1923 1923 1924 1924
vectorial analysis of net dipole moment Connection between SN2 mechanism and Waldon inversion rule electron configuration (aufbau principle) linear free energy relationships
1924
mesomeric (resonance) effect
1924 1925 1925
Concept of isobestic point synthesis of radioactive elements crystal lattice energy
Lewis, G.N./Ingold, C.K./Lowry, T.M. Thomson, J.J. Phillips, H./Kenyon, J. Bohr, N. Bronsted, J.N./Pedersen, K./Hammett, L.P. Lucas, H.J./Arndt, F./Ingold, C.K. Thiel, A./Prideaux, E.B.R. Joliot, F./Joliot-Curie, I. Mayer, J.E.; LennardJones, J.E.
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1926 1926
crystallization of enzymes electron spin
1926 1927 1927
Electronic theory of organic chemistry solvolysis wave nature of electron
1927 1928
discovery of cytochromes electron diffraction by crystals
1928 1929 1929 1930 1930 1930 1930
quantum theory of electron concept of conformation discovery of parahydrogen electrostatic (field) effect microanalytical methods for organic substances development of the cyclotron partition functions
1932 1932 1932 1933 1933 1933 1933
discovery of deuterium protecting groups in organic synthesis discovery of neutron absolute zero measurements atropisomerism Whole number rule for isotopes Three-point model for molecular chiral recognition
1934 1934 1934
hyperconjugation SN1/SN2 synthesis of new radioactive elements using slow neutrons phase contrast microscopy ion exchange resins substituent effect isotopic exchange isotopic labelling experiment
1934 1935 1935 1935 1935
1935 1935 1935 1936 1936 1937 1937 1937 1937 1937
nuclear fission Dipole moment measurements to elucidate stereochemistry Concept of resonance hybrids isotope effect discovery of rotational barrier in ethane chain mechanism (concept of chain transfer and vinyl polymerization kinetics) crossover experiment acidity function condensed matter physics Peroxide effect
18 Sumner, J.B. Uhlenbeck, G./ Goudsmit, S.A. Robinson, R./Ingold, C.K. Ward, A.M./Hammett, L.P. Davisson, C.J./Germer, L.H. Keilin, D. Davisson, C.J./Thomson, G.P. Dirac, P.A.M. Haworth, W.N. Harteck, P. London, F. Pregl, F. Lawrence, E.O. Giauque, W.; Eyring, H.; Halford; Eidenhoff Urey, H.C. Bergmann, M. Chadwick, J. Giauque, W.F. Kuhn, R. Aston, F.W. Easson, E.H./Stedman, E./Ogston, A.G. Wheland, G.W. Ingold, C.K./Hughes, E.D. Fermi, E. Zernike, F. Adams, B.A./Holmes, E.L. Hammett, L.P. Urey, H.C. Urey, H.C./Ingold, C.K./Rittenberg, D./Schoenheimer, R. Hahn, O./Meitner, L. Jensen, K.A. Bury, C.R. Reitz, O. Pitzer, K.S. Flory, P.J. Hurd, C.D. Hammett, L.P. Landau, L.D. Kharash, M.S./Mayo, F.R.
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1938 1939 1939 1939
principle of least motion anchimeric assistance energy production from ATP by enzyme catalysis Effect of resonance on electronic transitions
1939 1940 1940 1940 1940 1940 1940
Electrode kinetics Heterogeneous catalysis Solvent effects in kinetics common ion effect normal salt effect concept of complementariness in biological macromolecules Stopped flow technique
1941 1941
A1 and A2 mechanisms liquid-liquid and gas-liquid chromatography
1941 1944 1944 1944 1945 1946 1946 1947 1948 1948 1949
discovery of carbon-14 B-strain (bond) discovery of streptomycin DNA as source of heredity F-strain (force) nuclear magnetic resonance chain reacting atomic pile electron spin resonance hybridization in chemical bonding E1/E2 eliminations thin layer chromatography
1949
time resolved spectroscopy and kinetics
1949
nuclear shell model
1950 1950 1951 1951
DNA base complementarity I-strain (internal) protein structures (alpha-helix; beta-sheet; kinks) Verification of absolute configuration of tartaric acid (verification of Fischer's assignments) asymmetric induction conformation in organic synthesis frontier molecular orbital theory intimate and solvent separated ion pairs radio carbon dating Pulse radiolysis NMR lineshape analysis and coalescence phenomena Prebiotic synthesis of amino acids Interpretation of pH rate profiles as straight line segments
1952 1952 1952 1952 1952 1953 1953 1953 1953
19 Rice, F.O./Teller, E. Winstein, S. Engelhardt, V.A. Pauling, L./ Lewis, G.N./Calvin, M. Eyring, H./Laidler, K.J. Eyring, H./Laidler, K.J. Eyring, H./Laidler, K.J. Ingold, C.K. Ingold, C.K./Winstein, S. Pauling, L. Chance, B./Gibson, Q.H. Ingold, C.K. Martin, A.J.P./Synge, R.L.M. Kamen, M. Brown, H.C. Schatz, A./Waksman, S.E. Avery, O.T. Brown, H.C. Purcell, E.M./Bloch, F. Fermi, E. Zavoiskii, E.K. Pauling, L. Ingold, C.K./Hughes, E.D. Meinhard, J.E./Hall, N.F./Keller, C.J./Kirchner, J.K./Miller, J.M. Norrish, R.G.W./Porter, G./Eigen, M. Goeppert-Mayer, M. Chargaff, E. Brown, H.C. Pauling, L./Corey, R.B. Bijvoet, B.M. Cram, D.J. Barton, D.H.R./Hassel, O. Fukui, K. Cram, D.J./Winstein, S. Libby, W.F. Gray, L.H./Boag, J.W. Gutowsky, H.S. Miller, S.L./Urey, H.C. Dixon, M.
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1953 1954 1954 1957 1957 1958 1958 1959
20
1959
Enzyme inhibition plots Dixon, M. special salt effect Winstein, S. Matrix isolation spectrscopy Pimentel, G.C./Porter, G. connection between structure and function of proteins Anfinsen, C.B. electron microscopy Ruska, E./Siegbahn, K. discovery of recombinant DNA Berg, P. electrophoresis Tiselius, A. discovery of metallocenes Wilkinson, G./Fischer, E.O. Temperature jump (T-jump) technique Eigen, M.
1961 1961
chemiosmotic theory octant rule
1962 1962 1962 1962 1962 1962 1962 1962 1963 1964 1964 1964 1964
1964 1965 1966 1967 1967 1968 1968 1969 1969 1969
Mitchell, P. Djerassi, C./ Woodward, R.B. Alpha effect nucleophiles Edwards, J.O./ Pearson, R.G. Photoaffinity labelling Thornton, E.R./ Westheimer, F.H. noble gas compounds (XePtF6) Bartlett, N. non-equilibrium thermodynamics Prigogine, I. RNA codons for protein synthesis Boyer, P. Electron capture detector Lovelock, J.E. Discovery of hydrated electron Boag, J.W. Pulse radiolysis Dorfman, L.M. valence shell electron pair repulsion theory (VSEPR) Gillespie, R.J. QSAR (quantitative structure-activity relationship) Hansch, C. fractionation factor theory Kresge, A.J./Gold, V. retrosynthetic analysis Corey, E,J. density functional theory Parr, R.G./Yang, W./Kohn, W./Becke, A./Lee, C. dye lasers Schaefer, F.P. Discovery of organometallic complexes of dinitrogen Allen, A.D./Senoff, C.V. Delayed excimer fluorescence Birks, J.B. molecular mechanics calculations Allinger, N.L. Enzyme-substrate Pn nomenclature Schechter, I. polarography Heyrovsky, M. scaling laws de Gennes, P.G. laser spectroscopy Bloembergen, N./Schawlow, A.L. principle of microscopic reversibility Ingold, C.K. Pump-probe technique Buettner, A.V./Snavely, B.B./Peterson, O.G.
1970 1970 1971 1971
SNR1 mechanism Factor analysis method discovery of transfer-RNA host-guest chemistry
1972
gauche effect
Bunnett, J.F. Malinowski, E.R. Altman, S./Cech, T.R. Cram, D.J./Lehn, J.M./Pedersen, C.J. Wolfe, S.
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1972
1978 1978 1979 1979
16- and 18-electron rule for organometallic complexes Application of Marcus theory to proton transfer reactions Probe technique to observe invisible transients Captodative effect ligand field theory 3D QSAR analysis
1981 1981 1981
scanning tunnelling microscopy atoms in molecules (AIM) Two laser-two colour experiment
1973
1982 1982 1984 1984
1985 1985 1986 1986 1986 1986 1988 1988
21 Tolman, C.A. Kresge, A.J. Scaiano, J.C. Viehe, H.G. Ballhausen, C.J. Marshall, G.R.
Binnig, G./Rohrer, H. Bader, R.F.W. Bernstein, R.B./ Smalley, R.E./ Rentzepis, P.M./ Scaiano, J.C. proton inventory technique Schowen, R.L. site-directed mutagenesis Smith, M. reactivity-selectivity principle Giese, B. Discovery of organometallic complexes of dihydrogen Kubas, G.J./Ryan, R.R./Swanson, B.I./Vergamini, P.J./Wasserman, H.J. principle of non-perfect synchronization Bernasconi, C.F. discovery of c60 Kroto, H.W./Smalley, R.E./Curl, R.F. general valence bond theory Goddard (III), W.A. atomic force microscopy Binnig, G./Gerber, C./Quate, C.F. Combinatorial chemistry Furka, A. polymerase chain reaction (PCR) method Mullis, K.B. Comparative molecular field analysis (CoMFA) Cramer, R.D. (III) Variable Marcus intrinsic barriers for deprotonation of Bunting, J.W./ carbon acids Stefanidis, D.
1991 1992 1993 1999
Atom economy reaction metric Environmental impact factor reaction metric Laser drop experiment No-barrier multi-dimensional Marcus theory
Trost, B. Sheldon, R.A. Banks, J.T./Scaiano, J.C. Guthrie, J.P.
2002
First observation of distinct steps in SN1 reaction
Mayr, H.
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf
(4) Concepts in Physical Organic Chemistry YEAR 1836 1850 1877 1883 1884 1887 1889 1890 1893 1894 1899 1907 1910 1910 1913 1913 1914 1915 1916 1916 1918 1919 1920 1921 1923 1923 1923 1923 1924 1924 1926 1926 1926 1927 1927 1930 1930 1932 1932
CHRONOLOGY OF CONCEPTS IN PHYSICAL-ORGANIC CHEMISTRY CONCEPT (SCIENTISTS) Berzelius-Ostwald catalysis concept laws of chemical kinetics (van't Hoff, J.H./Wilhelmy, L.F.) tautomerism (Laar, C./Butlerov, A./Baeyer, A./Wislicenus, J./Meyer, K.H./Knorr, L./Nef, J.U./Michael, A.) catalysis (Ostwald, W.) Le Chatelier’s principle ionization theory (Arrhenius, S.) Arrhenius equation chair and boat ring conformations (Sachse, H./Mohr, E.) Walden inversion rule steric effect (Meyer, V.) reaction intermediates concept (carbocations) (Stieglitz, J./Norris, J.F.) Acree-Curtin-Hammett principle directing groups in aromatic chemistry (Holleman, A.F.) Hill plot Bodenstein steady state approximation Michaelis-Menten equation potential energy surfaces (Marcelin, R.) pH indicators (Lubs, H.A./Clark, W.M./Acree, S.F.) covalent bonding (Lewis, G.N.) octet rule (Lewis, G.N./Langmuir, I.) Nernst radical chain Stern-Volmer plot hydrogen bonding (Latimer, W.H./Rodebush, W.H./Huggins, M.L.) electrophilicity-nucleophilicity (Fry, H.S./Bronsted, J.N./Lowry, T.M./Lapworth, A./Lewis, G.N.) Lewis acid inductive effect (Lewis, G.N./Ingold, C.K./Lowry, T.M.) Bronsted catalysis law Bronsted-Lowry acid linear free energy relationships (Bronsted, J.N./Pedersen, K./Hammett, L.P.) mesomeric (resonance) effect (Lucas, H.J./Arndt, F./Ingold, C.K.) Guggenheim method Concept of partial charges in chemical structures (Ingold, C.K./ Ingold, E.H.) Electronic theory of organic chemistry (Robinson, R./Ingold, C.K.) Born-Oppenheimer approximation solvolysis (Ward, A.M./Hammett, L.P.) electrostatic (field) effect (London, F.) Mills-Nixon effect Hammett acidity function Pauling electronegativity scale
22
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1932 1933 1933 1934 1934 1934 1935 1935 1935 1935 1935 1935 1935 1935 1936 1936 1936 1937 1937 1938 1939 1939 1939 1940 1940 1940 1940 1940 1941 1942 1945 1947 1948 1948 1948 1948 1949 1949 1949 1952 1952 1952 1953 1953 1953 1953 1954 1954
Hanes-Woolf plot Bell equation Peroxide effect (Kharasch, M.S./Mayo, F.R.) hyperconjugation (Wheland, G.W.) SN1/SN2 (Ingold, C.K./Hughes, E.D.) Lineweaver-Burk plot Baker-Nathan effect Eyring equation Hammett equation Eyring transition state theory substituent effect (Hammett, L.P.) isotopic exchange (Urey, H.C.) isotopic labelling experiment (Urey, H.C./Ingold, C.K./ Rittenberg, D./Schoenheimer, R.) Müller-Müller-Rodloff biradical rule Gross-Butler equation Bell-Evans-Polanyi principle isotope effect (Reitz, O.) crossover experiment (Hurd, C.D.) acidity function (Hammett, L.P.) principle of least motion (Rice, F.O./Teller, E.) Zucker-Hammett hypothesis anchimeric assistance (Winstein, S.) Electrode kinetics (Eyring, H./Laidler, K.J.) common ion effect (Ingold, C.K.) normal salt effect (Ingold, C.K./Winstein, S.) Stopped-flow technique (Chance, B./Gibson, Q.H.) Heterogeneous catalysis (Eyring, H./Laidler, K.J.) Solvent effects in kinetics (Eyring, H./Laidler, K.J.) A1 and A2 mechanisms (Ingold, C.K.) Wheland intermediate Pitzer ring strain Bigeleisen-Wolfsberg equation Grunwald-Winstein equation hybridization in chemical bonding (Pauling, L.) E1/E2 eliminations (Ingold, C.K./Hughes, E.D.) "push-pull" mechanism (Swain, C.G.) time resolved spectroscopy and kinetics (Norrish, R.G.W./Porter,G./ Eigen, M.) Scatchard plot Kinetics of urea-urease enzyme system (Laidler, K.J.) Taft equation conformation in organic synthesis (Barton, D.H.R./Hassel, O.) intimate and solvent separated ion pairs (Cram, D.J./Winstein, S.) Doering-Zeiss intermediate Leffler hypothesis Swain-Scott equation NMR lineshape analysis and coalescence phenomena (Gutowsky, H.S.) Curtin-Hammett principle special salt effect (Winstein, S.)
23
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1954 1955 1955 1956 1956 1956 1957 1958 1958 1959 1959 1961 1962 1962 1963 1963 1963 1963 1964 1964 1964 1965 1966 1967 1968 1968 1969 1969 1969 1970 1970 1970 1971 1972 1972 1972 1975 1975 1976 1976 1977 1977 1977 1977 1978 1978 1981 1981
Matrix isolation spectroscopy (Pimentel, G.C./Porter, G.) Hammond postulate Winstein-Holness equation Edwards equation Marcus equation King-Altman method Gillespie-Nyholm model Swain-Schaad equation Kosower Z-values Corey-Pauling-Koltun space filling models Temperature jump (T-jump) technique (Eigen, M.) Westheimer principle Discovery of hydrated electron (Hart, E.J./Boag, J.W.) Pulse radiolysis technique (Dorfman, L.M.) Pearson's HSAB principle Cleland rules Muetterties rule valence shell electron pair repulsion theory (VSEPR) (Gillespie, R.J.) Eigen curve fractionation factor theory (Kresge, A.J./Gold, V.) density functional theory (Parr, R.G./Yang, W./Kohn, W./Becke, A./Lee, C.) Woodward-Hoffmann rules Bunnett-Olsen equations molecular mechanics calculations (Allinger, N.L.) Swain-Lupton equation magic or super acid (Gillespie, R.J./Olah, G.A.) Edward-Lemieux effect (anomeric effect) Hansch constant principle of microscopic reversibility (Ingold, C.K.) More O'Ferrall-Jencks diagram SNR1 mechanism (Bunnett, J.F.) Factor analysis method (Malinowski, E.R.) host-guest chemistry (Cram, D.J./Lehn, J.M./Pedersen, C.J.) Ritchie equation Koppel-Palm solvent parameters gauche effect (Wolfe, S.) Three phase test for reaction intermediates (Rebek, J.) Bordwell carbon acidity scale in polar non-hydrogen-bond solvents Kamlet-Taft solvent parameters Baldwin's rules Kaptein-Closs rules Jencks' clock Concept of philicity of singlet carbenes (Moss, R.A.) Probe technique to observe spectroscopically “invisible” transients (Scaiano, J.C.) Cox-Yates acidity function Captodative effect (Viehe, H.G.) atoms in molecules (AIM) (Bader, R.F.W.) Keeffe-Jencks equations
24
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1982 1984 1985 1986 1988 1988
25
proton inventory technique (Schowen, R.L.) reactivity-selectivity principle (Giese, B.) principle of non-perfect synchronization (Bernasconi, C.F.) general valence bond theory (Goddard (III), W.A.) Boyd-Edgecombe electronegativity parameters Variable Marcus intrinsic barrier for deprotonation of carbon acids (Bunting, J.W./Stefanidis, D.) Lever ligand electrochemical parameters No-barrier multi-dimensional Marcus theory (Guthrie, J.P.) First observation of distinct steps in SN1 reaction (Mayr, H.)
1990 1999 2002
Bolded entries correspond to those with Canadian connections. GROWTH OF IDEAS AND CONCEPTS IN PHYSICAL-ORGANIC CHEMISTRY
NUMBER OF IDEAS AND CONCEPTS
35
30
25
20
15
10
5
DECADE
(5) Laboratory Apparatus
Nationality German British French American
Number of Chemists 22 9 5 5
2001 - 2010
1991 - 2000
1981 - 1990
1971 - 1980
1961 - 1970
1951 - 1960
1941 - 1950
1931 - 1940
1921 - 1930
1911 - 1920
1901 - 1910
1891 - 1900
1881 - 1890
1871 - 1880
1861 - 1870
1851 - 1860
1841 - 1850
1831 - 1840
0
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf Italian Swiss Swedish Canadian Polish Danish Dutch
Year 1724 1742 1823 1836 1844 1874 1876 1879 1879 1886 1888 1888 1888 1888 1895 1900 1901 1905 1907 1908 1908 1910 1910 1911 1912 1913 1914 1917 1919 1919 1920 1924 1924 1925 1932 1932 1936 1936 1937 1944
2 2 1 1 1 1 1 51 Laboratory Apparatus Fahrenheit temperature scale Celsius temperature scale Dobereiner lamp Daniell cell Kipp gas generator McLeod vacuum gauge Viktor Meyer tube Gooch crucible Soxhlet extractor Allihn condenser Kjeldahl flask Beckmann thermometer Hirsch funnel Büchner funnel Pulfrich refractometer Parr calorimeter bomb Schott glass Dewar flask Davies double surface condenser Geiger counter Vigreux column Knudsen vacuum gauge Abderhalden drying pistol Ketene lamp Friedrichs condenser Schlenk flask Raschig rings Thiele tube Dufton column Friedrichs filter funnel Dean-Stark apparatus Widmer column Parnas apparatus Pulfrich photometer Fenske rings Gaede oil diffusion pump Hershberg stirrer Stedman column Penning vacuum gauge Pirani vacuum gauge
26
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1948 1956 1963
Holzman column Beckman pH meter Lessing rings Bunsen burner Claisen adapter Claisen flask Dimroth condenser Dixon gauze rings Erlenmeyer flask Griffin beaker Hempel column Hempel pipet Liebig condenser Mariotte bottle Pasteur pipet Perkin triangle Vernier calipers West condenser Zimmerli vacuum gauge
(6) Named Organic Reactions Nationality German American American-born British Russian French Swiss Japanese Italian Canadian Belgian Czech Austrian Australian Ukrainian Swedish Hungarian Polish Dutch Romanian TOTAL
Number of Chemists 114 63 48 30 19 16 11 8 5 4 5 4 4 2 2 2 2 2 2 1 342
27
Decade 1998 - 2007
1988 - 1997
1978 - 1987
30
1968 - 1977
1958 - 1967
1948 - 1957
1938 - 1947
1928 - 1937
1918 - 1927
1908 - 1917
1898 - 1907
1888 - 1897
1878 - 1887
1868 - 1877
1858 - 1867
1848 - 1857
1838 - 1847
1828 - 1837
Number of Reactions Discovered
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 28
Organic Name Reactions Timeline Number of Reactions Not Named After People
Number of Reactions Named After People
25
20
15
10
5
0
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf
29
CUMULATIVE GROWTH OF ORGANIC REACTIONS DISCOVERED SINCE WOHLER'S UREA SYNTHESIS OF 1828
CUMULATIVE NUMBER OF ORGANIC REACTIONS DISCOVERED
300
250
200
150
100
50
YEARS
Year
Named Reactions
1828 1836 1838 1849 1850 1852 1853 1855 1856 1858 1860 1862 1863 1864 1868 1869 1870 1871
Wohler urea synthesis Marsh arsenic test Aldol condensation (Kane, R.); Benzilic acid rearrangement (Liebig, J.) Fehling Strecker amino acid synthesis Williamson ether synthesis Cannizzaro Wurtz Aromatic nitration (Kopp, H.) Griess diazotization Kolbe-Schmitt; pinacol rearrangement (Fittig, R.) Aromatic halogenation (Muller, H./Schramm, J./Seelig, E./Scheufelen, A.) Benzidine rearrangement (Hofmann, A.W.) Wurtz-Fittig, Schiff base Perkin reaction Glaser coupling Perkin rearrangement Hofmann-Martius rearrangement, von Richter, aromatic sulphonation (Meyer, V.) Lossen rearrangement, Beilstein Reimer-Tiemann Friedel-Crafts acylation and alkylation
1872 1876 1877
2002
1985
1978
1973
1968
1963
1957
1952
1946
1940
1934
1928
1923
1918
1911
1906
1901
1895
1889
1884
1877
1869
1860
1852
1828
0
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1880 1881 1882 1883 1884 1885 1886 1887 1888 1889 1890 1891 1893 1894 1895 1897 1898 1899 1900 1901 1902 1903 1904 1905 1906 1907 1908
1909 1910 1911 1912 1913 1914 1915 1918 1919 1920 1921
Skraup, Wallach Claisen-Schmidt, Hell-Volhard-Zelinsky, Hofmann elimination, Etard, Ciamician pyridine synthesis from pyrrole Friedlander, Hantzsch pyridine synthesis, Tollens test, Radziszewski Doebner-Miller, Fischer indole synthesis, Hofmann-Loffler-Freytag, von Pechmann Schotten-Baumann, Sandmeyer, Elbs Kiliani-Fischer, Paal-Knorr, Leuckart Beckmann rearrangement, Knorr, Fischer-Hepp rearrangement, Jaffe's reaction, Janovsky reaction Claisen condensation, Gabriel, Michael addition, Reformatskii Japp-Klingemann Liebermann-Burchard method or reaction Curtius, Gatterman, Menshutkin, Hinsberg test Tiemann rearrangement Bischler-Napieralski, Fenton, Ruff-Fenton degradation, Stobbe condensation, Wohl degradation, Biginelli Bamberger rearrangement, Frisch-Buttenberg-Wiechell, Dieckmann, Nef Delepine, Fischer esterification, Henry, oxidation of olefins with permanganate (Wagner, G.), Lobry de Bruyn-van Eckenstein transformation Gatterman-Koch Arbuzov-Michaelis, Knoevenagel condensation Baeyer-Villager oxidation, Chugaev, Wagner-Meerwein rearrangement Grignard Ciamician photodisproportionation Orton rearrangement Bouveault-Blanc, Tiffeneau-Demjanov rearrangement; Benzoin condensation (Lapworth, A.J.), Lapworth Bucherer, Darzens, Thorpe, Ullmann Eschweiler-Clarke, Harries ozonolysis; Acyloin condensation (Bouveault, L.) Tischenko; Zincke reaction; Chichibabin pyridine condensation Malonic ester synthesis (Perkin, W.H. Jr.), hemiacetals/hemiketals formation (Jackson, C.L.) Fries rearrangement, esterification with diazomethane (Herzig, J./Wegschneidler, R./Bouveault, L.), acyl rearrangement (Auwers, K. von/Fischer, Emil) Paterno-Buchi, Willgerodt, Prilezhaev, Benedict test Pummerer rearrangement, Finkelstein; Acetoacetic ester synthesis (Simonsen, J.L.) Wolff-Kishner reduction; Pictet-Spengler isoquinoline synthesis, Abderhalden ninhydrin Barbier-Wieland, Claisen rearrangement, Maillard, Mannich, Wolff rearrangement; Allylic rearrangement (Claisen, L.) Clemmensen reduction, Favorskii rearrangement Chichibabin pyridine amination Houben-Hoesch Rosenmund reduction, Weerman degradation Meisenheimer, Staudinger, Prins Vinyl ether rearrangement (Adams, R.) Dienone-phenol rearrangement (von Auwers, K.), Passerini
30
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1922 1923 1924 1925 1926 1927 1928 1929 1930 1931 1932 1933 1934 1935
1936 1937 1939 1940 1941 1942 1944 1945 1946 1948 1949 1950 1951 1952 1953 1954 1955 1956 1957 1958 1959 1960 1961 1963 1964 1965
Meyer-Schuster rearrangement Fischer-Tropsch process, Nametkin rearrangement Bachmann-Gomberg; Zemplen's saponification, acetals/ketals formation (Skrabal, A.) Chapman rearrangement, Meerwein-Pondorff-Verley, Stephen reduction Neber, Rupe rearrangement, Zemplen degradation of sugars Vilsmeier-Haack-Arnold, Schiemann, Polonovski Diels-Alder, Stevens rearrangement, Dakin-West reaction Neuberg degradation, Nenitzescu indole synthesis, Nesmeyanov's diazo method Lucas test, Schoenberg rearrangement, Schoenberg reaction Criegee, haloform reaction (Fuson, R.C.) Haworth phenanthrene synthesis; Bergmann-Zervas Cbz method Helferich method; Prevost reaction; epoxide rearrangement (Paul, R./Tiffeneau, M.) Nieuwland enyne synthesis Arndt-Eistert synthesis, Robinson annulation, Smiles rearrangement, Wenker synthesis, Lohmann transphorphorylation; cyclopropanation with diazomethane (Fischer, Hans), hydrogenolysis of benzyl ethers (Adkins, H.) Hooker oxidation, McFadyen-Stevens rearrangement, Norrish Type I/II, Nenitzescu reductive acylation Hammick, Sommelet-Hauser, Oppenauer oxidation Meerwein arylation, Marschalk Ramberg-Backland, Cope rearrangement Dakin Borodin-Hunsdiecker, Wittig rearrangement Birch reduction, Bartlett-Condon-Schneider, Criegee rearrangement Kharasch cyclization, Sanger reaction Jones oxidation, Nazarov cyclization Ritter, LAH reduction of methyl esters (Karrer, P./Bachmann, W.E.) Cope elimination, Cornforth rearrangement, LAH reduction of ketones Edman degradation, Wessely oxidation, oxymercuration of olefins (Brook, A.G./Wright, G.F.) Borohydride reduction (Wolfrom, M.L./Woodward, R.B.) Bamford-Stevens, Benkeser reduction, Macdonald coupling Sarett procedure Eglinton, Stork enamine synthesis, Wittig reaction Grob fragmentation, Fischer-Hafner reaction Lemieux-Johnson oxidation; Hydroboration (Brown, H.C.) Cadiot-Chodkeivicz, aniline synthesis via arynes (Bunnett, J.F./Roberts, J.D.) Brook rearrangement, Horner-Emmons, Simmons-Smith cyclopropanation, Asinger McLafferty rearrangement, Wacker, Nenitzescu synthesis of pyrylium salts Barton, Martynoff rearrangement, Wawzonek-Yeakey rearrangement, pyrolysis of sulfoxides (DePuy, C.H./Cram, D.J.) Wharton, Wadsworth-Emmons, diimide reduction (Corey, E.J./van Tamelen, E.E.), 1,3-dipolar additions (Huisgen, R.) Corey-Winter, Merrifield solid phase synthesis, Pfitzner-Moffatt oxidation tosylhydrazone reduction (Caglioti, L.) Graham, Kochi
31
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1966
1979 1980 1983 1982 1985 1988 1989 1990
sulfenate-sulfoxide rearrangement (Mislow, K.), Newman-Kwart rearrangement Kemp, Shapiro, Regitz diazo group transfer, Eschenmoser fragmentation Peterson oxidation, Weiss Di-pi-methane rearrangement (Zimmerman), Meyers aldehyde synthesis, Schlosser modification of Wittig Mitsunobu, dehalogenation with nBu3SnH Nicholas reaction Corey-Kim, Heck, Borch reduction, Bergman cyclization, Claisen-Ireland, TMS enolate rearrangement (Ireland, R.E.), Kinugasa Julia synthesis, Pauson-Khand McMurry, Mukaiyama aldol, Danishefsky, vinylogous Wolff rearrangement (Smith, A.B. III) Ugi condensation, Dotz, Barton-McCombie, Sharpless oxyamination Stetter Hosomi-Sukarai, Negishi coupling Stille coupling, Swern oxidation, Murahashi, Still-Wittig, Tebbe olefination, Vorbrueggen coupling Suzuki coupling Sharpless epoxidation Dess-Martin oxidation, Nozaki Mukaiyama-Michael Noyori Grieco condensation Sharpless-Jacobsen hydroxylation, Kulinkovich Jacobsen epoxidation
1997 1998
Petasis condensation Uemura oxidation
2002 2002 2003
Stahl oxidative amination Liebeskind-Srogl coupling Jacobs oxidative coupling, Stoltz oxidative etherification
1967 1968 1969 1970 1971 1972 1973 1974 1975 1976 1977 1978
Timeline of Discovery of Organic Reactions
Decade
1828 - 1837 1838 - 1847 1848 - 1857 1858 - 1867 1868 - 1877 1878 - 1887 1888 - 1897
Number of Reactions Named After People 1 1 5 4 10 29 21
Number of Reactions Not Named After People 0 2 1 3 1 0 2
32
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1898 - 1907 1908 - 1917 1918 - 1927 1928 - 1937 1938 - 1947 1948 - 1957 1958 - 1967 1968 - 1977 1978 - 1987 1988 - 1997 1998 - 2007 TOTAL
20 19 19 28 14 16 22 22 12 5 5 253
4 4 3 4 0 6 5 4 0 0 0 39
(7) Named Reagents, Catalysts, and Compounds YEAR 1658 1672 1789 1822 1825 1827 1827 1844 1845 1849 1850 1851 1851 1851 1855 1856 1857 1863 1864 1867 1867 1869 1875 1876 1876 1876 1878 1879 1879 1879 1880 1880 1880
REAGENT/CATALYST DISCOVERED Glauber's salt Rochelle/Seignette salt Eau-de-Javelle Gmelin's salt Eau de Labarraque Zeise's dimer Zeise's salt Peyrone's salt Fremy's salt Fehling solution Laurent's acid Piria's acid Sobrerol Sobrerone Mohr's salt Nessler reagent Schweizer's reagent Reinecke salt Schiff's base Martius yellow Dewar benzene Ladenburg benzene Cleve's alpha acid Lauth's violet Ebert and Merz acids Michler's ketone Cleve's delta acid Meldola's blue Michler's hydride/base Würster's dyes (blue and red) Wallach intermediate Nevile and Winther's acid Ringer's solution
33
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1882 1882 1883 1886 1886 1887 1887 1887 1888 1891 1893 1893 1893 1894 1895 1896 1896 1897 1898 1899 1900 1900 1900 1900 1901 1904 1904 1904 1905 1906 1907 1907 1907 1908 1909 1910 1910 1913 1914 1915 1916 1917 1919 1921 1922 1923 1924 1924 1925 1925
Tollens reagent Broenner's acid Bindschedler's green Cleve's gamma acid Janovsky's complex Reformatskii reagent Troeger's base Cleve's beta acid Forsling's acid Armstong and Wynne's acid Fenton reagent Tobias acid Hagemann's ester Jaffe's base Freund's acid Piloty's acid Angeli's salt Wurster's reagent Caro's acid Muthmann's liquid Meisenheimer complex Thiele reagent Gomberg radical Grignard reagent Kiliani reagent Kunig's salt Schardinger sugars Thiele's hydrocarbon (biradical) Staudinger's ketene Harden and Young's ester Willstatter imines Pope's complex Chichibabin hydrocarbon (biradical) Meldrum's acid Benedict's solution Ruhemann's purple Niementowski's dye Meerwein ester Evans blue Schlenk-Brauns biradical Lewis structures Mannich's bases Claisen's alkali Rosenmund catalyst Adam's catalyst Broensted catalyst Fieser's solution Markush structures Lewisite Neuberg ester
34
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1926 1927 1927 1927 1933 1934 1935 1935 1936 1937 1937 1937 1938 1939 1941 1941 1942 1942 1943 1943 1943 1945 1946 1947 1950 1950 1950 1951 1952 1953 1953 1954 1955 1955 1957 1957 1958 1958 1958 1959 1959 1960 1960 1960 1961 1961 1961 1961 1962 1962
Banfield-Kenyon radical Raney nickel Vilsmeier reagent Gibbs reagent Raybin’s reagent Schoenberg's reagent Karl Fischer reagent Kohler's ketone Gilman reagents Meerwein salt Reichstein substance G Cori ester Sheibley's reagent Bratton-Marshall reagent proton sponge Müller's hydrocarbon (biradical) Wheland intermediate Tsuda reagent Lazier catalyst Girard reagent P Girard reagent T Sanger's reagent Jones reagent Heyns catalyst Wieland-Miescher ketone Adkins catalyst Edman's reagent ferrocene Lindlar's catalyst Nazarov's reagent Sarett reagent Wittig reagent Zeigler-Natta catalyst Lemieux-von Rudloff reagent Koelsch radical Coppinger's radical Simmons-Smith reagent Hunig's base Lemieux-Johnson reagent Ellman's reagent Nenitzescu's dimer Nishimura catalyst Gold's reagent Tuppy's maleimide Payne's reagent Snatzke's reagent Woodward's reagent Sawicki’s reagent Cornforth reagent Vaska compound
35
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1963 1963 1964 1964 1964 1965 1965 1965 1967 1967 1967 1967 1968 1968 1968 1968 1968 1968 1968 1969 1969 1969 1969 1971 1971 1971 1971 1971 1972 1972 1972 1972 1973 1973 1973 1973 1974 1974 1975 1975 1975 1975 1977 1978 1978 1978 1979 1979 1981 1981
Pfitzner-Moffatt reagent Merrifield resin Fischer carbene Nenitzescu's dichloride Koshland reagent number 1, 3 Wilkinson's catalyst Koshland reagent number 2 Petitt complex Mosher's acid Mosher esters Mosher amides Mosher's acid chloride Lawesson's reagent Bredereck's reagent Burgess reagent Collin's reagent Fetizon's reagent Karstedt catalyst Cleland reagent Mitsunobu reagent Creutz-Taube complex Magic acid (Olah, G.A.) Walborsky reagent Seyferth-Gilbert reagent Viehe's salt Eschenmoser's salt Martin sulfurane dehydrating agent Rondeau's reagent Collman's reagent Corey-Kim reagent Lalancette's reagent Nenitzescu's hydrocarbon Olah's reagent Pearlman's catalyst Eaton reagent Wang resin McMurry's reagent Schwartz's reagent Moore's ketene Mukaiyama's reagent Bates reagent Nysted reagent Crabtree's catalyst Swern reagent Tebbe reagent Meyers reagent Midland's reagent Noyori reagent Kemp's triacid Evans auxiliary
36
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 1981 1982 1982 1983 1983 1983 1984 1985 1986 1986 1986 1987 1989 1990 1991 1992 1999
Weinreb amide Koser's reagent Davy reagent methyl Reichardt's dye Barton ester Belleau reagent Marfey’s reagent Appel's reagent Vedejs reagent Williams glycinate Van Boom’s reagent Hendrickson's reagent Brown's reagent Oppolzer's auxiliary Jacobsen's catalyst Petasis reagent Grubbs ruthenium catalyst Adam's reagent Adamite Adamsite Aldrin Andresen's acid Badische acid Bayer's acids Corey aldehyde Corey lactone Corey's reagent Dahl's acid I Dahl's acid II Dahl's acid III Dieldrin Ehrlich's reagent Fieser's reagent Kalle's salt Koch's acid Marignac's salt Reichstein's substance S Schaeffer's acids Schollkopf's acid
37
DECADE 2007 - 2016
1997 - 2006
1987 - 1996
1977 - 1986
1967 - 1976
1957 - 1966
1947 - 1956
1937 - 1946
1927 - 1936
1917 - 1926
1907 - 1916
1897 - 1906
1887 - 1896
1877 - 1886
1867 - 1876
1857 - 1866
1847 - 1856
1837 - 1846
1827 - 1836
NUMBER OF NAMED COMPOUNDS DISCOVERED
Dr. John Andraos, http://www.careerchem.com/NAMED/Statistics-A.pdf 38
DISCOVERY OF REAGENTS, CATALYSTS, AND NAMED COMPOUNDS TIMELINE
35
30
25
20
15
10
5
0
