ORGANIC CHEMISTRY AND BIOCHEMISTRY

in the 19th and 20th Centuries

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To view parallel developments in either of the following areas, click on "GEN" or "ELT/TECH" in any decade.

Contemporary General, Analytical and Physical Chemistry = "GEN"
Elements and Contemporary Events and Technology = "ELT/TECH"


ORGANIC CHEMISTRY

DECADE

BIOCHEMISTRY

BERZELIUS' DUALISTIC THEORY: All compounds, organic or inorganic, consist of a positive and a negative part. Elements are either electropositive or electronegative.
By 1834, with FARADAY's Electrochemical work, Dualism is dealt a severe blow.

GAY-LUSSAC and THENARD on iodine and cyanogen. (First compound "radical"; later leads to Radical Theory)

1816: Naphthalene from coal tar
First isolated:
  • Strychnine
  • Brucine
  • Quinine
  • Morphine

1810

 GEN
ELT/TECH

Return to top. 		Beginnings of Biochemistry
1815: Sugar from starch and cellulose----
G. S. KIRCHHOFF

BIOT notes optical activity of sugars, etc.

1818: CHEVREUL discovers cholesterol.

Maltose first isolated.
"We may concede at the outset that in 1825 it would have been utterly impracticable to determine the constitution of an organic compound in the sense in which we use the expression." ---Moore
1823: Isomerism of cyanates and fulminates---
LIEBIG and WÖHLER.

1825: FARADAY: Discovery of benzene and hydrocarbon isomerism.

1826: Discovery of aniline.

1828: WÖHLER: Urea from ammonium cyanate; part of impetus for Era of Synthetic Organic Chemistry (see below).
By his synthesis of an "organic" substance (urea) from an "inorganic" substance (ammonium cyanate), Wöhler disproves the theory long held by BERZELIUS and others that a "vital force" animates organic substances. Based on this development,

THE ERA OF SYNTHETIC ORGANIC CHEMISTRY BEGINS.

1828: DUMAS' Etherin Theory: Organic compounds
are addition products of ethylene.

Radical Theory.

1820

 GEN
ELT/TECH

Return to top. 		1823: CHEVREUL'S "RECHERCHES CHIMIQUES
  SUR LES CORPS GRAS D'ORIGINE ANIMALE."
Foundation of the chemistry of fats.
Nicotine isolated.
1830: Amygdalin isolated.
Isomerism of tartaric and racemic acids.
---BERZELIUS

DUMAS: Determination of organic nitrogen
by combustion method.
1831: Atropine isolated.
1831: LIEBIG: Perfection of combustion methods for organic carbon and hydrogen analyses.
THE RADICAL THEORY: radicals are capable of separate existence. Suggested, elaborated or supported by:
  • ~1812: GAY-LUSSAC and THENARD on iodine and cyanogen. (First compound "radical." )
  • (1828) DUMAS' Etherin Theory (Organic comounds are addition products of ethylene).
  • (~1830) BERZELIUS who writes: "An oxide cannot be a radical." Suggests other groups.
  • 1832: LIEBIG and WÖHLER: on the Benzoyl Radical.
  • (~1835) LIEBIG and DUMAS: "Organic chemistry is the chemistry of radicals."
  • 1839: BUNSEN on Cacodyl.
    LIEBIG'S Acetyl Theory.
Vicinity of "Radical Theory"
in Mallinckrodt Poster

1834: Pyrrol from bone-oil.
Observation: platinum hastens the combustion of hydrogen. Leads to studies of catalysis by BERZELIUS and his description of enzyme action.

(~1835) LAURENT: The Nucleus Theory.

Observation of substitution of chlorine for hydrogen in wax, etc., leads to DUMAS' synthesis of trichloroacetic acid from acetic acid; thus the downfall of both Dualism and the Radical Theory and the postulation of the Nucleus Theory (~1835) by LAURENT and "Copulated" (sic) compounds by BERZELIUS (~1840).

1837: LIEBIG and WÖHLER on uric acid.
1839: DUMAS: Trichloroacetic acid from acetic acid.

The first TYPE THEORY

Vicinity of "Type Theory"
in Mallinckrodt Poster
(scroll down the Poster
past the "Radical Theory")

1830



GEN
ELT/TECH Return to top. 		1833: BEAUMONT'S "EXPERIMENTS AND OBSERVATIONS ON THE GASTRIC JUICE, AND THE PHYSIOLOGY OF DIGESTION."

Diastase from barley and malt--- PAYEN and PERSOZ.

MAGENDIE differentiates foodstuffs into proteins, carbohydrates and fats.

1836: SCHWANN describes pepsin. BERZELIUS earlier described enzyme action.
BERZELIUS: Copulated compounds. (~1840)
( SECOND TYPE THEORY)

1842: Quinoline--- GERHARDT

HOFMANN'S work on aniline and coal tar: aniline and benzene in coal tar.
first aniline dye (mauve, 1856)

Nitration of benzene
The first TYPE THEORY: Substances of the same "type" contain the same number of equivalents united in the same manner and have similar chemical properties. This theory broke the connection between organic and inorganic compounds.
SECOND TYPE THEORY (approximately 1850)
Vicinity of "Type Theory"
in Mallinckrodt Poster
(Scroll down the Poster
below the "Radical Theory.")

1846: Pyridine bases from bone-oil
--- T. ANDERSON.
1848: Isomerism of lactic acid.

WURTZ discovers amines and their relation to ammonia; leads to SECOND TYPE THEORY

1840



GEN
ELT/TECH Return to top. 		First theory of protein metabolism. Protein the essential foodstuff; fat and carbohydrate only thermogenic and respiratory. Urinary nitrogen a measure of protein breakdown.
1842: LIEBIG: "DIE THIERCHEMIE." Example of Liebig's powerful influence on physiology.

Ether anesthesia--- MORTON.
Pancreatic amylase.

1847: LIEBIG: Composition of meat juice.
Fructose isolated.
1850: WILHELMY: Inversion of sugar by acids.
First reaction rate equation.

PASTEUR on tartaric acid. Asymmetric molecules and optical activity. ( earliest (1874) ideas of STEREOCHEMISTRY)

1850-1852: WILLIAMSON discovers the true constitution of ethers and shows them to be of the Water Type (supporting the formulation of the SECOND TYPE THEORY).
THE SECOND TYPE THEORY: Organic and inorganic compounds are related; there can be compounds which exemplify "Multiple Types" and "Mixed Types." The second TYPE THEORY was also supported by the work of LAURENT and GERHARDT.
Vicinity of "Type Theory"
in Mallinckrodt Poster
(Scroll downward on the Poster,
below "Radical Theory")


KOLBE and FRANKLAND revive
THE RADICAL THEORY
(Radicals exist as such in compounds.
Supports reality of types.)

WURTZ synthesis.

KOPP: relationship between boiling point and chain length, molar mass.

PERKIN (1856): First aniline dye (mauve).
GERHARDT (~1855): Formulas can only express reactions and relations of compounds. Atomic arrangements are impossible to determine.
1858: KEKULÉ: Quadrivalence of carbon and formation of carbon chains.
GRIESS (1858): Study of diazo compounds.

1850



GEN
ELT/TECH Return to top. 		REGNAULT and REISET on the Respiratory Quotient.

BERTHELOT (1854): Study of glycerol and synthesis of fats.

(1855): First observation of mutarotation (lactose).

CORVISART (1856): describes trypsin.

PASTEUR on fermentation. Question of abiogenesis answered.

BERNARD (1857) discovers glycogen in liver.

VOIGT (1859): conception of nitrogenous equilibrium.
HOFMANN (1860) on fuchsine
LAUTH (1861): Methyl violet.
LIGHTFOOT (1863): Aniline black.
1864: First azo dye (aniline yellow) commercialized.
GRAEBE and LIEBERMANN'S synthesis of alizarin.
( Baeyer's synthesis of indigo )
(~1880)
BERTHELOT and DE ST. GILLES (1860):
Hydrolysis of esters and velocity of reaction.
( Law of Mass Action )

1863: Acetoacetic ester--- GUETHER

FITTIG synthesis.

Graphic formulas--KEKULÉ, COUPER

MODERN CONCEPTION OF VALENCE
AND MOLECULAR STRUCTURE

1860



GEN
ELT/TECH Return to top. 		TRAUBE: Oxidation takes place in cells, not blood or lungs.

THUDICUM'S work (~1866) on cerebrosides, etc.

VOIGT: Theory of protein metabolism.
Circulating and tissue protein.

MIESCHER: Nuclein from pus cells.
( preparation of protamine)
MARKOVNIKOV'S rule. (1870)

KÖRNER: isomerism of aromatic compounds. (1874)

VAN'T HOFF and LE BEL independently establish (1874) the foundations of STEREOCHEMISTRY. (built on work of PASTEUR(~1850)).
Asymmetric carbon atom (~1895)

E. FISCHER studies of the hydrazines
later (~1882) work on composition of the sugars.
(Osazones)

FRIEDEL-CRAFTS synthesis.

WITT: Chromophore-auxochrome theory of color.

( synthesis of alizarin(1867) )
BAEYER'S Synthesis of indigo.

THE COAL TAR INDUSTRY

which built upon technological developments by Knab and Carves (coke oven).

(coal + heat coke + coal "tar")

coal "tar" various precursors to dyestuffs) and Semet and Solvay (oven).

1879: Polymerization of isoprene into "rubber."

1870



GEN
ELT/TECH Return to top. 		BERTHELOT: "It is the object of these researches to do away with life as an explanation wherever organic chemistry is concerned."

PFLÜGER (1872): Oxidation occurs in tissue, not blood.
(1875) First acid hydrolysis of protein.

MIESCHER prepares protamine.

KOSSEL (1879) begins work on nucleins.

RUBNER: Isodynamicity of foodstuffs.
VICTOR MEYER: Thiophene. Stereoisomerism of nitrogen compounds. (1883)

KJELDAHL method (1883) for nitrogen determination.

LAAR: "Tautomerism" (1885)
BAEYER'S Strain Theory. (~1886)

CLAISEN: acetoacetic ester synthesis (1887).

BAEYER on the constitution of benzene. (~1888)

1880



GEN
ELT/TECH Return to top. 		E. FISCHER on composition of the sugars. (Osazones) Basis of carbohydrate chemistry.

"HOFMEISTER Series": Effect of ions on the swelling of proteins, etc. (1888)
NEF: bivalent carbon (1892).
(note later trivalent carbon)

E. FISCHER on composition of uric acid derivatives.

The "WALDEN" inversion.

VAN'T HOFF and LE BEL:
the asymmetric carbon atom.

SABATIER on hydrogenation.

EHRLICH: Organometallic compounds for
chemotherapy. (1898)

1899: THIELE'S partial valence theory.

1890



GEN
ELT/TECH Return to top. 		E. FISCHER: Investigations of enzyme specificity (1894).

The CRUM BROWN substitution rule.

E. FISCHER on the composition of uric acid derivatives.
E. FISCHER on composition of the proteins.

Mutarotation of glucose.
BUCHNER: Extracellular enzymes.

EIJKMAN on beri-beri (1897): "Deficiency disease" recognized.
BERTRAND: Recognition of co-enzymes.

ABEL and CRAWFORD: Isolation of adrenalin.
C. Hill: First enzymatic synthesis, isomaltose. (1896)

ATWATER-BENEDICT calorimeter.
EHRLICH: Organometallic compounds for chemotherapy. (1898)
1900: Trivalent carbon---GOMBERG
(note earlier bivalent carbon)

1900: GRIGNARD: Developed organomagnesium halide as intermediate for preparing other organics and organometallics.

1904: KIPPING: investigation of silanes (the basis for later development of silicone chemistry)

VICTOR MEYER'S esterification law
---Steric hindrance.

1906: TSWETT: Introduction of chromatography.

WALLACH on terpenes, etc.

1900



GEN
ELT/TECH Return to top. 		1902: BAYLISS and STARLING:
Discovery of first "hormone"--- secretin.

KOSSEL'S isolation of protamine. Theory of protein composition.

1904: CHITTENDEN: Nitrogen balance.

1905: KNOOP: β oxidation theory

1905: STARLING: Introduced the word "hormone."
WILLSTÄTTER'S synthesis of atropine.

SYNTHETIC DRUGS

1906: Beginning of WILLSTÄTTER'S work on chlorophyll. ( Later work)

1906: TSWETT: Introduction of chromatography.

1907: HOPKINS: Amino acids in nutrition.

Use of "pH"---- SØRENSEN
Enzyme activity and pH.
1910: PREGL: MICROANALYSIS.


POLYMERS (chemistry and synthesis)
STAUDINGER.

1910



GEN
ELT/TECH Return to top. 		1911: FUNK on the constitution of "vitamines". Recall (1897) and "deficiency disease."
1911: DONNAN Law of Membrane Equilibrium.

LEVENE, JONES, et al., on nucleic acids.

1913: WILLSTÄTTER and STOLL:
"UNTERSUCHUNGEN ÜBER
CHLOROPHYLL" ("Research about Chlorophyll").

1914: OSBORNE and MENDEL: Amino acids and growth ( and man: ROSE )

1916: FREUNDLICH and LANGMUIR: Adsorption isotherm. HILL, MEYERHOF, EMBDEN, et al. on lactic acid and muscular action.

WIELAND and WINDAUS: Steroid structures.

1919: KENDALL: Thyroxin.
HOPKINS: Glutathione

MACLEOD, BANTING, and BEST: Insulin.
( HORMONES )
1920: KRATZER --- Molecular spectra.
Infrared spectroscopy ( STRUCTURE)

POLYMERS, their chemistry and synthesis.
CAROTHERS
(condensation polymers)
STAUDINGER:
Macromolecular Hypothesis.

MARK: Crystallographic Structure
(of polymers).
KUHN (1930 application of
statistics to polymers).

1926: ANTIMALARIALS: PAMAQUIN

FLEMING: Penicillin ANTIBIOTICS
Structure

1920



GEN
ELT/TECH Return to top. 		LOEB'S theory of colloid behavior.
Sunlight and Ca metabolism, etc.
ENZYMES
WARBURG: Respiratory ferment.
1926: SUMNER: Crystalline urease.
NORTHROP

SVEDBERG: ultracentrifuge.
    (one aspect in the foundation of Biochemistry.)

ROSE: Amino acids and man.

FLEMING: Penicillin
    ( ANTIBIOTICS )
DOMAGK, STANLEY
Previous spectroscopy STRUCTURE

KUHN: Statistics application (to polymers).

( FLORY, DEBYE, etc.) CAROTHERS
(condensation polymers)
Polyesters
Polyamides

( other polymers)

Vinyl polymers Co-polymers

Polyethylene (and higher olefins)

1930



GEN
ELT/TECH Return to top. 		1930: NORTHROP: Crystalline pepsin.
1931: Crystalline trypsin. ENZYME Chemistry.

Vitamins: ZILVA, EVANS, KARRER, DAM,
DU VIGNEAUD, HAWORTH, etc.
IMMUNOCHEMISTRY
Biochemical Antagonism;
Molecular Disease.

Biochemical Genetics

BIOCHEMISTRY:
Revolution in Methodology.

ANTIBIOTICS:
  • DOMAGK: Prontosil
    SULFA DRUGS
  • STANLEY: Crystalline virus
    ( infective nucleic acid )
1933: HEVESY: Tracer studies.
{ SCHOENHEIMER}
"Dymanic State of Body Constituents."

CORI and CORI: Enzymes in Carbohydrate Metabolism.

1935: KREBS cycle. ENZYME Chemistry

OPARIN: life from primeval environment.
Polymers:
Block and Graft polymers.
Vinyl ethers.
(later (1950's) work of
Ziegler and Natta)
FLORY (in part based upon the work of KUHN):
Condensation polymers.
  • DEBYE (light scattering theory)
  • Physical chemistry of polymers
    • Molecular size
    • Configuration
    Mechanical properties, etc.,
    of polymers

1940



GEN
ELT/TECH Return to top. 		CHEMOTHERAPY

TISELIUS: Electrophoresis

BIOCHEMISTRY---

Revolution in Methodology (based in part on advances in chromatography, spectrophotometry, use of isotopes, and biochemical genetics).

Physical Chemical aspects
STRUCTURE
  • Nucleotides
  • Nucleic Acid
  • Polysaccharides
  • Lipids
  • Polypeptides
  • Proteins
  • Insulin
SYNTHESIS
  • Flavin
  • Adenine
  • dinucleotide
  • Vasopressin
PROTEINS--- Molecular Architecture and Stereochemistry

Pauling -- "alpha helix"

ENZYME Chemistry. (1940's and beyond)
  • Enzymes as tools for analysis and structure determination.
  • Enzyme systems in Intracellular Processes:
    • Mitochondrion
    • Chloroplast
    • Microsomes
  • Isolation of Enzymes:
    • Chromatography
    • Electroconvection
    • Electrophoresis
    • Ion Exchange
    • Partition Methods


    1. Details of citric, pentose, fatty acid and urea cycles.
    2. Enzymatic synthesis:
      • Nucleic acid
      • Lecithin
      • Cephalin
      • Fatty acids
      • Sucrose
      • Lactose
      • Purines
      • Pyrimidines
      • Dinucleotides
    3. Details of enzymatic synthesis--- hemin and cholesterol.
    4. Hundreds of enzymes studied.
    5. Most classical metabolism problems (Protein, Carbohydrate, Fat Metabolism, etc.) solved
    6. Many co-enzymes discovered.
    Studies of PHOTOSYNTHESIS.
ZIEGLER: Catalysts;
Low pressure polyethylene.
NATTA: Stereospecific Polymerization.
Isotactic polymers.

ORGANO
  • Phosphorus
  • Fluorine
  • Sulfur
  • Silicon
ORGANOMETALLIC compounds.

Microwave spectroscopy.

Organic and inorganic REACTION MECHANISMS: ROBINSON, INGOLD, HINSHELWOOD, etc.

1950



GEN
ELT/TECH Return to top. 		1953: PAULING and COREY:
  • Nucleic acid
  • α helix principle
1953: WATSON-CRICK Model

1955: Vitamin B12 structure determined.

1956: Morphine synthesized.

Physical Chemistry of Biological Systems and Materials
  • Kinetics of enzymes
  • Energy transformations and high energy bond
  • Properties and behavior of proteins
  • Myosin contraction
1964: Kevlar discovered (used in aircraft tires, bullet-proof vests, etc.)

1960



GEN
ELT/TECH Return to top. 		1960: Contraceptive pill.

1963: Valium introduced.

1965: Aspartame (Nutrasweet) sugar substitute discovered.

1966: Synthesis of insulin.

1977: Conducting polymers.

1970



GEN
ELT/TECH Return to top. 		1972: Synthesis of vitamin B12.

1978: insulin (via genetic engineering; now the predominant source)

1979: blood substitutes

1985: Buckminsterfullerene (C60)

1980



GEN
ELT/TECH
Return to top. 		-
-

1990



GEN
ELT/TECH
Return to top. 		-