H.C. Brown
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Herbert Charles Brown (May 22, 1912 – December 19, 2004) was an American chemist and recipient of the 1979
Nobel Prize in Chemistry The Nobel Prize in Chemistry () is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outst ...
for his work with
organoborane Organoboron chemistry or organoborane chemistry studies organoboron compounds, also called organoboranes. These chemical compounds combine boron and carbon; typically, they are organic derivatives of borane (BH3), as in the trialkyl boranes. Or ...
s.


Life and career

Brown was born Herbert Brovarnik in
London London is the Capital city, capital and List of urban areas in the United Kingdom, largest city of both England and the United Kingdom, with a population of in . London metropolitan area, Its wider metropolitan area is the largest in Wester ...
, to Ukrainian
Jewish Jews (, , ), or the Jewish people, are an ethnoreligious group and nation, originating from the Israelites of History of ancient Israel and Judah, ancient Israel and Judah. They also traditionally adhere to Judaism. Jewish ethnicity, rel ...
immigrants from
Zhitomir Zhytomyr ( ; see #Names, below for other names) is a city in the north of the western half of Ukraine. It is the Capital city, administrative center of Zhytomyr Oblast (Oblast, province), as well as the administrative center of the surrounding ...
, Pearl (''
née The birth name is the name of the person given upon their birth. The term may be applied to the surname, the given name or to the entire name. Where births are required to be officially registered, the entire name entered onto a births registe ...
'' Gorinstein) and Charles Brovarnik, a hardware store manager and carpenter. His family moved to
Chicago Chicago is the List of municipalities in Illinois, most populous city in the U.S. state of Illinois and in the Midwestern United States. With a population of 2,746,388, as of the 2020 United States census, 2020 census, it is the List of Unite ...
in June 1914, when he was two years old. Brown attended
Crane Junior College Malcolm X College, one of the City Colleges of Chicago, is a two-year college located on the Near West Side of Chicago, Illinois. It was founded as Crane Junior College in 1911 and was the first of the City Colleges. Crane ceased operation during ...
in Chicago, where he met Sarah Baylen, whom he would later marry. The college was under threat of closing, and Brown and Baylen transferred to
Wright Junior College Wilbur Wright College, formerly known as Wright Junior College, is a public community college in Chicago. Part of the City Colleges of Chicago system, it offers two-year associate's degrees, as well as occupational training in IT, manufacturing, ...
. In 1935 he left Wright and that autumn entered the
University of Chicago The University of Chicago (UChicago, Chicago, or UChi) is a Private university, private research university in Chicago, Illinois, United States. Its main campus is in the Hyde Park, Chicago, Hyde Park neighborhood on Chicago's South Side, Chic ...
, completing two years of studies in three quarters to earn a B.S. in 1936. That same year, he became a naturalized
United States citizen Citizenship of the United States is a legal status that entails Americans with specific rights, duties, protections, and benefits in the United States. It serves as a foundation of fundamental rights derived from and protected by the Constitu ...
, and began graduate studies at Chicago. On February 6, 1937, Brown married Baylen, whom he would later credit with sparking an interest in
hydrides In chemistry, a hydride is formally the anion of hydrogen (H−), a hydrogen ion with two electrons. In modern usage, this is typically only used for ionic bonds, but it is sometimes (and has been more frequently in the past) applied to all co ...
of
boron Boron is a chemical element; it has symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the boron group it has three ...
that would eventually lead to the work for which he, together with
Georg Wittig Georg Wittig (; 16 June 1897 – 26 August 1987) was a German chemist who reported a method for synthesis of alkenes from aldehydes and ketones using compounds called phosphonium ylides in the Wittig reaction. He shared the Nobel Prize i ...
, would be awarded the Nobel prize in Chemistry in 1979, and the following year received his degree as
Ph.D. A Doctor of Philosophy (PhD, DPhil; or ) is a terminal degree that usually denotes the highest level of academic achievement in a given discipline and is awarded following a course of graduate study and original research. The name of the deg ...
Unable to find a position in industry, he decided to accept a
postdoctoral A postdoctoral fellow, postdoctoral researcher, or simply postdoc, is a person professionally conducting research after the completion of their doctoral studies (typically a PhD). Postdocs most commonly, but not always, have a temporary acade ...
position, beginning his academic career. He became an instructor at Chicago in 1939, and held the position for four years before moving to
Wayne University Wayne State University (WSU) is a public research university in Detroit, Michigan, United States. Founded in 1868, Wayne State consists of 13 schools and colleges offering approximately 375 programs. It is Michigan's third-largest university w ...
in
Detroit Detroit ( , ) is the List of municipalities in Michigan, most populous city in the U.S. state of Michigan. It is situated on the bank of the Detroit River across from Windsor, Ontario. It had a population of 639,111 at the 2020 United State ...
as an
assistant professor Assistant professor is an academic rank just below the rank of an associate professor used in universities or colleges, mainly in the United States, Canada, Japan, and South Korea. Overview This position is generally taken after earning a doct ...
. In 1946, he was promoted to
associate professor Associate professor is an academic title with two principal meanings: in the North American system and that of the ''Commonwealth system''. In the ''North American system'', used in the United States and many other countries, it is a position ...
, and the following year became a
professor Professor (commonly abbreviated as Prof.) is an Academy, academic rank at university, universities and other tertiary education, post-secondary education and research institutions in most countries. Literally, ''professor'' derives from Latin ...
of
inorganic chemistry Inorganic chemistry deals with chemical synthesis, synthesis and behavior of inorganic compound, inorganic and organometallic chemistry, organometallic compounds. This field covers chemical compounds that are not carbon-based, which are the subj ...
at
Purdue University Purdue University is a Public university#United States, public Land-grant university, land-grant research university in West Lafayette, Indiana, United States, and the flagship campus of the Purdue University system. The university was founded ...
in 1947 and joined the Beta Nu chapter of
Alpha Chi Sigma Alpha Chi Sigma () is a professional fraternity specializing in the fields of the chemical sciences. It has both collegiate and professional chapters throughout the United States consisting of both men and women and numbering more than 78,000 m ...
there in 1960. He held the position of
Professor Emeritus ''Emeritus/Emerita'' () is an honorary title granted to someone who retirement, retires from a position of distinction, most commonly an academic faculty position, but is allowed to continue using the previous title, as in "professor emeritus". ...
from 1978 until his death in 2004. The ''Herbert C. Brown Laboratory of Chemistry'' was named after him on Purdue University's campus. He was an honorary member of the International Academy of Science, Munich. During
World War II World War II or the Second World War (1 September 1939 – 2 September 1945) was a World war, global conflict between two coalitions: the Allies of World War II, Allies and the Axis powers. World War II by country, Nearly all of the wo ...
, while working with
Hermann Irving Schlesinger Hermann Irving Schlesinger (October 11, 1882 – October 3, 1960) was an American inorganic chemist, working in boron chemistry. He and Herbert C. Brown discovered sodium borohydride in 1940 and both were involved in the further development of ...
, Brown discovered a method for producing
sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula (sometimes written as ). It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodi ...
(NaBH4), which can be used to produce
borane Borane is an inorganic compound with the chemical formula . Because it tends to dimerize or form adducts, borane is very rarely observed. It normally dimerizes to diborane in the absence of other chemicals. It can be observed directly as a c ...
s, compounds of
boron Boron is a chemical element; it has symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the boron group it has three ...
and
hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...
. His work led to the discovery of the first general method for producing asymmetric pure
enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...
s. The elements found as initials of his name H, C and B were his working field. In 1969, he was awarded the
National Medal of Science The National Medal of Science is an honor bestowed by the President of the United States to individuals in science and engineering who have made important contributions to the advancement of knowledge in the fields of behavioral science, behavior ...
. Brown was quick to credit his wife Sarah with supporting him and allowing him to focus on creative efforts by handling finances, maintaining the house and yard, etc. According to Brown, after receiving the Nobel prize in
Stockholm Stockholm (; ) is the Capital city, capital and List of urban areas in Sweden by population, most populous city of Sweden, as well as the List of urban areas in the Nordic countries, largest urban area in the Nordic countries. Approximately ...
, he carried the medal and she carried the US$100,000 award. In 1971, he received the Golden Plate Award of the
American Academy of Achievement The American Academy of Achievement, colloquially known as the Academy of Achievement, is a nonprofit educational organization that recognizes some of the highest-achieving people in diverse fields and gives them the opportunity to meet one ano ...
. He was inducted into the
Alpha Chi Sigma Alpha Chi Sigma () is a professional fraternity specializing in the fields of the chemical sciences. It has both collegiate and professional chapters throughout the United States consisting of both men and women and numbering more than 78,000 m ...
Hall of Fame in 2000. He died December 19, 2004, at a
hospital A hospital is a healthcare institution providing patient treatment with specialized Medical Science, health science and auxiliary healthcare staff and medical equipment. The best-known type of hospital is the general hospital, which typically ...
in
Lafayette, Indiana Lafayette ( ) is a city in and is the county seat of Tippecanoe County, Indiana, United States, located northwest of Indianapolis and southeast of Chicago. According to the 2020 United States census, 2020 census, the population of Lafayette ...
after a
heart attack A myocardial infarction (MI), commonly known as a heart attack, occurs when Ischemia, blood flow decreases or stops in one of the coronary arteries of the heart, causing infarction (tissue death) to the heart muscle. The most common symptom ...
. His wife died May 29, 2005, aged 89.


Research

As a doctoral student at the
University of Chicago The University of Chicago (UChicago, Chicago, or UChi) is a Private university, private research university in Chicago, Illinois, United States. Its main campus is in the Hyde Park, Chicago, Hyde Park neighborhood on Chicago's South Side, Chic ...
, Herbert Brown studied the reactions of
diborane Diborane(6), commonly known as diborane, is the chemical compound with the formula . It is a highly toxic, colorless, and pyrophoric gas with a repulsively sweet odor. Given its simple formula, borane is a fundamental boron compound. It has att ...
, B2H6. Hermann Irving Schlesinger's laboratory at the University of Chicago was one of two laboratories that prepared diborane. It was a rare compound that was only prepared in small quantities. Schlesinger was researching the reactions of diborane to understand why the simplest hydrogen-boron compound is B2H6 instead of BH3. When Brown started his own research, he observed the reactions of diborane with
aldehydes In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
,
ketones In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
,
esters In chemistry, an ester is a chemical compound, compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds c ...
, and acid chlorides. He discovered that diborane reacts with aldehydes and ketones to produce dialkoxyboranes, which are
hydrolyzed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...
by water to produce
alcohols In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol ...
. Until this point, organic chemists did not have an acceptable method of reducing
carbonyls In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such as aldehydes, ...
under mild conditions. Yet Brown's Ph.D. thesis published in 1939 received little interest. Diborane was too rare to be useful as a synthetic reagent. In 1939, Brown became the research assistant in Schlesinger's laboratory. In 1940, they began to research volatile, low molecular weight uranium compounds for the
National Defense Research Committee The National Defense Research Committee (NDRC) was an organization created "to coordinate, supervise, and conduct scientific research on the problems underlying the development, production, and use of mechanisms and devices of warfare" in the U ...
. Brown and Schlesinger successfully synthesized volatile uranium(IV) borohydride, which had a molecular weight of 298. The laboratory was asked to provide a large amount of the product for testing, but diborane was in short supply. They discovered that it could be formed by reacting
lithium hydride Lithium hydride is an inorganic compound with the formula Li H. This alkali metal hydride is a colorless solid, although commercial samples are grey. Characteristic of a salt-like (ionic) hydride, it has a high melting point, and it is not solub ...
with
boron trifluoride Boron trifluoride is the inorganic compound with the formula . This pungent, colourless, and toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure and bonding The g ...
in
ethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs to the ether class of o ...
, allowing them to produce the chemical in larger quantities. This success was met with several new problems. Lithium hydride was also in short supply, so Brown and Schlesinger needed to find a procedure that would allow them to use
sodium hydride Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in co ...
instead. They discovered that sodium hydride and methyl borate reacted to produce sodium trimethoxyborohydride, which was viable as a substitute for the lithium hydride. Soon they were informed that there was no longer a need for uranium borohydride, but it appeared that sodium borohydride could be useful in generating
hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...
. They began to look for a cheaper synthesis and discovered that adding methyl borate to sodium hydride at 250° produced sodium borohydride and sodium methoxide. When
acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
was used in an attempt to separate the two products, it was discovered that sodium borohydride reduced the acetone. Sodium borohydride is a mild
reducing agent In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are common reducing agents include hydrogen, carbon ...
that works well in reducing aldehydes, ketones, and acid chlorides. Lithium aluminum hydride is a much more powerful reducing agent that can reduce almost any
functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
. When Brown moved to
Purdue University Purdue University is a Public university#United States, public Land-grant university, land-grant research university in West Lafayette, Indiana, United States, and the flagship campus of the Purdue University system. The university was founded ...
in 1947, he worked to find stronger
borohydrides Borohydride refers to the anion , which is also called tetrahydroborate or more commonly tetrahydrobiopterin, and its salts. Borohydride or hydroborate is also the term used for compounds containing , where ''n'' is an integer from 0 to 3, for ex ...
and milder aluminum hydrides that would provide a spectrum of reducing agents. The team of researchers at Purdue discovered that changing the metal ion of the borohydride to
lithium Lithium (from , , ) is a chemical element; it has chemical symbol, symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard temperature and pressure, standard conditions, it is the least dense metal and the ...
,
magnesium Magnesium is a chemical element; it has Symbol (chemistry), symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 ...
, or
aluminum Aluminium (or aluminum in North American English) is a chemical element; it has chemical symbol, symbol Al and atomic number 13. It has a density lower than that of other common metals, about one-third that of steel. Aluminium has ...
increases the reducing ability. They also found that introducing
alkoxy In chemistry, the alkoxy group is an alkyl group which is Single bond, singularly bonded to oxygen; thus . Denoted usually with apostrophe('). The range of alkoxy groups is vast, the simplest being methoxy (). An ethoxy group () is found in the ...
substituents to the aluminum hydride decreases the reducing ability. They successfully developed a full spectrum of reducing agents. While researching these reducing agents, Brown's coworker, Dr. B. C. Subba Rao, discovered an unusual reaction between sodium borohydride and
ethyl oleate Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless oil although degraded samples can appear yellow. Use and occurrence Additive Ethyl oleate is used by compounding pharmacies as a vehicle f ...
. The borohydride added hydrogen and boron to the carbon-carbon
double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...
in the ethyl oleate. The organoborane product could then be
oxidized Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...
to form an alcohol. This two-step reaction is now called hydroboration-oxidation and is a reaction that converts
alkenes In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...
into anti-Markovnikov alcohols.
Markovnikov's rule In organic chemistry, Markovnikov's rule or Markownikoff's rule describes the outcome of some addition reactions. The rule was formulated by Russian chemist Vladimir Markovnikov in 1870. Explanation The rule states that with the addition of a ...
states that, in adding hydrogen and a
halide In chemistry, a halide (rarely halogenide) is a binary chemical compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative (or more electropositive) than the halogen, to make a fl ...
or
hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
group to a carbon-carbon double bond, the hydrogen is added to the less-substituted carbon of the bond and the hydroxyl or halide group is added to the more-substituted carbon of the bond. In hydroboration-oxidation, the opposite addition occurs.


See also

*
List of Jewish Nobel laureates Of the 965 individual recipients of the Nobel Prize and the Nobel Memorial Prize in Economic Sciences between 1901 and 2023, at least 216 have been Jews or people with at least one Jewish parent, representing 22% of all recipients. Jews constitut ...


References


External links

*
Herbert Brown obituary
in
Chemical & Engineering News ''Chemical & Engineering News'' (''C&EN'') is a weekly news magazine published by the American Chemical Society (ACS), providing professional and technical news and analysis in the fields of chemistry and chemical engineering.Herbert Brown obituary
in
USA Today ''USA Today'' (often stylized in all caps) is an American daily middle-market newspaper and news broadcasting company. Founded by Al Neuharth in 1980 and launched on September 14, 1982, the newspaper operates from Gannett's corporate headq ...

National Academy of Sciences Biographical MemoirNobel Lecture
1979 {{DEFAULTSORT:Brown, Herbert C. 1912 births 2004 deaths Nobel laureates in Chemistry British Nobel laureates American Nobel laureates Jewish Nobel laureates 20th-century English Jews English people of Ukrainian-Jewish descent English emigrants to the United States American people of Ukrainian-Jewish descent Jewish American scientists Jewish chemists American inorganic chemists Stereochemists Purdue University faculty Wayne State University faculty University of Chicago alumni National Medal of Science laureates Wilbur Wright College alumni