A carboxylic acid ester. R and R' denote any alkyl or aryl group

Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol.^[1] Esters are usually derived from an inorganic acid or organic acid in which at least one -OH (hydroxyl) group is replaced by an -O-alkyl (alkoxy) group, and most commonly from carboxylic acids and alcohols. That is, esters are formed by condensing an acid with an alcohol.

Esters are ubiquitous. Most naturally occurring fats and oils are the fatty acid esters of glycerol. Esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important plastics, with monomers linked by ester moieties.

Nomenclature [link]

Etymology [link]

The word 'ester' was coined in 1848 by German chemist Leopold Gmelin.^[2]], probably as a contraction of the german Essigäther - acetic ether.

IUPAC nomenclature of Esters [link]

Ester names are derived from the parent alcohol and the parent acid, where the latter may be an organic or an inorganic acid. Esters derived from the simplest carboxylic acids are commonly named according to the more traditional, so-called "trivial names" e.g. as formate, acetate, propionate, and butyrate, as opposed to the IUPAC nomenclature methanoate, ethanoate, propanoate and butanoate. Esters derived from more complex carboxylic acids are, on the other hand, more frequently named using the systematic IUPAC name, based on the name for the acid followed by the suffix -oate. For example the ester hexyl octanoate, also known under the trivial name hexyl caprylate, has the formula CH₃(CH₂)₆CO₂(CH₂)₅CH₃.

The chemical formulas of organic esters are typically written in the format of RCO₂R', where R and R' are the hydrocarbon parts of the carboxylic acid and alcohol, respectively. For example butyl acetate, derived from butanol and acetic acid would be written CH₃CO₂C₄H₉. Alternative presentations are common including BuOAc and CH₃COOC₄H₉.

Cyclic esters are called lactones, regardless of whether they are derived from an organic or an inorganic acid. One example of a (organic) lactone is gamma-valerolactone.

Orthoesters [link]

An uncommon class of organic esters are the orthoesters, which have the formula RC(OR')₃. Triethylorthoformate (HC(OC₂H₅)₃) is derived, in terms of its name (but not its synthesis) from orthoformic acid (HC(OH)₃) and ethanol.

"Inorganic esters" [link]

A phosphoric acid ester

Ester is a general term for the product derived from the condensation of an acid and an alcohol. Thus, the nomenclature extends to inorganic oxo acids, e.g. phosphoric acid, sulfuric acid, nitric acid and boric acid. For example, triphenyl phosphate is the ester derived from phosphoric acid and phenol. Organic carbonates, such as ethylene carbonate, are derived from carbonic acid and ethylene glycol.

Structure and bonding [link]

Esters contain a carbonyl center, which gives rise to 120°C-C-O and O-C-O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C-O-C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides.^[3] The pKa of the alpha-hydrogens on esters is around 25.^[4]

Physical properties and characterization [link]

Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently esters are more volatile than carboxylic acids of similar molecular weight.^[3]

Characterization and analysis [link]

Esters are usually identified by gas chromatography, taking advantage of their volatility. IR spectra for esters feature an intense sharp band in the range 1730–1750 cm⁻¹ assigned to ν_C=O. This peak changes depending on the functional groups attached to the carbonyl. For example, a benzene ring or double bond in conjugation with the carbonyl will bring the wavenumber down about 30 cm⁻¹.

Applications and occurrence [link]

Esters are widespread in nature and are widely used in industry. In nature, fats are, in general, triesters derived from glycerol and fatty acids.^[5] Esters are responsible for the aroma of many fruits, including apples, pears, bananas, pineapples, and strawberries.^[6] Several billion kilograms of polyesters are produced industrially annually, important products being polyethylene terephthalate, acrylate esters, and cellulose acetate.^[7]

Preparation [link]

Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor. This leads to their extensive use in the fragrance and flavor industry. Ester bonds are also found in many polymers.

Esterification of carboxylic acids[link]

The classic synthesis is the Fischer esterification, which involves treating a carboxylic acid with an alcohol in the presence of a dehydrating agent:

RCO₂H + R'OH RCO₂R' + H₂O

The equilibrium constant for such reactions is about 5 for typical esters, e.g., ethyl acetate.^[8] but the reaction is slow in the absence of a catalyst. Sulfuric acid is a typical catalyst for this reaction. Many other acids are also used such as polymeric sulfonic acids. Since esterification is highly reversible, the yield of the ester can be improved using Le Chatelier's principle:

• using the alcohol in large excess (i.e., as a solvent)
• using a dehydrating agent: sulfuric acid not only catalyzes the reaction but sequesters water (a reaction product). Other drying agents such as molecular sieves are also effective.
• removal of water by physical means such as distillation as a low-boiling azeotropes with toluene, in conjunction with a Dean-Stark apparatus.

Reagents are known that drive the dehydration of mixtures of alcohols and carboxylic acids. One example is the Steglich esterification, which is a method of forming esters under mild conditions. The method is popular in peptide synthesis, where the substrates are sensitive to harsh conditions like high heat. DCC (dicyclohexylcarbodiimide) is used to activate the carboxylic acid to further reaction. DMAP (4-dimethylaminopyridine) is used as an acyl-transfer catalyst.^[9]

Another method for the dehydration of mixtures of alcohols and carboxylic acids is the Mitsunobu reaction:

RCO₂H + R'OH + P(C₆H₅)₃ + R₂N₂ → RCO₂R' + OP(C₆H₅)₃ + R₂N₂H₂

Carboxylic acids can be esterified using diazomethane:

RCO₂H + CH₂N₂ → RCO₂CH₃ + N₂

Using this diazomethane, mixtures of carboxylic acids can be converted to their methyl esters in near quantitative yields, e.g., for analysis by gas chromatography. The method is useful in specialized organic synthetic operations but is considered too expensive for large scale applications.

Alcoholysis of acyl chlorides and acid anhydrides [link]

Alcohols react with acyl chlorides and acid anhydrides to give esters:

RCOCl + R'OH → RCO₂R' + HCl

(RCO)₂O + R'OH → RCO₂R' + RCO₂H

The reactions are irreversible simplifying work-up. Since acyl chlorides and acid anhydrides also react with water, anhydrous conditions are preferred. The analogous acylations of amines to give amides are less sensitive because amines are stronger nucleophiles and react more rapidly than does water. This method is employed only for laboratory-scale procedures, as it is expensive.

Alkylation of carboxylate salts[link]

Although not widely employed for esterifications, salts of carboxylate anions can be alkylating agent with alkyl halides to give esters. In the case that an alkyl chloride is used, an iodide salt can catalyze the reaction (Finkelstein reaction). The carboxylate salt is often generated in situ. In difficult cases, the silver carboxylate may be used, since the silver ion coordinates to the halide aiding its departure and improving the reaction rate. This reaction can suffer from anion availability problems and, therefore, can benefit from the addition of phase transfer catalysts or highly polar aprotic solvents such as DMF.

Transesterification[link]

Transesterification, which involves changing one ester into another one, is widely practiced:

RCO₂R' + CH₃OH → RCO₂CH₃ + R'OH

Like the hydrolysction, transesterification is catalysed by acids and bases. The reaction is widely used for degrading triglycerides, e.g. in the production of fatty acid esters and alcohols. Poly(ethyleneterephthalate) is produced by the transesterification of dimethyl terephthalate and ethylene glycol:^[7]

(C₆H₄)(CO₂CH₃)₂ + 2 C₂H₄(OH)₂ → 1/n {(C₆H₄)(CO₂)₂(C₂H₄)}_n + 2 CH₃OH

Carbonylation[link]

Alkenes undergo "hydroesterification" in the presence of metal carbonyl catalysts. Esters of propionic acid are produced commercially by this method:

C₂H₄ + ROH + CO → C₂H₅CO₂R

The carbonylation of methanol yields methyl formate, which the main commercial source of formic acid. The reaction is catalyzed by sodium methoxide:

CH₃OH + CO → CH₃O₂CH

Addition of carboxylic acids to alkenes[link]

In the presence of palladium-based catalysts, ethylene, acetic acid, and oxygen react to give vinyl acetate:

C₂H₄ + CH₃CO₂H + 1/2 O₂ → C₂H₃O₂CCH₃ + H₂O

Direct routes to this same ester are not possible because vinyl alcohol is unstable.

Other methods [link]

• Favorskii rearrangement of α-haloketones in presence of base
• Baeyer-Villiger oxidation of ketones with peroxides.
• Pinner reaction of nitriles with an alcohol.
• Nucleophilic abstraction of a metal-acyl complex.

Reactions [link]

Esters react with nucleophiles at the carbonyl carbonyl carbon. The carbonyl is weakly electrophilic but is attacked by strong nucleophilies (amines, alkoxides, hydride sources, organolithium compounds, etc.). The C-H bonds adjacent to the carbonyl are weakly acidic but undergo deprotonation with strong bases. This process is the one that usually initiates condensation reactions. The carbonyl oxygen is weakly basic (less so than in amides) but forms adducts.

Addition of nucleophiles at carbonyl[link]

Esterification is a reversible reaction. Esters undergo hydrolysis under acid and basic conditions. Under acidic conditions, the reaction is the reverse reaction of the Fischer esterification. Under basic conditions, hydroxide acts as a nucleophile, while an alkoxide is the leaving group. This reaction, saponification, is the basis of soap making.

The alkoxide group may also be displaced by stronger nucleophiles such as ammonia or primary or secondary amines to give amides:

RCO₂R' + NH₂R" → RCONHR" + R'OH

This reaction is not usually reversible. Hydrazines and hydroxylamine can be used in place of amines. Esters can be converted to isocyanates through intermediate hydroxamic acids in the Lossen rearrangement.

Sources of carbon nucleophiles, e.g., Grignard reagents and organolithium compounds, add readily to the carbonyl.

Reduction [link]

Compared to ketones and aldehydes, esters are relatively resistant to reduction. The introduction of catalytic hydrogenation in the early part of the 20th century was a breakthrough; esters of fatty acids are hydrogenated to fatty alcohols.

RCO₂R' + 2 H₂ → RCH₂OH + R'OH

A typical catalyst is copper chromite. Prior to the development of catalytic hydrogenation, esters were reduced on a large scale using the Bouveault-Blanc reduction. This method, which is largely obsolete, uses sodium in the presence of proton sources.

Especially for fine chemical syntheses, lithium aluminium hydride is used to reduce esters to two primary alcohols. The related reagent sodium borohydride is slow in this reaction. DIBAH reduces esters to aldehydes.^[10]

Claisen condensation and related reactions[link]

As for ketones and aldehydes, the hydrogen atoms on the carbon adjacent ("α to") the carboxyl group in esters are sufficiently acidic to undergo deprotonation, which in turn leads to a variety of useful reactions. Deprotonation requires relatively strong bases, such as alkoxides. Deprotonation gives a nucleophilic enolate, which can further react, e.g., the Claisen condensation and its intramolecular equivalent, the Dieckmann condensation. This conversion is exploited in the malonic ester synthesis, wherein the diester of malonic acid reacts with an electrophile (e.g., alkyl halide), and is subsequently decarboxylated.

Other reactions [link]

• Phenyl esters react to hydroxyarylketones in the Fries rearrangement.
• Specific esters are functionalized with an α-hydroxyl group in the Chan rearrangement.
• Esters with β-hydrogen atoms can be converted to alkenes in ester pyrolysis.

Protecting groups [link]

As a class, esters serve as protecting groups for carboxylic acids. Protecting a carboxylic acid is useful in peptide synthesis, to prevent self-reactions of the bifunctional amino acids. Methyl and ethyl esters are commonly available for many amino acids; the t-butyl ester tends to be more expensive. However, t-butyl esters are particularly useful because, under strongly acidic conditions, the t-butyl esters undergo elimination to give the carboxylic acid and isobutene, simplifying work-up.

List of ester odorants [link]

Many esters have distinctive fruit-like odors, which has led to their commonplace use in artificial flavorings and fragrances.

See also[link]

• Cyanate ester
• Oligoester
• Polyolester
• Transesterification
• Transamidification

References [link]

External links [link]

• An introduction to esters
• Molecule of the month: Ethyl acetate and other esters
• An example of esters commercial application

Ester Renay Dean (born April 15, 1986) is an American singer and songwriter, and record producer signed to Roc Nation. She is most notable for her dual appearance on Rio: Music From The Motion Picture (2011) and her 2009 US hit single "Drop It Low", which featured singer Chris Brown.

Dean has also written songs with many artists including Christina Aguilera, Katy Perry, Beyoncé, Mary J. Blige, Nicki Minaj, Kelly Clarkson, Ciara, Nicole Scherzinger, Usher, Kelly Rowland, Girlicious, Rihanna, R. Kelly, Britney Spears, Soulja Boy Tell 'Em, Pia Toscano, Tinie Tempah, Lil Wayne, Machine Gun Kelly and recently Shakira.

In 2012 Dean also lent her voice to Ice Age as one of the characters, as well to the film Pitch Perfect and the soundtrack.

Biography[link]

1986-2010: Early life and career beginnings[link]

Tulsa, Oklahoma where Dean grew up.

Ester Dean was born in Muskogee, Oklahoma in 1986, but lived in Tulsa, Oklahoma, then in her late teens, she moved to Omaha, Nebraska. After graduating from Omaha North High School, she moved to Atlanta, Georgia, until relocating to Los Angeles, California. In an interview Dean spoke on her family life,

Oh, my whole family can sing. When I was growing up, I said I was going to be a chef. And my cousin was like, “No you aren't. You're going to sing.” And I'm like, “No, I'm not. I'm going to be a chef. And that's it.” And they're like, “No, you're going to sing.” And I said, “Okay, well I'll sing and get the money and set-up a restaurant.” My mom, she used to do gospel plays. And we used to go on the road with her and perform in the choir, so I grew up watching her star in these gospel plays. And it just showed, like, “Oh my God, I want to do this or do something like this.” I noticed how I started to get jealous when they used to pick other little girls to sing certain parts. And I'd be like, “Well, I can sing that better.” Or we'd be in their studio and I'm like, “I want to sing in a studio.” When I was really young, that childhood jealousy and seeing what I really wanted – I used to sing into anything I could hear myself back on. That's what I'd do. Even if it was karaoke, I just wanted to be heard, you know? I believe my mom wanted me to be a star and an artist. I think it trickles down. Sometimes it takes them to want it for you to do it.^[1][2]

When Dean relocated to Los Angeles, California, she became a successful songwriter, and was introduced to Polow da Don, and later signed to Zone 4 Records/Interscope Records. During her tenure, Dean has amassed a catalog of songs she has written or co-written for other artists, such as Britney Spears, Rihanna, Christina Aguilera, Monica, Keri Hilson, Keyshia Cole, Kelly Rowland, Girlicious, Katy Perry, Trey Songz, Kelly Clarkson, Ciara, Usher, Chris Brown, Nicki Minaj, Pia Toscano, Ginuwine, Teyana Taylor, Scotty McCreery, Beyoncé Knowles, and Mary J. Blige, among others.

Dean recorded and released her first single, "Drop It Low" which features singer Chris Brown, from the LeBron James documentary, More Than a Game (2009), which peaked at #38 on the US Billboard Hot 100, becoming her first US Top 40 single. The song received positive reviews, and the song was remixed by artists such as Lil Wayne, Trey Songz and Diddy. Dean has co-written songs featured on the Step Up 3D Original Motion Picture Soundtrack (2010) and Burlesque: Original Motion Picture Soundtrack (2010).

2011-Present: First studio album and Roc Nation[link]

Throughout 2011 Dean carried on song writing while working on her album, she co-wrote "Super Bass", for Nicki Minaj's debut album Pink Friday (2010).^[3] has gone on to achieve the position of number three on the Hot 100.^[4] The song's title is included as part of the title of a UK Deluxe edition of the album, Pink Friday (Super Bass Edition).^[5] Dean has a dual appearance on Rio: Music From The Motion Picture (2011) with "Let Me Take You To Rio" and "Take You To Rio". Dean is featured on the song "Invincible", the second single by American rapper Machine Gun Kelly's debut album. The song has been used in a HTC ReZound ad and also served as one of several theme songs for WrestleMania XXVIII.

Talking on her debut album Ester said "I did not want to be an artist because I was afraid" Dean confesses, "I had tried that before but I learned I had to lose when I weighed only , it poisoned me, however Polow wanted to embrace everything about me and welcomed me to his family just like me ".^[6] Dean is working on her debut studio album set to be released in early 2012. Ester told billboard "We're working on picking songs right now," Ester tells The Juice. Ester is shooting for a sound that suits her unique voice, which she calls "hard" and "raspy."^[7] In January 2012 Dean took to twitter to announce that she has signed to Roc Nation “I’m so Grateful 4 my Team Past and Present! Bringing in the New Year with my new Team @RocNation 2012,”^[8] She has worked with Stargate on six of the album's tracks.^[9] Gimme Money featuring Nicki Minaj was released online in February 2012 through Dean's official Twitter. Dean tweeted “If you guys Love Gimmie Money ft Nicki Minaj as my Single let’s get it Trending #GimmieMoney”.^[10] Dean has also picked 10 tracks that will be featured on her debut album.^[11]

Dean made an appearance in Ice Age: Continental Drift. "I'm just excited," Dean says of playing her character, the Sloth Siren. "On August 23, I go put my voice down. And my character gets to sing." Ester is one of many musicians in the Ice Age: Continental Drift cast. Drake, Nicki Minaj, Queen Latifah and Jennifer Lopez are lending their voices to the film.^[7]

For her album, Dean has been reported to be working with rapper Nicki Minaj and Roc Nation signed Alexis Jordan.^[12][13] There is talk of calling the album "UnderESTAmated."^[14]

Artistry[link]

Songwriting style[link]

In a 2012 article in The New Yorker, Dean described her preferred method of songwriting: "I go into the booth and I scream and I sing and I yell, and sometimes it's words but most time [sic] it's not...and I just see when I get this little chill [on her upper arm, below the shoulder] and then I'm, like, 'Yeah, that's the hook.'"^[15]

Discography[link]

Singles[link]

Guest Vocals[link]

Filmography[link]

References[link]

External links[link]

• Official website
• Ester Dean on Myspace
• Ester Dean on Twitter

George Kelly Barnes
Mugshot of George "Machine Gun Kelly" Barnes
Born	(1895-07-18)July 18, 1895 Memphis, Tennessee, U.S.
Died	July 18, 1954(1954-07-18) (aged 59) Leavenworth Federal Penitentiary, Leavenworth, Kansas, U.S.
Charge(s)	Conspiracy to kidnap and bank robbing
Occupation	Gangster, bootlegger and businessman
Spouse	Kathryn Kelly

George Celino Barnes (July 18, 1895 – July 18, 1954), better known as "Machine Gun Kelly", was an American gangster during the prohibition era.^[1][2] His nickname came from his favorite weapon, a Thompson submachine gun. His most famous crime was the kidnapping of oil tycoon and businessman Charles Urschel in July 1933 for which he, and his gang, earned $200,000 ransom. Unfortunately, their victim had collected and left considerable evidence that assisted the subsequent FBI investigation that eventually led to Kelly's arrest in Memphis, Tennessee on September 26, 1933.^[2] His crimes also included bootlegging and armed robbery.

Career[link]

During the Prohibition era of the 1920s and 1930s Kelly worked as a bootlegger for himself as well as a colleague. After a short time, and several run-ins with the local Memphis police, he decided to leave town and head west with his girlfriend. To protect his family and escape law enforcement officers, he changed his name to George R. Kelly.^[3] He continued to commit smaller crimes and bootlegging. He was arrested in Tulsa, Oklahoma, for smuggling liquor onto an Indian Reservation in 1928 and sentenced for three years to Leavenworth Penitentiary, Kansas, beginning February 11, 1928. He was reportedly a model inmate and was released early. Shortly thereafter, Kelly married Kathryn Thorne, who purchased Kelly’s first machine gun and went to great lengths to familiarize his name in the underground crime circles. She was known to hand out the expended .45cal cartridge casings from his Tommy Gun as souvenirs. Some historians claim that Kathryn even went so far as to plot some small bank robberies.^{[citation needed]}

George "Machine Gun" Kelly is led from Shelby County Jail enroute to the Memphis airport and Oklahoma City for his trial for the kidnapping of Charles F. Urschel, October 2, 1933

Nonetheless, Kelly’s last criminal activity proved disastrous when he kidnapped a wealthy Oklahoma City resident, Charles F. Urschel and his friend Walter R. Jarrett. Urschel, having been blindfolded, made sure to foil his kidnappers by noting all possible evidence of his experience such as background sounds, counting footsteps and leaving fingerprints on every surface in reach. This in turn proved invaluable for the FBI in their investigation, as they learned that Urschel had been held in Paradise, Texas.

Machine Gun Kelly's hideout at 1408 Rayner Street in Memphis, Tennnessee (2010)

An investigation conducted at Memphis disclosed that after 56 days on the run, the Kellys were staying at the residence of J.C. Tichenor. Special Agents from Birmingham, Alabama, headed by Special Agent in Charge, William "ash" Rorer, were immediately dispatched to Memphis on the orders of J. Edgar Hoover, where, in the early morning hours of September 26, 1933 a raid was conducted, led by agent Rorer. George and Kathryn Kelly were taken into custody and Memphis police officers Sergeant William Raney and officer Thomas Waterson. Caught without a weapon, George Kelly supposedly cried, "Don’t shoot, G-Men! Don’t shoot, G-Men!" as he surrendered to FBI Agents. The term (which had applied to all federal investigators, meaning simply 'Government Men') became synonymous with FBI Agents. Reports of the raid, however, indicate that George Kelly came to the door, dropped his pistol and said, "Okay, boys, I’ve been waiting for you all night." Recent research revealed a 1933 newspaper interview with one of the federal agents at the arrest. He commented that, upon their arrest, Kathryn Kelly put her arms around George and said, "These G-men will never leave us alone." The FBI press machine generated the G-Man story to build its own reputation.^[4] The arrest of the Kellys, however, was overshadowed by the escape of John Dillinger's gang from Michigan City, Indiana.

In October 1933, George and Kathryn Kelly were convicted and sentenced to life imprisonment. The trial was held at the Post Office, Courthouse and Federal Office Building in Oklahoma City. Kathryn Kelly and her mother had all charges dropped and were released in 1958 from prison in Cincinnati.

The kidnapping of Urschel and the two trials that resulted were historic in several ways: 1) they were the only federal criminal trials in the United States in which moving cameras were allowed to film; 2) the first kidnapping trials after the passage of the so-called Lindbergh Law, which made kidnapping a federal crime; 3) the first major case solved by J. Edgar Hoover’s evolving and powerful FBI. For that, Kelly got sent into Alcatraz; 4) the first crime in which defendants were transported by airplane. At the time, it was the largest ransom ever paid in the United States.

Death[link]

His gravestone marked "George B. Kelley"

Machine Gun Kelly spent his remaining 21 years in prison. During his time at Alcatraz he got the nickname "Pop Gun Kelly." This was in reference, according to a former prisoner, to the fact that Kelly was a model prisoner and was nowhere near the tough, brutal gangster his wife made him out to be. He spent 17 years on Alcatraz, working in the prison industries, and was quietly transferred back to Leavenworth in 1951. He died of a heart attack at Leavenworth Federal Prison, Kansas on July 18, 1954, his 59th birthday. He is buried at Cottondale Texas Cemetery with a small headstone marked "George B. Kelley 1954".^[5]

In popular culture[link]

• Crime novelist Ace Atkins' 2010 book Infamous is based on the Urschel kidnapping and subsequent multi-state misadventures of George and Kathryn Kelly as they attempted to flee both the FBI and other gangsters eager to claim the Urschel ransom money.
• Machine Gun Kelly and Kathryn Kelly were the inspiration for "Machine Gun Kelly" (1970), a song written by Danny "Kootch" Kortchmar and recorded by James Taylor on his 1971 Album Mud Slide Slim and the Blue Horizon.
• Machine Gun Kelly and his crimes were (loosely) portrayed in the 1958 film Machine-Gun Kelly starring Charles Bronson.
• Machine Gun Kelly is a central character in the 1974 TV film Melvin Purvis: G-Man.
• Kelly is (along with Pretty Boy Floyd and Baby Face Nelson) one of the main characters of the comic book series Pretty, Baby, Machine.
• Punk band the Angelic Upstarts released a single in 1984 titled Machine Gun Kelly.
• Machine Gun Kelly is referenced in the film So I Married an Axe Murderer by Phil Hartman's character while touring Alcatraz.
• In the song "MVP" by the late Harlem rapper Big L, he says: "I run up like Machine Gun Kelly, with a black skully, put one in your belly, leave you smelly, then take your Pelle Pelle."
• In the song "Bluesman" by Harry Chapin, there's a line that goes "No! A fool plays the blues like Machine Gun Kelly, Five hundred notes to the bar...".
• Female Rapper Foxy Brown refers to "Machine Gun Kelly" in her song "Massacre"
• Mentioned in These Animal Men's I'm Not Your Babylon: "Machine Gun Kelly was the first to crack".
• Rapper of the same name from Cleveland, Ohio. See Machine Gun Kelly (rapper).

References[link]

Wikimedia Commons has media related to: Machine Gun Kelly

Further reading[link]

• Hamilton, Stanley (2003). Machine Gun Kelly's Last Stand. University Press of Kansas. ISBN 978-0-7006-1247-5. 
• Atkins, Ace (2010). Infamous. G.P. Putnam's Sons. 
• Dowd, James (April 26, 2010). Book tells tale of capturing infamous Machine Gun Kelly. Memphis Commercial Appeal (newspaper). http://www.commercialappeal.com/news/2010/apr/26/capturing-kelly/. 

External links[link]

• Machine Gun Kelly at Find a Grave
• FBI file on George "Machine Gun Kelly" Barnes

Tinie Tempah
Tempah at the 2010 Way Out West Festival.
Background information
Birth name	Patrick Junior Chukwuemeka Okogwu
Born	(1988-11-07) 7 November 1988 (age 23) Plumstead, London, England
Genres	Grime, Hip hop, drum and bass
Occupations	Rapper, songwriter
Years active	2005–present
Labels	Parlophone, Disturbing London
Associated acts	Labrinth, Ellie Goulding, Swedish House Mafia, Chase & Status, Usher, Kelly Rowland, Eric Turner, Range, Emeli Sandé, Wiz Khalifa, Bei Maejor, Snoop Dogg, Ester Dean, Taio Cruz, Wretch 32, J. Cole, Lupe Fiasco, Rita Ora, Taylor ThePALACE
Website	tinietempah.com

Patrick Chukwuemeka Okogwu^[1] (born 7 November 1988),^[2] better known by his stage name Tinie Tempah, is an English rapper. He made his first mixtape in 2007; his first album, Disc-Overy, debuted at number one in October 2010 and was preceded by two number-one singles.

Early life[link]

Patrick Chukwuemeka Okogwu, was born in London, England on 7 November 1988, and is of Ibusa, Delta State, Nigerian origin. ^[3] He lived on the Aylesbury Estate in South East London until he was 12 with his parents and three younger siblings.^[3] He attended St. Paul's Catholic School in Abbey Wood, London SE2, (now known as St. Paul's Academy). He went on to study A Levels at St Francis Xavier Sixth Form College, SW12. Of his London upbringing, Tempah states: “London is one of the only places in the world where you can live in a council block and see a beautiful semi-detached house across the street. Growing up around that was inspirational, it kept me motivated".^[1]

Career history[link]

Early career[link]

In 2006, Tempah gained a great deal of airplay on British music TV channel, Channel AKA, for his song "Tears" He made his first mixtape in 2007 with 28 songs, freestyles and remixes, featuring Mz Bratt, Chipmunk and G-Unit.^{[citation needed]} His first album, Disc-Overy, debuted at number one in October 2010 and was preceded by the number-one singles "Pass Out" and "Written in the Stars" and the UK Top 5 hits "Frisky" and "Miami 2 Ibiza". In late 2007, he collaborated on a track ("Perfect GCD Hood Economics Room 147") with grime artist Ultra and producers/songwriters Agent X.

Tempah toured with Chipmunk in February 2010. His first break as a musician came when Sony launched its PlayStation Portable (PSP) and used a track entitled "Listen To The Vibe" featuring Yasmin and DJ Ironik, and "Atlantic/Warner" for the futuristic racing game, Wipeout Pure. This resulted in a promotional European tour alongside the likes of Sway and Dizzee Rascal.

Tempah, his manager and cousin Dumi Oburota founded the independent label Disturbing London primarily as an official outlet for Tempah's music, but with the idea of also signing other young artists. According to Dumi: "We wanted to have a platform to put out our music and there wasn't any Def Jam or Roc-A-Fella label equivalent in England. [Also] I wanted to create a major independent label with quality artists. I felt like the major labels had lost the passion for music."^[4] The activities of the label were initially largely funded by student loans and the proceeds from buying and selling cars.^[4]

When scout and music consultant Jade Richardson saw Tempah performing at the 2009 Wireless Festival she called Parlophone Records president Miles Leonard saying: “You’ve got to check out this guy Tinie Tempah. He came on at lunchtime and there’s about 1,000 kids screaming for him. He’s only put out one independent release and he’s got this huge audience.”^[5] Leonard and A&R Nathan Thompson visited Tempah and his manager Dumi at their studio a few weeks later and were hugely impressed to hear about the work they had already done in developing Tempah's career and by the ambitious plans they had for his future.^[5] Leonard told HitQuarters: "I thought it was incredible that an artist and manager were doing so much so soon with so little ... That impressed as much as the music."^[5]

Tempah announced his signing to Parlophone in October 2009 by running a competition on his blog, with the winner invited to High Tea at Claridges to celebrate the deal.^[6]

[edit] 2010–2011: Success and Disc-Overy

Tempah released his debut single "Pass Out" with Parlophone on 28 February 2010, with it entering the UK Singles Chart at number 1. Selling just over 92,000 copies, making this his first number 1 which it remained for two consecutive weeks. Tempah would later perform "Pass Out" on 25 June 2010 at Glastonbury on the Pyramid stage with Snoop Dogg. Tempah then announced his second single, "Frisky", which was released on 6 June 2010 entering the UK Singles Chart at number 2. Tempah supported Rihanna for four dates in May on her 10-date UK tour with Tinchy Stryder and Pixie Lott.^[8] Tempah performed at many summer balls at various universities around the United Kingdom.^{[citation needed]} Tempah performed at Radio 1 Big Weekend in Bangor on 22 May 2010 on the In New Music We Trust stage. He also toured with Mr Hudson in May 2010. Tinie Tempah played the Summertime Ball at Wembley Stadium on 6 June 2010, at Wakestock in Abersoch on 3 July 2010, both T4 on the Beach and the Wireless Festival in London's Hyde Park on 4 July, and V Festival on 21 and 22 August 2010. Tempah released his third single "Written in the Stars" on 19 September 2010. This again charted at number 1 in the UK Singles Chart selling over 115,000 copies in its first week, making it his biggest-selling single to date. The song also went on to chart in a number of other countries. Tempah went on to team up with Swedish House Mafia for his fourth single "Miami 2 Ibiza" which was released on 1 October 2010. This went on to reach a peak of number 4 in the UK Singles Chart and his first number 1 in the Netherlands Mega Single Top 100 chart. He released his long-awaited debut album, Disc-Overy on 4 October 2010 which featured all his previous charted singles.

On 11 October 2010, he kicked off his first UK tour which was supported by Chiddy Bang. He went on to win his first 2 MOBO Awards in October. Tempah also featured on the Tinchy Stryder single "Game Over" which was released on 15 November 2010. This reached number 22 on the UK Singles Chart. On 25 December, Tempah released his fifth single "Invincible" featuring Kelly Rowland, which peaked at number 11 on the UK Singles Chart. "Wonderman", featuring Ellie Goulding, was released and was the fifth official single. Tempah joined Usher on the European leg of his OMG Tour in January 2011. Tempah was also nominated for 4 Brit Awards making him the most nominated artist at the awards. His single "Written in the Stars" was used for a WrestleMania XXVII countdown promo during the WWE PPV Royal Rumble on 30 January 2011. It was later confirmed by WWE that it will be the official theme for Wrestlemania XXVII. It's also the theme song for the 2011 MLB Post Season. On 15 February 2011, he won his first ever Brit Award, for Best British Breakthrough Act. He also won a Brit for Best British Single.^[9] On 7 March 2011, Tempah expressed his desire for his next album to go triple platinum. "I reckon in 2011, towards the end of it, I'm going to do an arena tour – and sell it out – then I reckon I'm going to release another album, and fingers crossed it can go platinum again, and double platinum, and triple. Let's just sell a million."^[10] In early 2011, Tinie Tempah announced a UK Arena tour. Support acts included Nero, Labrinth and Chase and Status (After Party DJ Set).^{[citation needed]} In 2011, Labrinth revealed that Tempah will be releasing "Pass Out" in the United States, featuring a well recognised artist in the American rap game.^[11] On 28 November 2011, Tinie Tempah hosted an episode of the TV show, Never Mind the Buzzcocks.^[12] Also in November, Tinie Tempah released two tracks, "Like It or Love It" which featured both Wretch 32 & J. Cole, and "Lucky Cunt" which featured Big Sean. On 16 December, Tempah released a 9-track mixtape/EP titled Happy Birthday. In early 2012 Tempah featured with Eric Turner and Lupe Fiasco on a track called "Angels and Stars". Tempah's song "Written in the Stars" was used as the entrance song for the New York Giants before Super Bowl XLVI.

[edit] 2012–present: Demonstration

By December 2010 Tempah was writing a second album,^[13] saying there will be a more electronic and live feel to it. It was originally intended for a late 2011 release.^[7][14] but is now scheduled for October 2012.^[15] During an interview, Tempah commented on his second album: "I always like to work with different people on each project I do, just so you get a different sound and angle. I will be working with some of the same people I did for the first album, you know what they say ‘if it ain't broke then don’t try and fix it’."^[16] Tempah hoped to collaborate with other artists; "I really want to collaborate with Toronto's very own Drake. I think he's amazing at what he does. I'd also like to collaborate with Adele, Sleigh Bells, Lykke Li, Dev, James Blake ― those are the few that I'd really like to work with."^[17] Tempah announced in an interview with Rolling Stone that his next single is to be called "Till I'm Gone" which will feature Wiz Khalifa and is produced by Stargate.^[18][19] The single and the video song were released at the end of June 2011.^[20] Tinie Tempah, world renowned drummer Travis Barker and Irish boxing champion Katie Taylor, joined forces to launch Lucozade’s new Yes Campaign, which signals a repositioning of its sports and energy drink brand. Featuring a performance of Tempah's "Simply Unstoppable" with Travis Barker on drums, remixed especially for Lucozade Sport,^{[citation needed]} the campaign was released in Summer 2011.

Tinie Tempah has asked a number of artists to appear on his upcoming second album, including Gary Barlow, Chris Martin, Dizzee Rascal, and The Script.^[21]

At the Brit Awards in 2012, he announced his second album would be called 'Demonstration'.^[22]

Discography[link]

• Disc-Overy (2010)
• Demonstration (2012)

Awards and nominations[link]

References[link]

External links[link]

• Official website

Sean Paul
Sean Paul at the International Reggae and World Music Awards.
Background information
Birth name	Sean Paul Ryan Francis Henriques
Born	(1973-01-09) January 9, 1973 (age 39) Kingston, Jamaica
Genres	Dancehall, reggae, R&B, ragga
Occupations	Musician, singer-songwriter, producer, actor
Years active	1996–present
Labels	VP, Atlantic
Website	allseanpaul.com

Sean Paul Ryan Francis Henriques^[1] (born January 9, 1973),^[1][2] who performs under stage name Sean Paul, is a Jamaican dancehall and reggae artist.

Life and career[link]

1973–96: Early life[link]

Sean Paul was born in Kingston and spent his early years in Upper Andrew Parish, a few miles north of Kingston.^[2] His parents, Garth and Frances, were both talented athletes, and his mother is a well-known painter.^[3] His paternal grandfather was a Sephardic Jew whose family emigrated from Portugal, and his paternal grandmother was Afro-Caribbean; his mother is of English and Chinese Jamaican descent.^[4][5] Sean Paul was raised as a Catholic.^[6] Many members of his family are swimmers. His grandfather was on the first Jamaican men's national water polo team. His father also played water polo for the team in the 1960s, and competed in long-distance swimming, while Sean Paul's mother was a backstroke swimmer. Sean Paul played for the national water polo team from the age of thirteen to twenty-one, when he gave up the sport in order to launch his musical career. He attended the Wolmers High School for Boys, Belair School, Hillel Academy High School, and the College of Arts, Science, and Technology, now known as the University of Technology, where he was trained in commerce with a view to pursuing an occupation in hotel management.

[edit] 1998–2000: Stage One

Sean Paul's manager and producer Jeremy Harding first heard about the singer when his brother told him about seeing someone at a small open mic event in Kingston who sounded a lot like the popular dancehall DJ and toaster Super Cat.^[7] Harding eventually met the singer when Sean Paul came by his studio to ask for some advice. During the meeting Paul recorded a vocal over Harding's rhythm track and in the process created the song "Baby Girl".^[7] Sean Paul began hanging out at the studio every day, and the pair collaborated on several more tracks. When they recorded "Infiltrate" they decided they had something good enough to get on the radio. As Sean Paul started to attract local attention, Harding began looking after his affairs. He later told HitQuarters that his support of Paul's fledgling career initially led him assuming the roles of "DJ, manager, road manager and security guard."^[7] Sean Paul made a quick cameo appearance in the 1998 film Belly on stage performing. He made a very successful collaboration with DMX & Mr. Vegas (Top Shotter) as a soundtrack of the film. In 2000, Sean Paul released his debut album, Stage One with VP Records.

[edit] 2001–02: Dutty Rock

In 2002, he began working extensively with a team of producers and choreographers from Toronto, namely Jae Blaze and Blaze Entertainment and announced the release of his second album, Dutty Rock. Pushed by the success of the singles "Gimme the Light" and the Billboard Hot 100 topper, "Get Busy", the album was a worldwide success, eventually selling over six million copies. Simultaneously, Sean Paul was heard on Beyoncé's U.S. #1 single "Baby Boy" and Blu Cantrell's "Breathe", a chart hit in Europe. Both helped to push his reputation further still in the United States. He appeared on Punk'd, 106 & Park, Sean Paul Respect, Making the Video ("Get Busy", "Gimme the Light", and "Like Glue") and his music videos have been broadcast on MTV and BET. Paul's biggest hits included "Get Busy", "Like Glue", "Gimme the Light", "Baby Boy", and "I'm Still in Love with You".

[edit] 2003–05: The Trinity

Sean Paul in September 2005.

Sean Paul's third album The Trinity was released in on September 27, 2005. The album produced five big hits, "We Be Burnin'", "Ever Blazin'", "Give It Up to Me", "Never Gonna Be The Same" and the U.S. chart-topping smash hit "Temperature". The video of "Give It Up to Me" (featuring Keyshia Cole) was also featured in the movie Step Up in 2006. He was nominated for four awards at the 2006 Billboard Music Awards, including male artist of the year, rap artist of the year, hot 100 single of the year, and pop single of the year for his hit "Temperature".^[8] He also won an American Music Award for "(When You Gonna) Give It Up To Me" beating Kanye West and Nick Lachey who were also nominated for the award. His song "Send It On" from "The Trinity" featured on the 2005 Vauxhall Corsa advert. Sean Paul often contributes his songs to various Riddim Driven albums (by VP Records). In March 2007, he returned to his native Jamaica to perform at the Cricket World Cup 2007 opening ceremony. Sean Paul appears on the game Def Jam: Fight for NY as part of Snoop Dogg's crew and again in the game's sequel, Def Jam Icon.

[edit] 2006–10: Imperial Blaze

The newest Sean Paul album entitled "Imperial Blaze" was released on August 18, 2009. The lead single, “So Fine”, which was produced by Stephen “Di Genius” McGregor, premiered on Sean Paul's official website on April 26, 2009.^{[9][dead link][10]} Speaking to Pete Lewis of 'Blues & Soul' magazine in August 2009, Sean Paul stated that 'Imperial Blaze' "Actually signifies 'The King's Fire'. It's that thing inside of you that gives you the desire to do whatever you do, and be the best in the world at it."^[11] The new album consists of 20 tracks including "So Fine", "Press it Up", "She Want Me", "Private Party" which are party tracks and also love songs such as "Hold My Hand" (feat Keri Hilson), "Lately", "Now That I've Got Your Love" among others. Producers on the album include Don Corleone, Jeremy Harding, and Sean's brother Jason 'Jigzagula' Henriques.^[11] All the full songs of the album have been added to Sean Paul's Myspace page^[12] on the day of release of the album.

Up until now there have been eight music videos: "Always On My Mind (with Da'Ville)", "Give It To You (with Eve)", "Watch Them Roll", "Back It Up" (with Left Side/Mr. Evil), "(I Wanna See You) Push It Baby" (with Pretty Ricky), "Hit 'Em" (with Fahrenheit and his brother Jason "Jigzagula" Henriques), "Come Over" with Estelle,^[13] and also the video of his first single, "So Fine" from the new album. He has recently been featured in Shaggy's video, "Save A Life", which also includes appearances from Elephant Man and Da'Ville, among others. In an effort to raise money for a children's hospital, Shaggy, Sean Paul and others will be having a benefit concert. All proceeds will go towards getting new equipment and technology 'For Aid to the Bustamante Hospital for Children'. In an interview in 2009 he says he is planning to release a new album in 2011. During the premiere for MNET's Big Brother Africa 5: All-Stars on July 18, 2010, he performed his songs "Temperature", "Hold My Hand", and "So Fine".

[edit] 2011–present: Tomahawk Technique

The first single Got 2 Luv U features vocals from American singer Alexis Jordan. It was released on the July 19, 2011 by Atlantic Records. The song was written by Sean Paul, Ryan Tedder and Stargate, and it was produced by Stargate.^[14][15][16]

She Doesn't Mind is the second single from the album. It was written by Sean Paul, Shellback and Benny Blanco and was produced by Shellback and Benny Blanco. It was released on the September 29, 2011 on NRJ & Skyrock (French radios), and to iTunes on October 31.^[17] Like its proceeder, "Got 2 Luv U", featuring Alexis Jordan, it topped the charts in Switzerland, but it debuted at that spot. Sean appeared on the Never Mind the Buzzcocks episode which aired on November 21, 2011.

Sean Paul is featured in the music video for the Simple Plan song Summer Paradise.

Discography[link]

Studio albums

• Stage One (2000)
• Dutty Rock (2002)
• The Trinity (2005)
• Imperial Blaze (2009)
• Tomahawk Technique (2012)

Mixtapes

• The Odyssey Mixtape (2009)

Filmography[link]