Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline; see :Category:Amines for a list of amines. Inorganic derivatives of ammonia are also called amines, such as chloramine (NClH₂).

Compounds with the nitrogen atom attached to a carbonyl of the structure R-C(=O)NR'R'‌' are called amides and have different chemical properties from amines.

Classes of amines

Aliphatic amines

Primary amines arise when one of three hydrogen atoms in ammonia is replaced by an alkyl. Important primary alkyl amines include methylamine, ethanolamine (2-aminoethanol), and the buffering agent tris). Secondary amines have two alkyl substituents bound to N together with one hydrogen. Important representatives include dimethylamine and methylethanolamine. In tertiary amines, all three hydrogen atoms are replaced by organic substituents. Examples include trimethylamine, a distinctively fishy smell. Cyclic amines are either secondary or tertiary amines. Examples of cyclic amines include the 3-member ring aziridine and the six-membered ring piperidine. N-methylpiperidine is a cyclic tertiary amine. It is also possible to have four alkyl substituents on the nitrogen. These compounds are not amines but are called quaternary ammonium cations, have a charged nitrogen center, and necessarily come with an anion.

Aromatic amines

Aromatic amines have the nitrogen atom connected to an aromatic ring as in anilines. The aromatic ring decreases the alkalinity of the amine, depending on its substituents. The presence of an amine group strongly increases the reactivity of the aromatic ring, due to an electron-donating effect.

Naming conventions

Amines are named in several ways. Typically, the compound is given the prefix "amino-" or the suffix: "-amine." The prefix "N-" shows substitution on the nitrogen atom. An organic compound with multiple amino groups is called a diamine, triamine, tetraamine and so forth.

Systematic names for some common amines: {| border="0" align="center" spacing="5" |- valign="top" align="center" | Lower amines are named with the suffix -amine. methylamine | Higher amines have the prefix amino as a functional group. 2-aminopentane(or sometimes: pent-2-yl-amine or pentane-2-amine) |}

Physical properties

Hydrogen bonding significantly influences the properties of primary and secondary amines. Thus the boiling point of amines is higher than those of the corresponding phosphines, but generally lower than those of the corresponding alcohols. For example, methylamine and ethylamine are gases under standard conditions, whereas the corresponding methyl alcohol and ethyl alcohols are liquids. Gaseous amines possess a characteristic ammonia smell, liquid amines have a distinctive "fishy" smell.

Also reflecting their ability to form hydrogen bonds, most aliphatic amines display some solubility in water. Solubility decreases with the increase in the number of carbon atoms. Aliphatic amines display significant solubility in organic solvents, especially polar organic solvents. Primary amines react with ketones such as acetone.

The aromatic amines, such as aniline, have their lone pair electrons conjugated into the benzene ring, thus their tendency to engage in hydrogen bonding is diminished. Their boiling points are high and their solubility in water low

Chirality

Amines of the type NHRR' and NRR'R" are chiral: the nitrogen atom bears four substituents counting the lone pair. The energy barrier for the inversion of the stereocenter is relatively low, e.g., ~7 kcal/mol for a trialkylamine. The interconversion of the stereoisomers has been compared to the inversion of an open umbrella in to a strong wind. Because of this low barrier, amines such as NHRR' cannot be resolved optically and NRR'R" can only be resolved when the R, R', and R" groups are constrained in cyclic structures such as aziridines. Quaternary ammonium salts with four distinct groups on the nitrogen are capable of exhibiting optical activity.

Properties as bases

Like ammonia, amines are bases. Compared to alkali metal hydroxides, amines are weaker (see table for examples of conjugate acid K_a values). The basicity of amines depends on:

# The electronic properties of the substituents (alkyl groups enhance the basicity, aryl groups diminish it). # Steric hindrance offered by the groups on nitrogen. # The degree of solvation of the protonated amine.

The nitrogen atom features a lone electron pair that can bind H⁺ to form an ammonium ion R₃NH⁺. The lone electron pair is represented in this article by a two dots above or next to the N. The water solubility of simple amines is largely due to hydrogen bonding between protons in the water molecules and these lone electron pairs.

Inductive effect of alkyl groups

: +I effect of alkyl groups raises the energy of the lone pair of electrons, thus elevating the basicity. Thus the basicity of an amine may be expected to increase with the number of alkyl groups on the amine. However, there is no strict trend in this regard, as basicity is also governed by other factors mentioned above. Consider the Kb values of the methyl amines given above. The increase in Kb from methylamine to dimethylamine may be attributed to +I effect; however, there is a decrease from dimethylamine to trimethyl amine due to the predominance of steric hindrance offered by the three methyl groups to the approaching Brönsted acid.

Mesomeric effect of aromatic systems

: -M effect of aromatic ring delocalises the lone pair of electrons on nitrogen into the ring, resulting in decreased basicity. Substituents on the aromatic ring, and their positions relative to the amine group may also considerably alter basicity as seen above.

The degree of solvation of protonated amines:

In sterically hindered amines, as in the case of trimethylamine, the protonated form is not well-solvated. For this reason the parent amine is less basic than expected. In the case of aprotic polar solvents (like DMSO and DMF), wherein the extent of solvation is not as high as in protic polar solvents (like water and methanol), the basicity of amines is almost solely governed by the electronic factors within the molecule.

== Synthesis ==

Alkylation

The most industrially significant amines are prepared from ammonia by alkylation with alcohols: :ROH + NH₃ → RNH₂ + H₂O These reactions require catalysts, specialized apparatus, and additional purification measures since the selectivity can be problematic. Treatment of Haloalkanes with amines give the corresponding alkyl-substituted amine, with the release of a halogen acid, which in turn reacts with the amine product or precursor: :RX + 2 R'NH₂ → RR'NH + [RR'NH₂]X Such reactions, which are most useful for alkyl iodides and bromides, are rarely employed because the degree of alkylation is difficult to control.

Reductive routes

Via the process of hydrogenation, nitriles are reduced to amines using hydrogen in the presence of a nickel catalyst. Reactions are sensitive acidic or alkaline conditions, which can cause hydrolysis of -CN group. LiAlH₄ is more commonly employed for the reduction of nitriles on the laboratory scale. Similarly, LiAlH₄ reduces amides to amines. Many amines are produced from aldehydes and ketones via reductive amination, which can use either catalytic hydrogenation or stoichiometric reagents.

Aniline and its derivatives are prepared by reduction of the nitroaromatics. In industry, hydrogen is the preferred reductant, whereas in the laboratory, tin and iron are often employed.

Specialized methods

Many laboratory methods exist for the preparation of amines, many of these methods being rather specialized. {| class="wikitable sortable" style="background-color:white;float: center; border-collapse: collapse; margin: 0em 1em;" border="1" cellpadding="2" cellspacing="0"

! width=200px|Reaction name !! Substrate !! class="unsortable" | Comment |- |valign=top | Gabriel synthesis |valign=top|organohalide | reagent: potassium phthalimide |- |valign=top| Staudinger reduction |Azide | This reaction also takes place with a reducing agent such as lithium aluminium hydride. |- |valign=top| Schmidt reaction |valign=top|carboxylic acid | |- |valign=top| Aza-Baylis–Hillman reaction |valign=top|imine | Synthesis of allylic amines |- |valign=top| Hofmann degradation |valign=top|amide | This reaction is valid for preparation of primary amines only. Gives good yields of primary amines uncontaminated with other amines. |- |valign=top| Hofmann Elimination |valign=top| Quaternary ammonium salt |upon treatment with strong base |- |valign=top| Amide reduction |valign=top| amides | |- |valign=top| Nitrile reduction |valign=top| nitriles | |- |valign=top| Reduction of nitro compounds |valign=top| nitro compounds | can be accomplished with elemental zinc, tin or iron with an acid. |- |valign=top| Amine alkylation |valign=top| haloalkane | |- |valign=top| Delepine reaction |valign=top| organohalide |reagent hexamine |- |valign=top| Buchwald-Hartwig reaction |valign=top| aryl halide | specific for aryl amines |- |valign=top| Menshutkin reaction |valign=top| tertiary amine | reaction product a quaternary ammonium cation |- |valign=top| hydroamination |valign=top| alkenes and alkynes | |- |valign=top| Hofmann-Löffler reaction |valign=top| haloamine | |}

Reactions

Alkylation, acylation, and sulfonation

The dominant reactivity of amines is their nucleophilicity. Most primary amines are good ligands for metal ions to give coordination complexes. Amines are alkylated by alkyl halides. Acyl chlorides and acid anhydrides react with primary and secondary amines to form amides (the "Schotten-Baumann reaction"). Similarly, with sulfonyl chlorides, one obtains sulfonamides. This transformation, known as the Hinsberg reaction, is a chemical test for the presence of amines.

Because amines are basic, they neutralize acids to form the corresponding ammonium salts R₃NH⁺. When formed from carboxylic acids and primary and secondary amines, these salts thermally dehydrate to form the corresponding amides.

Diazotization

Amines react with nitrous acid to give diazonium salts. The most important members are derivatives of aromatic amines such as aniline ("phenylamine") (Ar = aryl or naphthyl): :ArNH₂ + HNO₂ + HX → ArN₂⁺X^- + 2 H₂O

Anilines and naphthylamines form more stable diazonium salts, which can be isolated in the crystalline form. Diazonium salts undergo a variety of useful transformations involving replacement of the N₂ group with anions. For example, cuprous cyanide gives the corresponding nitriles: :ArN₂⁺X^- + Y^- → ArY + N₂ + X^-

Aryldiazonium couple with electron-rich aromatic compounds such as a phenol to form azo compounds, which are widely used as dyes. The alkyl diazonium salts are of little synthetic importance because the diazonium derivatives are too unstable.

Conversion to imines

Imine formation is an important reaction. Primary amines react with ketones and aldehydes to form imines. In the case of formaldehyde (R' = H), these products typically exist as cyclic trimers. : RNH₂ + R'₂C=O → R'₂C=NR + H₂O Reduction of these imines gives secondary amines: : R'₂C=NR + H₂ → R'₂CH-NHR

Similarly, secondary amines react with ketones and aldehydes to form enamines: : R₂NH + R'(R"CH₂)C=O → R"CH=C(NR₂)R' + H₂O

Overview

An overview of the reactions of amine is given below: {| class="wikitable sortable" style="background-color:white;float: center; border-collapse: collapse; margin: 0em 1em;" border="1" cellpadding="2" cellspacing="0"

! width=200px|Reaction name !! Reaction product !! class="unsortable" | Comment |- |valign=top | Amine alkylation |valign=top|amines | degree of substitution increases |- |valign=top | Schotten-Baumann reaction |valign=top|amides | Reagents: acyl chlorides, acid anhydrides |- |valign=top | Hinsberg reaction |valign=top|sulfonamides | Reagents: sulfonyl chlorides |- |valign=top | Amine-carbonyl condensation |valign=top|imines | |- |valign=top | Organic oxidation |valign=top|nitroso compounds | Reagent: peroxymonosulfuric acid |- |valign=top | Organic oxidation |valign=top| diazonium salt | Reagent: nitrous acid |- |valign=top| Zincke reaction |Zincke aldehyde | reagent pyridinium salts , with primary and secondary amines |- |valign=top| Emde degradation |valign=top|tertiary amine | reduction of quaternary ammonium cations |- |valign=top| Hofmann-Martius rearrangement |valign=top|aryl substituted anilines | |- |valign=top| Von Braun reaction |valign=top| Organocyanamide |By cleavage (tertiary amines only) with cyanogen bromide |}

Biological activity

Amines are ubiquitous in biology. The breakdown of amino acids releases amines, famously in the case of decaying fish which smell of trimethylamine. Many neurotransmitters are amines, including epinephrine, norepinephrine, dopamine, serotonin, and histamine. Protonated amino groups (-NH₃⁺) are the most common positively charged moieties in proteins, specifically in the amino acid lysine. The anionic polymer DNA is typically bound to various amine-rich proteins. Additionally, the charged ammonium centers on lysine form salt bridges with carboxylate groups of other amino acids in polypeptides, which influences the three-dimensional structures of proteins.

Application of amines

Dyes

Primary aromatic amines are used as a starting material for the manufacture of azo dyes. It reacts with nitric(III) acid to form diazonium salt, which can undergo coupling reaction to form azo compound. As azo-compounds are highly coloured, they are widely used in dyeing industries, such as:

Methyl orange

Direct brown 138

Sunset yellow FCF

Ponceau

Drugs

Many drugs are designed to mimic or to interfere with the action of natural amine neurotransmitters, exemplified by the amine drugs:

Chlorpheniramine is an antihistamine that helps to relieve allergic disorders due to cold, hay fever, itchy skin, insect bites and stings.

Chlorpromazine is a tranquillizer that sedates without inducing sleep. It is used to relieve anxiety, excitement, restlessness or even mental disorder.

Ephedrine and Phenylephrine, as amine hydrochlorides, are used as decongestants.

Amphetamine, Methamphetamine, and Methcathinone are psychostimulant amines that are listed as controlled substances by the US DEA.

Amitriptyline, Imipramine, Lofepramine and Clomipramine are tricyclic antidepressants and tertiary amines.

Nortriptyline, Desipramine, and Amoxapine are tricyclic antidepressants and secondary amines. (The tricyclics are grouped by the nature of the final amine group on the side chain.)

Gas treatment

Aqueous monoethanolamine (MEA), diglycolamine (DGA), diethanolamine (DEA), diisopropanolamine (DIPA) and methyldiethanolamine (MDEA) are widely used industrially for removing carbon dioxide (CO₂) and hydrogen sulfide (H₂S) from natural gas streams and refinery process streams. They may also be used to remove CO₂ from combustion gases / flue gases and may have potential for abatement of greenhouse gases.

Safety

Low molecular weight amines are toxic, and some are easily absorbed through the skin. Many higher molecular weight amines are highly active biologically.

External links

Primary amine synthesis - Synthetic protocols from organic-reaction.com

See also

IUPAC nomenclature for the official naming rules for amines.

Biogenic amine

Imine

Acid-base extraction

Amine gas treating

References

*

Caption	Nielsen in October 2008
Birth name	Leslie William Nielsen
Birth date	February 11, 1926
Birth place	Regina, Saskatchewan, Canada
Death date	November 28, 2010
Death place	Fort Lauderdale, Florida, U.S.
Death cause	Pneumonia
Occupation	Actor
Nationality	Canadian-American
Years active	1948–2010
Relatives	Erik Nielsen (brother)Jean Hersholt (half-uncle)
Spouse	Monica Boyer (1950–1956)Alisande Ullman (1958–1973)Brooks Oliver (1981–1983)Barbaree Earl (2001–2010)

Leslie William Nielsen, OC (11 February 1926 28 November 2010) was a Canadian and naturalized American actor and comedian. Nielsen appeared in more than one hundred films and 1,500 television programs over the span of his career, portraying more than 220 characters. Born in Regina, Saskatchewan, Nielsen enlisted in the Royal Canadian Air Force and worked as a disc jockey before receiving a scholarship to Neighborhood Playhouse. Making his television debut in 1948, he quickly expanded to over 50 television appearances two years later. Nielsen made his film debut in 1956, and began collecting roles in dramas, westerns, and romance films. Nielsen's performances in the films Forbidden Planet (1956) and The Poseidon Adventure (1972) received positive reviews as a serious actor, though he is primarily known for his comedic roles.

Although Nielsen's acting career crossed a variety of genres in both television and films, his deadpan delivery in Airplane! (1980) marked a turning point in his career, one that would make him, in the words of film critic Roger Ebert, "the Olivier of spoofs." Nielsen enjoyed further success with The Naked Gun film series (1988 1994), based on a short-lived television series Police Squad! in which he starred earlier. His portrayal of serious characters seemingly oblivious to (and complicit in) their absurd surroundings gave him a reputation as a comedian. In the final years of his career, Nielsen appeared in multiple spoof and parody films, many of which were met poorly by critics, but performed well in box office and home media releases. Nielsen married four times and had two daughters from his second marriage. He was recognized with a variety of awards throughout his career, and was inducted into the Canada and Hollywood Walks of Fame.

Early life

(pictured here in the 1936 film His Brother's Wife) inspired him to become an actor.]] Nielsen was born on 11 February 1926 in Regina, Saskatchewan. His mother, Mabel Elizabeth (née Davies), was a Welsh immigrant from Fulham, London, and his father, Ingvard Eversen Nielsen, was a Danish-born Constable in the Royal Canadian Mounted Police.

Nielsen had two brothers; his older brother, Erik Nielsen (1924–2008), was Deputy Prime Minister of Canada during the 1980s. Ingvard was a troubled man who beat his wife and sons, and Leslie longed to escape. As soon as he graduated from high school at 17, he joined the Royal Canadian Air Force, even though he was legally deaf (he wore hearing aids most of his life).

His half-uncle, Jean Hersholt, was an actor best known for his portrayal of Dr. Christian in the long-running radio series of the same name and the subsequent television series and films. In a 1994 Boston Globe article, Nielsen explained, "I did learn very early that when I would mention my uncle, people would look at me as if I were the biggest liar in the world. Then I would take them home and show them 8-by-10 glossies, and things changed quite drastically. So I began to think that maybe this acting business was not a bad idea, much as I was very shy about it and certainly without courage regarding it. My uncle died not too long after I was in a position to know him. I regret that I had not a chance to know him better." At the age of 17, following his graduation from Victoria Composite High School in Edmonton, Nielsen enlisted in the Royal Canadian Air Force and was trained as an aerial gunner during the latter part of World War II (but was too young to be fully trained or sent overseas). He worked briefly as a disc jockey at a Calgary, Alberta radio station, before enrolling at the Lorne Greene Academy of Radio Arts, Toronto. While studying in Toronto, Nielsen received a scholarship to the Neighborhood Playhouse. He noted, "I couldn't refuse, but I must say when you come from the land of the snow goose, the moose and wool to New York, you're bringing every ton of hayseed and country bumpkin that you packed. As long as I didn't open my mouth, I felt a certain security. But I always thought I was going to be unmasked: 'OK, pack your stuff.' 'Well, what's the matter?' 'We've discovered you have no talent; we're shipping you back to Canada.'" Afterward, he attended the Actors Studio, until making his first television appearance in 1948 on an episode of Studio One, alongside Charlton Heston, for which he was paid US$75. appearing in almost 50 live programs in 1950 alone. His distinct voice narrated several documentaries and commercials but, with a handful of exceptions, his early work as a dramatic actor was uneventful. In 1956 he made his feature film debut in the Michael Curtiz-directed musical film The Vagabond King. In the Seattle Post-Intelligencer, Nielsen pointed out that he remembers Curtiz as "a sadist, a charming sadist, but a sadist". Though the film was not a box office success, Nielsen caught the eye of producer Nicholas Nayfack who offered him an audition for a role in the science fiction film Forbidden Planet, resulting in Nielsen being signed to a long-term contract by Metro-Goldwyn-Mayer (MGM).

, in his second film, Forbidden Planet (1956). Nielsen: "Supposedly a science fiction version of Shakespeare's The Tempest, it was all about the id, or something like that. Who knows? The Trekkies today regard it as the forerunner of Star Trek. I just had to wear a tight uniform and make eyes at Anne Francis. I was pretty thin back then."]] Forbidden Planet became an instant success, and roles in other MGM films such as Ransom! (1956), The Opposite Sex (1956) and Hot Summer Night (1957) followed. In 1957 he won the lead role opposite Debbie Reynolds in the romantic comedy Tammy and the Bachelor, which, as a Chicago Tribune critic wrote in 1998, made people consider Nielsen as both a dramatic actor and a handsome romantic lead. However, dissatisfied with the quality of the films he was offered, calling the studios " a Tiffany, which had forgotten how to make silver", Nielsen left MGM, but not before auditioning for the role of Messala in the 1959 historical piece Ben-Hur. Stephen Boyd was eventually given the role. After leaving the studios, Nielsen landed the lead role in the Disney miniseries The Swamp Fox, as American Revolutionary War hero Francis Marion. Eight episodes were produced and aired between 1959 and 1961.

His television appearances include parts in Justice, Alfred Hitchcock Presents, The Virginian, and The Wild Wild West. In 1961, he was the lead in a taut Los Angeles police drama called The New Breed. In 1968, he had a major role in the pilot film for the popular police series Hawaii Five-O, and later appeared in one of the seventh season episodes. In 1969, he had the leading role as a police officer in .

In 1972, Nielsen appeared as the ship's captain in the all-star disaster epic The Poseidon Adventure. He also starred in the William Girdler-directed 1977 action film Project: Kill. His last role before portraying mainly comedy roles was the Canadian disaster film City on Fire in which he played a corrupt mayor. In 1980, he guest starred as Sinclair on the CBS miniseries The Chisholms.

Airplane! and The Naked Gun

Nielsen's supporting role in 1980's Airplane! was a major watershed in his career. The ethos of the movie, a parody of dramatic disaster films such as Zero Hour! and Airport, is largely based on building a comedy around actors who were then known exclusively for their dramatic roles (other stars included Robert Stack, Peter Graves, and Lloyd Bridges). Nielsen was the movie's linchpin, his deadpan delivery contrasting with the continual absurdity surrounding him. When asked, "Surely you can't be serious?", he responds with a curt, "I am serious. And don't call me Shirley." In several interviews he later reflected on the significance of the comedic line: "I thought it was amusing, but it never occurred to me that it was going to become a trademark. It's such a surprise...the thing comes out, people say, 'What did he say?!'" Nielsen also stated that he was "...pleased and honoured that [he] had a chance to deliver that line." The American Film Institute also included the film in its list of the top ten comedy films of all time.

Critics praised the film, which also proved to be a success with audiences. The film's directors, Jim Abrahams, David Zucker, and Jerry Zucker, chose Nielsen for the role based on his ability to play "a fish in water", stating that "You could have cast funny people and done it with everybody winking, goofing off, and silly...we wanted people to be oblivious to the comedy."

The directors, interested in the success of the new comedy, decided to bring a similar style of comedy to television, casting Nielsen in the lead role in their new series, Police Squad!. The series introduced Nielsen as Frank Drebin, the stereotypical police officer modeled after serious characters in earlier police TV series.

Police Squad's opening sequence was based on the 1950s cop show M Squad, (which starred Lee Marvin), which opened with footage of a police car roving through an after-dark urban setting with a big band playing a jazz theme song in the background. The voice-over and the show's organization into "acts" with an epilogue was homage to Quinn Martin police dramas including The Fugitive, The Streets of San Francisco, Barnaby Jones, The F.B.I., and Cannon. Much like in Airplane!, Nielsen portrayed a serious character whose one-liners appeared accidental next to the pratfalls and sight gags around him. Although the show was quickly canceled, lasting only six episodes after being juggled between time slots, Nielsen received an Emmy Award nomination for Outstanding Lead Actor in a Comedy Series.

Non-comedic roles included Prom Night (1980) and Creepshow (1982), both horror films. His last dramatic role was as Allen Green, a violent john killed in self-defense by Barbra Streisand's prostitute character, Claudia Draper, in Martin Ritt's courtroom drama Nuts (1987).

Six years after the cancellation of Police Squad!, its directors decided to make a feature length version for theaters. Titled . The film returned Nielsen to his role as Frank Drebin. It involved a comical scheme of a ruthless drug kingpin using hypnosis in an attempt to assassinate Queen Elizabeth II. Drebin, like the doctor in Airplane!, seemed unaware of the absurdity around him even when unintentionally contributing toward it. Nielsen later said in an interview that he had done many of his own stunts, "You have an idea of how you're going to do something, and it's your vision... unless you do it, it really doesn't stand a chance." Ebert's 3½–star review (out of four) noted, "You laugh, and then you laugh at yourself for laughing."

The Naked Gun spawned two sequels: (1991) and (1994). Naked Gun 2½ grossed more than the original, with $86,930,400, while Naked Gun 33⅓ grossed $51,132,600 in receipts. Nielsen remained open to the prospects of acting in a fourth Naked Gun film, although he doubted that it would ever be produced—"I don't think so," he said in 2005. "If there hasn't been one by now, I doubt it. I think it would be wonderful."

Nielsen briefly appeared on the World Wrestling Federation program in the summer of 1994 on Monday Night RAW; capitalizing on his Frank Drebin character, Nielsen (and George Kennedy) were hired as "super-sleuths" to unravel the mystery of The Undertaker who had disappeared at January's Royal Rumble event. At SummerSlam 1994, in a Naked Gun parody, they were hot on the case (in fact, they were literally standing on a case). Although they did not actually find The Undertaker, the case had been closed (the literal case had been shut) and thus, they solved the mystery.

Later comedies

Nielsen attempted a variety of similar roles with none achieving the prominence of Frank Drebin. These films mostly emulated the style of The Naked Gun series with varying degrees of critical and commercial success: many were panned by critics and most performed poorly. In 1986, Nielsen played against recent type as a dramatic (and unsympathetic) character in the comedy, Soul Man. In 1990, Nielsen also appeared as a Frank Drebin-style character in a series of advertisements in the United Kingdom for Red Rock Cider.

Although The Naked Gun series parodied police dramas in general, Nielsen's later parody films focused on specific targets. Critics panned Repossessed (1990) and (2001), parodies of The Exorcist and , respectively. Both films attempted the absurdist comedy Nielsen is recognized for, but were poorly received. Even a leading role in a Mel Brooks comic horror parody, , failed to generate much box office excitement, although it did gain somewhat of a following on its later release to video. Both 1996's Spy Hard and 1998's Wrongfully Accused, a parody of James Bond films and The Fugitive, respectively, received more popularity on home video but were not well-received by critics.

His attempt at children's comedies met with additional criticism. Surf Ninjas (1993) and Mr. Magoo (1997) faced scathing reviews. Several critics were disappointed that Nielsen's role in Surf Ninjas was only "an extended cameo" and film critic Chris Hicks recommended that viewers "...avoid any comedy that features Leslie Nielsen outside of the Naked Gun series." Jeff Miller of the Houston Chronicle panned Mr. Magoo, a live action remake of the 1950s cartoon, by saying, "I'm supposed to suggest how the film might be better but I can't think of anything to say other than to make the film again."

Nielsen's first major slapstick success since The Naked Gun came in a supporting role in Scary Movie 3 (2003). His appearance as President Harris proved popular enough for a second appearance in its sequel, Scary Movie 4 (2006). This became the first time Nielsen reprised a character since his appearances as Frank Drebin. In one scene, Nielsen appeared almost fully nude, and one critic referred to the scene as putting "the 'scary' in Scary Movie 4."

Nielsen also hosted a series of instructional golf videos beginning with 1993's Bad Golf Made Easier. The videos were not serious, instead combining absurdist comedy with golf techniques. The series were popular enough to spawn two additional sequels, Bad Golf My Way (1994) and Stupid Little Golf Video (1997). Nielsen also co-wrote a fictional autobiography titled The Naked Truth. The book portrayed Nielsen as a popular actor with a long history of prestigious films.

Final years

in Bethlehem, Pennsylvania.]] Even in his eighties, Nielsen continued to have an active career. He performed serious roles on screen and stage (such as his one-man theatre show Darrow, in which he played Clarence Darrow), as well as providing voice-overs and on-camera appearances for commercials; cartoons like Zeroman where he had the leading role/voice; children's shows, such as Pumper Pups, which he narrated, in addition to comedic film roles. The sibling relationship with his elder brother, the Honourable Erik Nielsen, a former Deputy Prime Minister of Canada, served as the premise of an HBO mockumentary entitled The Canadian Conspiracy in which Leslie Nielsen appeared, along with other prominent Canadian-born media personalities. He was a celebrity contestant on CBS's Gameshow Marathon, where he played The Price is Right, Let's Make a Deal, Beat the Clock, and Press Your Luck for charity.

In 2007, Nielsen starred in the drama Music Within. In 2008, he portrayed a version of Uncle Ben for Superhero Movie, a spoof of superhero films. He then appeared in the 2008 parody film An American Carol, which David Zucker directed, produced, and co-wrote. He appeared in the 2009 parody Stan Helsing. Nielsen portrayed the Doctor in the Spanish horror comedy Spanish Movie, a spoof comedy like Scary Movie, but making fun of popular Spanish films.

Nielsen appeared in over 100 films and 1,500 television programs over the span of his career, portraying over 220 characters.

Personal life

Nielsen married four times: Monica Boyer (1950–1956), Alisande Ullman (1958–1973), Brooks Oliver (1981–1983) and Barbaree Earl (2001–2010; his death). Nielsen had two daughters from his second marriage, Maura and Thea Nielsen. Nielsen joked about his view on golf, "I have no goals or ambition. I do, however, wish to work enough to maintain whatever celebrity status I have so that they will continue to invite me to golf tournaments." He was legally deaf and wore hearing aids for most of his life.

Death

In November 2010, Nielsen was admitted to a Fort Lauderdale, Florida hospital for treatment of pneumonia. On 28 November, Doug Nielsen, Nielsen's nephew, announced to the CJOB radio station that Nielsen had died in his sleep, due to complications from pneumonia, around 5:30 pm EST, surrounded by family and friends. As a final bit of humor, Nielsen chose "Let 'er Rip" as his epitaph.

Achievements

Among his numerous awards, in 1995 Leslie Nielsen received UCLA's Jack Benny Award for his comedic roles. In 2001 he was inducted into Canada's Walk of Fame. The following year he was made an Officer of the Order of Canada, although he was also a naturalized U.S. citizen.

On 20 February 2002, Nielsen was named an honorary citizen of West Virginia and an "Ambassador of Mountain State Goodwill". Nielsen visited the state many times to speak and visit friends. In 2003, in honor of Nielsen, Grant MacEwan College named its school of communications after him. Also in 2003, the Alliance of Canadian Cinema, Television and Radio Artists awarded him the ACTRA Award of Excellence. |}

Television

Video

1993: Bad Golf Made Easier

1994: Bad Golf My Way

1997: Stupid Little Golf Video

1997:

Nielsen also appeared in a promotional video for Layman Allen's mathematics game called "Equations"

Writing

1993: The Naked Truth

References

External links

Leslie Nielsen at Box Office Mojo

Leslie Nielsen at Hollywood.com

CBC Digital Archives – Leslie and Erik Nielsen laugh it up

Photographs and literature

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